USA v. Matthew Massi

Filing

PUBLISHED OPINION FILED. [12-51063 Affirmed ] Judge: PRO , Judge: LHS , Judge: JEG Mandate pull date is 08/22/2014 for Appellant Matthew Joseph Massi [12-51063]

Case: 12-51063

Document: 00512719470

Page: 1

Date Filed: 08/01/2014

IN THE UNITED STATES COURT OF APPEALS
FOR THE FIFTH CIRCUIT
United States Court of Appeals
Fifth Circuit

No. 12-51063

FILED
August 1, 2014
Lyle W. Cayce
Clerk

UNITED STATES OF AMERICA,
Plaintiff - Appellee

v.
MATTHEW JOSEPH MASSI,

Defendant - Appellant

Appeal from the United States District Court
for the Western District of Texas
Before OWEN, SOUTHWICK, and GRAVES, Circuit Judges.
LESLIE H. SOUTHWICK, Circuit Judge:
Matthew Joseph Massi was arrested and charged with possession of
marijuana with intent to distribute in violation of 21 U.S.C. § 841. He moved
to suppress evidence uncovered during his detention by law enforcement
officers.

The district court denied the motion.

Massi later entered a

conditional plea agreement, preserving his right to appeal the district court’s
denial of his motion to suppress. We AFFIRM.
FACTUAL AND PROCEDURAL HISTORY
Sometime before 6:00 p.m. on May 16, 2012, Massi and Jose Sanchez,
the pilot of a chartered Mooney M20J single-engine airplane, landed at

Case: 12-51063

Document: 00512719470

Page: 2

Date Filed: 08/01/2014

No. 12-51063
Midland International Airport in Midland, Texas en route from Las Vegas,
Nevada to Orlando, Florida. At approximately the same time, the Air Marine
Operations Center (“AMOC”), a center operating within United States
Customs and Border Protection, set in motion an investigation of the airplane
and its passengers. The explanation of why AMOC acted and what was done
was proffered by Agent Josh Howard, the Government’s witness at the
suppression hearing.

Agent Howard was a criminal investigator in the

Midland office of the Homeland Security Investigations directorate, United
States Immigration and Customs Enforcement, which is within the United
States Department of Homeland Security.

Agent Howard testified that

AMOC, responsible for monitoring all air traffic in the United States, contacted
the Midland Police Department (“MPD”) at 6:00 p.m. to request a “ramp check”
of Massi’s airplane.

A ramp check, as described by Agent Howard, is a

regulatory inspection that can be ordered at any time under regulations of the
Federal Aviation Agency. He described the reach of a ramp check this way:
First and foremost, they will ask for consent to search the
plane. They will ask for identities of all passengers and the pilot.
And with AMOC’s guidance, they will check FAA records. There
should be an actual certificate displayed in the airplane. 1
Agent Howard testified that AMOC informed the agents of three facts
that triggered AMOC’s request for a ramp check: the airplane had flown from
Orlando to Las Vegas, making six refueling stops along the way, stayed in Las
Vegas for about twelve hours, then was returning to Orlando with Midland as
a refueling stop; the registered owner of the airplane had been convicted of

This court once stated that a “ramp check, authorized by state and federal law, permits officers
of the Federal Aviation Administration (“FAA”) or police to examine the pilot’s and aircraft’s licensing
and certification to ensure that they conform to FAA regulations.” United States v. Zukas, 843 F.2d
179, 181 (5th Cir. 1988). Neither party has directed us to current authorizations, by regulation or
otherwise, for ramp checks. Massi has not challenged the ramp check itself by way of refuting its
authorization, scope, or potential duration.

1

2

Case: 12-51063

Document: 00512719470

Page: 3

Date Filed: 08/01/2014

No. 12-51063
drug trafficking approximately twenty years earlier; and the passenger, Massi,
had “recently” crossed from Tijuana, Mexico into the United States, which at
some point was shown to have occurred on May 13, 2012.
Agent Howard’s testimony is a little unclear as to exactly what was
communicated to him by AMOC and when it was communicated.

After

testifying that he was told the three facts, he was asked, “And when they first
told you suspicious flight activity, did they elaborate on that at that amount
[?], or did you have to get that information later?” Howard answered: “I need
to clarify that. I don’t recall if they told me exactly what was going on at the
time, but I did – I did corroborate the information.”
According to Agent Howard, three minutes after AMOC’s 6:00 p.m.
contact, MPD learned that the two men who had flown on the airplane had left
to get food at a Subway sandwich location. When the men landed and then left
for food is unclear. Two MPD officers, apparently stationed that evening at
the airport, were the first to arrive at the aircraft. It is unclear whether Massi
and Sanchez had yet returned. At 6:20 p.m., AMOC contacted the Homeland
Security Investigations directorate. Agents Jerry Garnett and Kris Knight
were dispatched to the airport.

Those two agents thus began their

investigatory work after 6:20 p.m. Agent Howard did not arrive until 7:30 p.m.
The MPD officers questioned Massi and Sanchez prior to the arrival of
the Homeland Security agents.

The officers requested documents and

identification. Sanchez and Massi complied by retrieving documents from
luggage from within the airplane. The luggage was placed on the airplane’s
wing and remained there for the duration of the investigation. Agents Knight
and Garnett arrived after this initial questioning, briefly talked to the MPD
officers, and then questioned Massi and Sanchez. They also made an exterior
examination of the airplane. A canine unit was called at some point to conduct
3

Case: 12-51063

Document: 00512719470

Page: 4

Date Filed: 08/01/2014

No. 12-51063
a sniff of the airplane’s exterior, including the luggage. The canine, Gus, did
not alert. Massi and Sanchez were asked and each denied consent to search
the interior of the airplane. Simultaneous with denying consent to search,
Massi attempted quickly to shut the airplane’s open door. An MPD officer
stopped Massi from doing so and told Massi to stay away from the airplane.
During the inspection of the airplane’s exterior that is authorized under
a ramp check, Agent Knight saw a cardboard box through the window of the
airplane. The box, which was described as measuring “18 to 24 inches across,”
was located behind the rear seat of the airplane. Agent Knight questioned
Massi and Sanchez separately about the box. Sanchez said he had seen Massi
put the box in the airplane. Massi, though, initially denied knowledge of the
box. He first responded to Knight’s question about who owned the box by
saying, “I don’t know what you are talking about.” Asked again, Massi said “I
don’t know of any boxes.” Then, having been told that Sanchez said he had put
the box on the plane, Massi acknowledged that he owned the box and requested
an attorney. At this request, Agent Knight stopped his questioning.
All the events just described occurred prior to Agent Howard’s arrival at
the airport, which was at approximately 7:30 p.m. For the next two hours,
Agent Howard was on the scene “collecting facts about what had transpired”
at the airport prior to his arrival. He did not question Massi or Sanchez, who
were required to remain at the airplane. During this time, Agent Howard’s
office contacted an assistant United States Attorney to obtain guidance for the
investigation. Approval was given to request a search warrant.
Agent Howard left the airport around 9:30 p.m. to return to his office,
which was approximately twenty minutes from the airport by car.

By

10:00 p.m., he began writing the affidavit to support a request for a search
warrant.

Agent Howard also corroborated information that was received
4

Case: 12-51063

Document: 00512719470

Page: 5

Date Filed: 08/01/2014

No. 12-51063
earlier from AMOC. He emailed the affidavit to the United States Attorney’s
office and obtained its approval. He then contacted a federal magistrate judge,
drove to the magistrate judge’s residence, and obtained the signed warrant at
11:30 p.m. Agent Howard returned to the airport with the search warrant at
approximately midnight and conducted a search of the airplane. Nineteen
sealed bags of marijuana with a total weight of 10.50 kilograms were found
within the cardboard box.

Upon this discovery, Massi and Sanchez were

immediately arrested, informed of their rights, and taken into custody.
Massi was charged with possession with intent to distribute marijuana.
He moved to suppress all evidence seized in the search of the airplane as a
product of an illegal arrest and improperly prolonged detention. The district
court denied the motion. Massi pled guilty, conditioned on being allowed to
appeal the validity of the order denying his motion to suppress.
DISCUSSION
In considering a district court’s decision on a motion to suppress, this
court reviews findings of facts for clear error and conclusions of law de novo.
United States v. Rivas, 157 F.3d 364, 367 (5th Cir. 1998). All record evidence
is viewed “in the light most favorable to the party who prevailed in the district
court.” United States v. Cardenas, 9 F.3d 1139, 1147 (5th Cir. 1993). The
district court’s ruling should be upheld “if there is any reasonable view of the
evidence to support it.” United States v. Michelletti, 13 F.3d 838, 841 (5th Cir.
1994) (en banc) (quotation marks omitted).
Massi argues that the district court erred in denying his motion to
suppress because the search warrant relied upon by the officers was the
product of an illegal seizure, namely, his lengthy detention at the airport. He
contends that his detention was without reasonable suspicion, lacked probable
cause, and was of a length that violated the Fourth Amendment. He further
5

Case: 12-51063

Document: 00512719470

Page: 6

Date Filed: 08/01/2014

No. 12-51063
argues that his unconstitutional detention taints evidence obtained as a result
of the search warrant’s execution and that such evidence should be excluded
as fruit of the poisonous tree.
The Government argues that Massi’s detention was appropriate under
the Fourth Amendment because the initial regulatory check was valid. As the
investigation progressed, reasonable suspicion and eventually probable cause
to search arose. The Government denies there was ever an illegal arrest.
Regardless, the Government argues that the good faith exception to the
exclusionary rule would permit the admissibility of any evidence obtained
pursuant to the search warrant because the warrant was obtained and
executed by an officer acting with objective good faith under United States v.
Leon, 468 U.S. 897 (1984).
I. Legality of the Stop and Detention
The district court denied Massi’s motion to suppress. The court held that
there was “initial reasonable suspicion to make the stop and that it developed
into probable cause” justifying continuing the stop.
The Fourth Amendment guarantees individuals the right to be “secure
in their persons, houses, papers, and effects, against unreasonable searches
and seizures.” U.S. CONST. amend. IV. Evidence that was obtained from a
“substantial and deliberate” violation of the Fourth Amendment will be
suppressed and excluded from consideration. Franks v. Delaware, 438 U.S.
154, 171 (1978). This court has recognized that there are different “tiers of
citizen-police contact for purposes of fourth amendment analysis.” United
States v. Zukas, 843 F.2d 179, 181 (1988) (citing United States v. Berry, 670
F.2d 583, 591 (5th Cir. 1982)). The first tier involves “no coercion or detention
and does not implicate the fourth amendment.” Zukas, 843 F.2d at 181. The
6

Case: 12-51063

Document: 00512719470

Page: 7

Date Filed: 08/01/2014

No. 12-51063
second tier, an investigatory stop, “is a brief seizure that must be supported by
reasonable suspicion . . . .” Id. Finally, the third tier is “a full scale arrest
[which] must be supported by probable cause.” Id. at 181-82.
For the purposes of our discussion of Massi’s interaction with law
enforcement, the following chronology is our best understanding of the events
from evidence at the suppression hearing and in the affidavit supporting the
search warrant:
(1)

Massi and Sanchez land the airplane at Midland Airport at or
before 6:00 p.m., then leave to get food.

(2)

AMOC notifies MPD at 6:00 p.m. of the airplane’s arrival and
requests a ramp check.

(3)

MPD officers question Massi and Sanchez, doing so after the latter
return in a rental car from picking up food.

(4)

Homeland Security Agents Knight and Garnett arrive after
6:20 p.m. and begin participating in the ongoing encounter
initiated by MPD.

(5)

The questioning of Massi and Sanchez and the inspection of the
airplane are completed by 7:30 p.m., with canine Gus’s failure to
alert occurring at approximately 7:20 p.m.

(6)

From 7:30 to 9:30 p.m., Massi and Sanchez’s detention continues
as Agent Howard arrives on the scene and gathers information
from the other law enforcement officers.

(7)

From 9:30 to 11:30 p.m., Agent Howard travels to his office,
prepares his affidavit, obtains United States Attorney’s office
approval, presents it to a United States Magistrate Judge at his
residence, and obtains a warrant to search the airplane.

(8)

At midnight, the airplane is searched under the just-issued
warrant.

We now examine the authority of law enforcement officers to detain
Massi and Sanchez during the course of this approximately six-hour period.
A. Ramp Check and Terry Stop

7

Case: 12-51063

Document: 00512719470

Page: 8

Date Filed: 08/01/2014

No. 12-51063
Massi does not argue that the regulatory inspection of a ramp check was
improper. Such a regulatory inspection is not a detention under the justdescribed Berry formulation of citizen-police contact.

Id.

Therefore, we

consider the issue of suppression to turn solely on what occurred after the ramp
check. In so doing, we recognize that no specific occurrence demarks when the
activities relating to the ramp check ended and a broader investigation
commenced. Instead, as the investigation continued for purposes well beyond
the regulatory ones justifying a ramp check, we must apply other relevant legal
authority.
Massi contends that continuing the stop was not based on articulable,
reasonable suspicion as required for an investigatory stop within the second
tier of citizen-police contact. The validity of investigatory stops is governed by
the standard set forth in Terry v. Ohio, 392 U.S. 1 (1968). Police may detain
an individual if the officer has a reasonable suspicion based on specific and
particularized facts that the person is involved in criminal activity. Id. at 2122, 27. Our Terry inquiry involves examining whether the initial action was
justified and, then, determining whether any subsequent action was
reasonably related in scope to either the circumstances that justified the stop
or to dispelling a reasonable suspicion that developed during the stop. United
States v. Brigham, 382 F.3d 500, 506-07 (5th Cir. 2004) (en banc). “Any
analysis of reasonable suspicion is necessarily fact-specific, and factors which
by themselves may appear innocent, may in the aggregate rise to the level of
reasonable suspicion.” United States v. Ibarra-Sanchez, 199 F.3d 753, 759 (5th
Cir. 1999).
The facts leading to a finding of reasonable suspicion do not have to be
based on a law enforcement officer’s personal observation, but can also arise
from the “collective knowledge” of law enforcement entities, so long as that
8

Case: 12-51063

Document: 00512719470

Page: 9

Date Filed: 08/01/2014

No. 12-51063
knowledge gives rise to reasonable suspicion and was communicated between
those entities at the time of the stop. See id. at 759-60.
There is no clear evidence as to the timeline starting with Massi and
Sanchez’s return to the airplane between 6:00 and 6:30 p.m., and the arrival of
Agent Howard at about 7:30 p.m.

The reasonable suspicion arose from

AMOC’s information and was that the airplane was being used to transport
drugs. In evaluating what happened at the scene, our caselaw requires “both
the scope and length of the officer’s investigation to be reasonable in light of
the facts articulated as having created the reasonable suspicion of criminal
activity.” United States v. Pack, 612 F.3d 341, 357 (5th Cir. 2010).
We conclude that sufficient reasonable suspicion existed to justify an
investigatory stop under Terry, which augmented the right to investigate that
arose from the ramp check. AMOC’s suspicions arising from the flight pattern
were augmented by information concerning Massi’s recent travel to Tijuana,
Mexico, a known hub of the illegal drug trade. A third factor was the prior
drug trafficking conviction of the airplane’s registered owner. It is true that
these facts were passed along by AMOC and were not learned as a result of
direct law enforcement contact. Nonetheless, the obligation to submit to a
ramp check allowed the airplane and Massi to be held at the airport initially.
The law enforcement officers then had a proper basis to continue the encounter
beyond the regulatory ramp check under the reasonable suspicion standard in
Terry, even if the facts giving rise to suspicion were known prior to law
enforcement contact with Massi. 2 The suspicion of a drug crime, either having
been committed or still ongoing, was not dispelled and permitted the encounter
to continue beyond the temporal confines of the ramp check.
No argument is made that the ramp check was invalid as pretextual. This court has already
rejected the argument that the motives underlying a ramp check could invalidate what would
otherwise have been a proper inspection. Zukas, 843 F.2d at 182 n.1.

2

9

Case: 12-51063

Document: 00512719470

Page: 10

Date Filed: 08/01/2014

No. 12-51063
B. De Facto Arrest and Probable Cause
Massi next argues that the duration of his detention constituted a de
facto arrest. A detention initially authorized by Terry can, due to its duration,
transform into the equivalent of an arrest. United States v. Zavala, 541 F.3d
562, 579 (5th Cir. 2008). If Massi’s detention continued beyond the bounds
permitted by a finding of reasonable suspicion under Terry, it “must be
accompanied by probable cause” to believe that Massi had committed a
criminal offense. Freeman v. Gore, 483 F.3d 404, 413 (5th Cir. 2007).
1. Terry stop becoming an arrest
We first examine whether Massi’s detention under Terry “morphed . . .
into a de facto arrest” and, if so, when that arrest occurred. Zavala, 541 F.3d
at 579. An arrest occurs when, “in view of all the circumstances surrounding
the incident, a reasonable person would have believed that he was not free to
leave.” United States v. Mendenhall, 446 U.S. 544, 554 (1980). As a factual
matter, we know that Massi and Sanchez were told by law enforcement officers
that they were not free to leave. The issue is solely a legal one.
At the end of the officers’ investigation, the following was known: (1) the
trip had been laborious – six refueling stops – from Orlando to Las Vegas, then
after a 12 hour stop, the return trip began; one of the occupants had just
entered the country through Tijuana, Mexico, a known center of drug activity;
and the owner of the airplane had a more-than-twenty-year-old conviction for
drug trafficking; (2) a canine, Gus, conducted a sniff of the airplane’s exterior
at 7:20 p.m., including the luggage, and did not alert; (3) Massi and Sanchez
complied with all requests, except each denied consent to search the airplane;
(4) when Massi denied consent, he attempted to shut the airplane’s open door;
(5) Agent Knight saw a cardboard box behind the rear seat of the airplane, 18
to 24 inches across in size; (6) Sanchez told Agent Knight he had seen Massi
10

Case: 12-51063

Document: 00512719470

Page: 11

Date Filed: 08/01/2014

No. 12-51063
put the box in the airplane; (7) Massi denied knowing about the box; and (8)
once told what Sanchez said, Massi admitted to owning the box. No further
questioning occurred, because by then Massi had requested an attorney.
The final event in this chronology appears to have been the canine sniff
at 7:20 p.m. Agent Howard arrived at 7:30 p.m. A fair estimate is that Massi
and Sanchez’s encounter with MPD began once they had time to return to their
airplane after getting food, and once the officers had time to arrive at the
airplane upon being told at 6:00 p.m. to conduct a ramp check. The Homeland
Security agents were not informed of the airplane until 6:20 p.m., so their start
was later than that of MPD. It would appear that the encounter had been
underway for about an hour by the time Agent Howard arrived.
We noted above that we review the evidence on a motion to suppress in
a manner favorable to the prevailing party, Cardenas, 9 F.3d at 1147, and
uphold the ruling “if there is any reasonable view of the evidence to support
it.”

Michelletti, 13 F.3d at 841 (quotation marked omitted).

There are

uncertainties in the record regarding the length of time taken by the ramp
check, a check which independently supports the initial activity at the
airplane. We have also found that there were reasonable suspicions of drug
activity supporting some additional inquiry. Therefore, we see no clear factual
error or any legal error in the district court’s ruling that at least at the time
that Agent Howard arrived, no violation of Massi’s Fourth Amendment rights
had occurred.
The remaining concern, of course, is that probable cause to arrest was
absent as of 7:30 p.m., but Massi continued to be detained. The detention
lasted until midnight, four and one-half hours after Agent Howard’s arrival.
From 7:30 to 9:30 p.m., Agent Howard collected and analyzed all facts
uncovered during the regulatory check and Terry investigation.
11

Between

Case: 12-51063

Document: 00512719470

Page: 12

Date Filed: 08/01/2014

No. 12-51063
9:30 p.m. and midnight, Howard went to his office; prepared an affidavit;
talked at least with AMOC, the United States Attorney’s office, and a
Magistrate Judge; procured a search warrant; and returned to search the
airplane’s interior. During all this time, Massi was not free to leave.
This delay existed, ultimately, because law enforcement officers sought
a warrant and warrants take time. A Terry detention “must be temporary and
last no longer than is necessary to effectuate the purpose of the stop, unless
further reasonable suspicion, supported by articulable facts, emerges.”
Brigham, 382 F.3d at 507.

Our caselaw presents numerous examples of

automobile searches, and occasionally searches of airplanes, in which the issue
is whether immediate, warrantless searches were justified by exigent
circumstances. Here, law enforcement officers instead held the airplane and
the occupants until evidence could be corroborated, an affidavit prepared, and
the search warrant obtained. As a result of the delay that accompanied this
process, the initial investigatory stop “morphed from a Terry detention into a
de facto arrest” requiring probable cause. Zavala, 541 F.3d at 579. Though
the ramp check and Terry-justified investigation were over by 7:30 p.m., Massi
had to remain until midnight while a warrant was obtained. Thus, both men
were detained well beyond the time for the ramp check and Terry investigation.
Generally, absent the brief and minimally intrusive detention such as
permitted under Terry, a seizure without probable cause to believe the person
is guilty of a crime violates the Fourth Amendment. Dunaway v. New York,
442 U.S. 200, 210 (1970). “[W]e have never held that a police officer may detain
a defendant for one hour and thirty minutes until a full-blown drug
investigation is completed.” Zavala, 541 F.3d at 580. We conclude that the
justification under Terry to hold Massi had ended by 7:30 p.m. when Agent
Howard arrived. Thereafter, Massi was under arrest.
12

Case: 12-51063

Document: 00512719470

Page: 13

Date Filed: 08/01/2014

No. 12-51063
2. Probable cause for an arrest
Massi’s de facto arrest must be supported by probable cause. “[P]robable
cause is a fluid concept – turning on the assessment of probabilities in
particular factual contexts – not readily, or even usefully, reduced to a neat set
of legal rules.” Illinois v. Gates, 462 U.S. 213, 232 (1983). “We must also be
mindful that probable cause is the sum total of layers of information and the
synthesis of what the police have heard, what they know, and what they
observed as trained officers. We weigh not individual layers but the laminated
total.” United States v. Edwards, 577 F.2d 883, 895 (5th Cir. 1978) (en banc)
(quotation marked omitted).
The facts and circumstances known to law enforcement by the time of
Agent Howard’s 7:30 p.m. arrival were all that was known until the midnight
search of the airplane. Officers at the scene knew that the airplane had
displayed suspicious flight activity; that the airplane’s owner had a prior
conviction for drug trafficking; and that Massi had acknowledged traveling
from Tijuana, Mexico into the United States three days before the airplane left
Las Vegas, Nevada. As the investigation progressed, these officers witnessed
Massi’s attempt to close the airplane door after his denial of consent to search,
the existence of a cardboard box behind the rear seat of the airplane, and
Massi’s inconsistent statements as to his knowledge and ownership of the box.
The question for us is whether such evidence constituted probable cause to
arrest Massi and keep him at the airport in excess of four more hours. The
Government has primarily argued that this evidence supports probable cause
to search the aircraft. That is a separate question that we discuss later.
Zavala is again instructive. Finding probable cause absent there, we
noted: “Although [the defendant and his passenger] gave conflicting answers
to several interview questions, this could not serve as the catalyst to convert
13

Case: 12-51063

Document: 00512719470

Page: 14

Date Filed: 08/01/2014

No. 12-51063
mere reasonable suspicion into probable cause.” Zavala, 541 F.3d at 575
(quotation marks omitted). While we do not require new facts be developed in
order to transform reasonable suspicion into probable cause, we do require that
“the totality of facts and circumstances within a police officer’s knowledge at
the moment of arrest are sufficient for a reasonable person to conclude that the
suspect had committed, or was in the process of committing, an offense.”
Zavala, 541 F.3d at 575. There needed to be probable cause to believe that
Massi was guilty of a drug-related offense, but we conclude that until the
midnight search, all the officers had were suspicions.
We conclude that Massi was subject to an unconstitutional seizure at the
airport. The issue on appeal, though, is not the existence of a constitutional
violation in isolation but whether the evidence obtained as a result of the
midnight search pursuant to a warrant should be suppressed. To link the
unconstitutional seizure to the eventual search, Massi argues that the search
warrant was the fruit of a tree poisoned by the unconstitutional detention. The
Government argues that the detention is irrelevant, as the search that
discovered the evidence, undertaken pursuant to a warrant, was valid at a
minimum under the good faith exception to the exclusionary rule. We now
turn to the resolution of those competing views.
II. Interaction of Good Faith Exception and Fruit of the Poisonous Tree Doctrine
The good faith exception to the exclusionary rule provides that “evidence
obtained during the execution of a warrant later determined to be deficient is
nonetheless admissible if the executing officer’s reliance on the warrant was
objectively reasonable and made in good faith.” United States v. Woerner, 709
F.3d 527, 533 (5th Cir. 2013) (citing Leon, 468 U.S. at 921-25). Applying the
good faith exception does not resolve whether a constitutional right has been
14

Case: 12-51063

Document: 00512719470

Page: 15

Date Filed: 08/01/2014

No. 12-51063
violated; it simply is a judicial determination that exclusion of evidence does
not advance the interest of deterring unlawful police conduct. Leon, 468 U.S.
at 906-07 (citing Gates, 462 U.S. at 223). In effect, the good faith exception
limits the remedy of exclusion where “the marginal or nonexistent benefits
produced by suppressing evidence obtained in objectively reasonable reliance
on a subsequently invalidated search warrant cannot justify the substantial
costs of exclusion.” Leon, 468 U.S. 922.
Typically, this court conducts a two-step review of a district court’s
denial of a motion to suppress evidence seized under a warrant. United States
v. Pena-Rodriguez, 110 F.3d 1120, 1129 (5th Cir. 1997). “The first step requires
the court to determine whether the good-faith exception to the exclusionary
rule applies.” Id. “The second step requires the court ‘to ensure that the
magistrate had a substantial basis for . . . concluding that probable cause
existed.’” Id. (quotation marks omitted). “If the good-faith exception applies,
the court need not reach the question of probable cause.” Id. at 1130 (citations
omitted). “Principles of judicial restraint and precedent dictate that, in most
cases, we should not reach the probable cause issue if . . . the good-faith
exception of Leon will resolve the matter.” United States v. Craig, 861 F.2d
818, 820 (5th Cir. 1988). In this appeal, we are presented with different
circumstances from those traditionally animating this two-step analysis. The
Government is asking us to determine whether the good faith exception to the
exclusionary rule applies when the search warrant was used on an airplane
whose pilot and passenger had several hours earlier been seized in violation of
their Fourth Amendment rights.
The question of whether the good faith exception can permit the
admissibility of evidence over a possible taint caused by an earlier-in-time
detention in violation of the Fourth Amendment that would otherwise warrant
15

Case: 12-51063

Document: 00512719470

Page: 16

Date Filed: 08/01/2014

No. 12-51063
exclusion as fruit of the poisonous tree, is not territory frequented in our
jurisprudence. 3 We recently discussed whether the good faith exception is
applicable when “the magistrate’s probable cause finding is based on evidence
that was the product of an illegal search or seizure.” Woerner, 709 F.3d at 534.
There, the court considered whether evidence obtained as a result of the
execution of a search warrant should be suppressed where the affidavit
included information gained from a defendant during a custodial interrogation
that was later suppressed as the fruit of an earlier-in-time, unlawful search.
Id. Both the interrogation and unlawful search were undertaken by a different
law enforcement entity than that of the officers who pursued the search
warrant at issue; the two investigations were parallel and the officers seeking
the search warrant did not know of the other officer. Id. Such separation did
not exist here between the improper detention and the processing of the search
warrant.
Also relevant to Woerner’s analysis was an assessment of the objective
good faith of the law enforcement officer in pursuing the warrant. See id. We
concluded, under the circumstances presented, that suppression was not
justified and that the good faith exception applied. Id. at 535. While differing
from Massi’s scenario in both the context – an unlawful search – and the
existence of a parallel investigation, Woerner signals an openness to applying
the good faith exception where an earlier-in-time constitutional violation exists
alongside a search warrant that was sought and executed in good faith.

We say “possible taint” because there is not a clear causal connection between the
unconstitutional detention and the acquisition of evidence used to support the search warrant. We
have found that the evidence used to obtain the search warrant was acquired but not fully corroborated
for the purposes of Agent Howard’s affidavit prior to the improper detention. The unconstitutional
detention did allow the plane and its occupants still to be at the airport for the midnight warrant to
be executed, so there is that clear link. We will discuss the issue as if the fruit of poisonous tree
doctrine applies.
3

16

Case: 12-51063

Document: 00512719470

Page: 17

Date Filed: 08/01/2014

No. 12-51063
We will discuss the details of the good faith exception momentarily. To
understand Woerner, though, we need to give a brief summary of those
principles.

The Supreme Court in Leon identified four situations, or

“exceptions,” that would prevent admission of evidence obtained through a
search warrant: the affiant misled the magistrate who issued the warrant; the
magistrate “abandoned his judicial role”; the affidavit is patently inadequate
to show probable cause; or the warrant is so deficient on its face that officers
could not presume its validity. Leon, 468 U.S. at 921-25. The Woerner court
stated that the facts of that case required it “to answer whether the good faith
exception applies in a fifth situation: when the magistrate’s probable cause
finding is based on evidence that was the product of an illegal search or
seizure.” Woerner, 709 F.3d at 534. The court did not answer the question of
whether a fifth exception should be recognized. Instead it held that the facts
did not support that the magistrate had acted on information that was tainted:
“the police misconduct leading to the inclusion of [the illegally obtained
statements in the] warrant application was at most the result of negligence of
one or more law enforcement officers.” Id. at 534-35. As we will discuss later,
we conclude that a preferable way to consider facts such as these is not as a
fifth exception but as a corollary to the first exception – did the affiant mislead
the magistrate?
The dissent notes distinctions between Woerner and the current case,
and from those distinctions concludes that a different result is required.
Distinctions do not always make a difference, and these do not. It is true that
Agent Howard and his agency, ICE, were involved throughout that evening,
while in Woerner there were two different though parallel investigations by
different officers. The observation is made in Woerner that “if the officer
applying for the warrant knew or had reason to know that the information was
17

Case: 12-51063

Document: 00512719470

Page: 18

Date Filed: 08/01/2014

No. 12-51063
tainted . . . then suppressing the evidence seized pursuant to the warrant
‘pay[s] its way by deterring official lawlessness.’” Woerner, 709 F. 3d at 534
(quoting Gates, 462 U.S. at 258 (White, J. concurring)). As we will discuss, we
do not agree that Agent Howard’s knowledge of what transpired at the airport
equates to knowledge that what occurred was unconstitutional. We will also
discuss that Agent Howard’s affidavit disclosed the basic facts of the delay,
that delay being the source of the alleged taint to the later search. There was
no misleading of the magistrate.
Other circuits have considered similar scenarios. The Sixth, Second, and
Eighth Circuits have concluded that in certain circumstances, the good faith
exception can overcome a taint from prior unconstitutional conduct.

See

United States v. McClain, 444 F.3d 556, 564-566 (6th Cir. 2005) (finding that
“the Leon good faith exception should apply despite an earlier Fourth
Amendment violation”); United States v. Fletcher, 91 F.3d 48, 51-52 (8th Cir.
1996) (finding that the Leon exception was applicable to a subsequent warrantauthorized search of luggage when the initial detention of the luggage was a
Fourth Amendment violation); United States v. Thomas, 757 F.2d 1359, 1368
(2d Cir. 1985) (finding Leon applicable to a warrant-authorized search of an
apartment where the affidavit supporting the warrant contained evidence
obtained in violation of the Fourth Amendment). The Ninth and Eleventh
Circuits, though, have held that the good faith exception does not apply where
a search warrant is issued on the basis of evidence that is fruit of the poisonous
tree. See United States v. McGough, 412 F.3d 1232, 1239-40 (11th Cir. 2005);
United States v. Vasey, 834 F.2d 782, 789-90 (9th Cir. 1987).
One of the recent cases to address this issue is persuasive. See McClain,
444 F.3d 556. There, the Sixth Circuit stated that it must “reconcile the ‘good
faith’ exception established in Leon . . . with the ‘fruit of the poisonous tree’
18

Case: 12-51063

Document: 00512719470

Page: 19

Date Filed: 08/01/2014

No. 12-51063
doctrine first coined in Nardone v. United States, 308 U.S. 338, 341 (1939).”
Id. at 564. “[P]articularly instructive” was the Eighth Circuit’s explanation of
Leon that “evidence seized pursuant to a warrant, even if in fact obtained in
violation of the Fourth Amendment, is not subject to the exclusionary rule if
an objectively reasonable officer could have believed the seizure valid.”
McClain, 444 F.3d at 566 (quoting United States v. White, 890 F.2d 1413, 1419
(8th Cir. 1989)). As in the Eighth Circuit’s decision, the McClain court “refused
to apply the exclusionary rule because the facts surrounding the initial Fourth
Amendment violation were ‘close enough to the line of validity to make the
officer’s belief in the validity of the warrant objectively reasonable.’” McClain,
444 F.3d at 566 (quoting White, 890 F.2d at 1419).
In McClain, officers had responded to a neighbor’s call about a light on
in a house that was supposed to be unoccupied; after initial inspection outside
discovered an open door, the officers entered the house to determine if there
had been an intruder. Id. at 560. That entry, which uncovered evidence of a
marijuana grow operation but no drugs themselves, was later found to be
invalid. Id. at 561. The evidence formed the basis for an investigation, search
warrant, and later entry that uncovered 348 marijuana plants and growing
equipment. Id. at 560. The Sixth Circuit found that the good faith exception
applied to permit the admissibility of evidence obtained as a result of the
search warrant’s execution despite the taint that resulted from the
unconstitutional initial entry of the house. Id. at 566. In considering that
initial entry, the McClain court concluded that it “did not believe that the
officers were objectively unreasonable” in believing that criminal activity was
afoot and there was “no evidence that the officers knew they were violating the
Fourth Amendment” in conducting their warrantless activity. Id. The court
emphasized that, “importantly, the officers who sought and executed the
19

Case: 12-51063

Document: 00512719470

Page: 20

Date Filed: 08/01/2014

No. 12-51063
search warrants were not the same officers who performed the initial
warrantless search, and [the officer’s] warrant affidavit fully disclosed to a
neutral and detached magistrate the circumstances surrounding the initial
warrantless search.” Id. The court determined:
Because the officers who sought and executed the warrants acted
with good faith, and because the facts surrounding the initial
warrantless search were close enough to the line of validity to
make the executing officers’ belief in the validity of the search
warrants objectively reasonable, we conclude that despite the
initial Fourth Amendment violation, the Leon exception bars
application of the exclusionary rule in this case.
Id.

We adopt the following reasoning, drawing on McClain, as our

understanding of the interaction of the doctrine of fruit of the poisonous tree
with Leon’s good faith exception, as each apply to evidence obtained as the
result of the execution of a search warrant. Two separate requirements must
be met for evidence to be admissible: (1) the prior law enforcement conduct that
uncovered evidence used in the affidavit for the warrant must be “close enough
to the line of validity” that an objectively reasonable officer preparing the
affidavit or executing the warrant would believe that the information
supporting the warrant was not tainted by unconstitutional conduct, and (2)
the resulting search warrant must have been sought and executed by a law
enforcement officer in good faith as prescribed by Leon.
The dissent here insists that a necessary element of this interaction
between good faith use of a search warrant and a taint to the evidence
supporting the warrant is that the officers engaged in the prior conduct be
different than those who acquire the warrant. It argues that our review of
McClain makes a “glaring omission” in failing to recognize the importance of
the fact that “the officers who sought and executed the search warrants were
not the same officers who performed the initial warrantless search.” Id. at 566.
20

Case: 12-51063

Document: 00512719470

Page: 21

Date Filed: 08/01/2014

No. 12-51063
We see no basis for creating such a requirement, though the precedents we
have cited have those facts. What is important is that the officer presenting
the information to a magistrate be objectively reasonable in concluding that
the information being used to support the warrant was not tainted. It is not
awareness of the existence of the conduct that later is found to be improper
that is important, but awareness at the time of presenting the affidavit that
the conduct violated constitutional rights that would affect the application of
the good faith exception.
A. Objectively Reasonable Belief in the Validity of Prior Police Conduct
We turn to whether it was objectively reasonable for the officer executing
the search warrant to believe that Massi’s detention was valid. Agent Howard
was the law enforcement officer who sought and executed the search warrant.
Unlike the warrant-seeking officers in McClain, Agent Howard was present
during some of Massi’s detention and, therefore, was present while the
constitutional violation occurred.

We analyze whether an objectively

reasonable officer who assumed a role in an ongoing investigation, obtained a
search warrant, and executed that search warrant would have been aware of
the constitutional invalidity of this detention.
Upon Agent Howard’s 7:30 p.m. arrival at the airport, there was no
reason for him objectively to believe that any improper law enforcement
conduct occurred prior to his arrival. Indeed, we have held that there was no
such conduct. Howard did not initiate and continue the encounter for the
purpose of eventually gaining sufficient new information to use in obtaining a
search warrant. Rather, at 7:30 p.m. he joined a completed investigation
during which no constitutional violation had occurred.
Turning next to whether Agent Howard should have been aware of an
invalidity as a result of continued detention (post-7:30 p.m.) arising from the
21

Case: 12-51063

Document: 00512719470

Page: 22

Date Filed: 08/01/2014

No. 12-51063
warrant-preparing process, we note the absence of precedent on holding
suspects and their “vehicle” in order to prepare a proper warrant request, as
opposed just to searching under exigent circumstances without a warrant. We
are addressing those issues for one of the first times in this circuit. It is clear
that detention cannot be prolonged just to investigate, but Agent Howard was
corroborating information already known by law enforcement in order to be the
affiant when requesting a search warrant. We earlier observed that Agent
Howard’s testimony was somewhat ambiguous, first asserting three things he
knew early on but then correcting some unstated part of that assertion.
Regardless, we “should uphold the district court’s ruling to deny the
suppression motion ‘if there is any reasonable view of the evidence to support
it.’” Michelletti, 13 F.3d at 841 (citation omitted). The ruling of the district
court, while determining Massi’s detention not to be unconstitutionally
prolonged, found in the alternative that the good faith exception would apply
“because there was a relatively large amount of persuasive evidence presented
to the magistrate judge, and Agent Howard subjectively believed he had acted
in accordance with the law.” We do not find that the ambiguity in Agent
Howard’s testimony prevents a reasonable view of the evidence that would
support the district court’s ruling as to the applicability of the good faith
exception.
When Agent Howard arrived at the airport, it was objectively reasonable
for an officer in his position to believe that no constitutional violation had yet
occurred, that probable cause for a search existed, and that he was justified in
taking the steps needed to confirm known facts, prepare an affidavit to present
to a magistrate, and obtain a search warrant. Our examination of caselaw
addressing unlawful detention does not clearly signal whether or how the
delays inherent in obtaining a warrant interact with unlawful seizures under
22

Case: 12-51063

Document: 00512719470

Page: 23

Date Filed: 08/01/2014

No. 12-51063
the Fourth Amendment. As McClain noted, “[s]ometimes the line between
good police work and a constitutional violation is fine indeed.” Id. at 563.
Complicating a reasonable officer’s objective awareness is our prior
observation that the “poisoned tree” of improper law enforcement did not cause
the discovery of the evidentiary “fruit” summarized in the affidavit. Massi’s
constitutional rights were violated when he was detained while the affidavit
was prepared and a search warrant issued, but the evidence relied upon by the
affidavit had been uncovered prior to then.
The prolonged detention was “close enough to the line of validity” that
an objectively reasonable officer preparing the affidavit for the warrant would
believe in the validity of the prior conduct.
B. Leon Exceptions to the Good Faith Exception
We next consider whether the search warrant executed by Agent Howard
was properly obtained and executed so as to be within the ambit of the good
faith exception.

In Leon, the Supreme Court identified four situations in

which the good faith exception to the warrant requirement does not apply:
(1) when the issuing magistrate was misled by information in an
affidavit that the affiant knew or reasonably should have known
was false; (2) when the issuing magistrate wholly abandoned his
judicial role; (3) when the warrant affidavit is so lacking in indicia
of probable cause as to render official belief in its existence
unreasonable; and (4) when the warrant is so facially deficient in
failing to particularize the place to be searched or the things to be
seized that executing officers cannot reasonably presume it to be
valid.
Woerner, 709 F.3d at 533-34 (citing Leon, 468 U.S. at 921-25). In determining
whether the good faith exception applies, “we do not attempt an ‘expedition
into the minds of police officers’ to determine their subjective belief regarding
the validity of the warrant.” United States v. Payne, 341 F.3d 393, 400 (5th
Cir. 2003) (quoting Leon, 468 U.S. at 922 n.23).
23

Rather, the analysis “is

Case: 12-51063

Document: 00512719470

Page: 24

Date Filed: 08/01/2014

No. 12-51063
confined to the objectively ascertainable question whether a reasonably well
trained officer would have known that the search was illegal despite the
magistrate’s authorization.” Id (quotation marks omitted).
Massi’s arguments about the good faith exception discuss only the third
and fourth Leon scenarios. We similarly limit our analysis but also address an
implicit argument that arises from the fruit of the poisonous tree doctrine.
1. The affidavit’s indicia of probable cause and the reasonableness
of official belief in the existence of probable cause
Massi states that the affidavit was merely “bare bones,” contained
conclusory statements, and lacked the richness of detail necessary for the
establishment of probable cause such that no reasonable officer could have
reasonably relied on it. He argues that the sole corroborated fact which was
brought to the attention of the warrant-issuing magistrate was the airplane’s
suspicious flight pattern.
The reasonableness of an officer’s reliance on a warrant is a question we
review de novo. United States v. Wylie, 919 F.2d 969, 974 (5th Cir. 1990).
“When a warrant is supported by more than a ‘bare bones’ affidavit, officers
may rely in good faith on the warrant’s validity.” United States v. Satterwhite,
980 F.2d 317, 321 (5th Cir. 1992). “‘Bare bones’ affidavits contain wholly
conclusory statements, which lack the facts and circumstances from which a
magistrate can independently determine probable cause.” Id.
In reviewing the affidavit, we agree with the district court’s assessment
that it contains “ample evidence” and find that its content was sufficient to
permit a reasonable officer to rely on the resulting warrant. Agent Howard
provided information based on his observations as well as those of other law
enforcement officers. He described the suspicious flight pattern; the resultant
ramp check and Massi’s response to a requested search; the prior conviction of
the airplane’s owner for cocaine trafficking and money laundering; Massi’s
24

Case: 12-51063

Document: 00512719470

Page: 25

Date Filed: 08/01/2014

No. 12-51063
travel to Tijuana, Mexico in the days prior to his boarding the airplane; the
existence of a cardboard box inside the airplane; and the contradictory
statements about the ownership of the box. Taken collectively, these facts are
far from a “bare bones” recitation of conclusory statements. Rather, they
represent an assemblage of facts discovered during the investigatory stop that
were corroborated by Agent Howard and were appropriately presented and
considered as probable cause to proceed with the process of obtaining a warrant
to search the airplane.
2. Facial deficiencies of the warrant and an executing officer’s
reasonable presumption of validity
Massi also argues the good faith exception is inapplicable under the
fourth Leon scenario, where a warrant fails “to particularize the place to be
searched or the things to be seized” and “the executing officers cannot
reasonably presume it to be valid.” Leon, 468 U.S. at 923. The warrant
specified that the 1990 Mooney M20J airplane with tail number N201SE was
to be searched for evidence of a crime, contraband, fruits of a crime, or other
items illegally possessed. Further, the warrant incorporated the facts in Agent
Howard’s affidavit and its discussion of the airplane, the cardboard box within
the airplane, and the facts that supported the probable cause finding that led
to the issuance of the warrant. The warrant was sufficient in its particularity
to permit an executing officer to presume it to be valid and thereby forecloses
Massi’s challenge to the warrant’s facial sufficiency.
3. The good faith exception and the fruit of the poisonous tree
doctrine under Leon
Our analysis of the good faith exception, first under McClain and then
under Leon, has separated those two lines of precedent. We find it equally
valid, and perhaps simpler in concept, to join the two, focusing on the first
element of Leon. We determine that this approach is consistent with both
25

Case: 12-51063

Document: 00512719470

Page: 26

Date Filed: 08/01/2014

No. 12-51063
cases, though we are chary to engraft anything onto settled Supreme Court
precedent.

Therefore, we undertake this final discussion as a means to

understand the interaction of the good faith exception to the exclusionary rule
and

a

warrant-executing

officer’s

knowledge

of

an

earlier-in-time

constitutional violation that would invalidate the search warrant.
Had Agent Howard knowingly hidden or misrepresented the course and
duration of the investigation at the airport to the magistrate judge, making
him unaware of a constitutional violation, such action could be seen as
equivalent to misleading the magistrate by falsities in the affidavit or
statements that are in reckless disregard of the truth under the first Leon
scenario. See Leon, 468 U.S. at 923. The first element of Leon focused on
omissions or falsities that distort the finding of probable cause; we are
suggesting that failure to acknowledge constitutional violations that led to the
discovery of the evidence in the affidavit could similarly lead to the
unavailability of the good faith exception under Leon.
We addressed a related argument in Woerner, considering whether an
infirmity in the warrant existed if “the magistrate’s probable cause finding is
based on evidence that was the product of an illegal search or seizure.” 709
F.3d at 534. That panel noted but did not hold that this issue could give rise
to a fifth scenario in which the good faith exception would be inappropriate.
Id. We conclude that the issue presented by Massi’s circumstances is more
easily considered under Leon by equating the misleading of the issuing
magistrate as to a possible constitutional violation through an omission with
the first Leon scenario, submission of an affidavit with affirmatively
misleading information.
Considered under this paradigm, Agent Howard properly explained the
timeline in his affidavit. He said that “at approximately [7:30 p.m. he] received
26

Case: 12-51063

Document: 00512719470

Page: 27

Date Filed: 08/01/2014

No. 12-51063
information about an airplane with suspicious flight patterns” that was parked
at Midland International Airport. He then recounted the events at the airport
prior to his arrival that involved MPD and Agents Knight and Garnett.
Though the specific time at which Massi’s encounter with law enforcement
began was not stated, it was clear from the affidavit that multiple interactions
between law enforcement and the suspects occurred prior to 7:30 p.m.
Additionally, the magistrate of course knew what time it was when he was
ruling on the application. We find nothing about the affidavit, through either
affirmative statement or omission, to have been misleading about the length
of Massi’s detention.
Agent Howard did not have the benefit of our judicial hindsight as he
worked to obtain and execute a search warrant. To suppress the evidence
derived from this warrant would not serve the interest of deterring future
constitutional violations.

See Leon, 468 U.S. at 919-20.

The good faith

exception to the exclusionary rule applies here where the search warrant,
though ultimately obtained as a result of an illegal detention in violation of the
Fourth Amendment, was obtained and executed by a law enforcement officer
in good faith and under an objectively reasonable belief that it was valid and
relied upon appropriately obtained evidence. Under the good faith exception,
the evidence obtained as a result of the execution of the search warrant was
properly admitted.
AFFIRMED.

27

Case: 12-51063

Document: 00512719470

Page: 28

Date Filed: 08/01/2014

GRAVES, Circuit Judge, dissenting.
After a ramp check at the Midland airport and a more-than-six-hour
detainment, during which time a canine failed to alert on any presence of
narcotics on either the airplane or luggage, officers obtained a search warrant
and found marijuana in a cardboard box behind the rear seat. The district
court denied Matthew Joseph Massi’s motion to suppress, finding that no
constitutional violation had occurred and, alternatively, that a good faith
exception to the exclusionary rule applies. The majority concludes that there
was a constitutional violation, but affirms the denial of the motion to suppress
by extending the good faith exception beyond that for which it was intended. I
disagree and would conclude that the evidence should be suppressed because
the duration and circumstances of Massi’s prolonged detention transformed
into a de facto arrest without probable cause. Further, I would conclude that
the good faith exception is not applicable. Because I would reverse the district
court’s denial of Massi’s motion to suppress, I respectfully dissent.
Massi asserts that he was illegally detained at the airport and that his
detainment was unconstitutionally prolonged without probable cause. He does
not argue that the ramp check itself was illegal, but asserts that he and the
pilot should have been free to leave as soon as authorities checked the
documents.

He further asserts that his “prolonged seizure” exceeded the

parameters of an investigative stop, resulting in an illegal arrest. Therefore,
Massi asserts that all of the evidence seized by the authorities pursuant to the
warrant should have been suppressed as the fruit of the poisonous tree.
The Government asserts that Massi was validly detained for a ramp
check and a Terry stop, and that the detention did not become an arrest until
a search warrant was issued and contraband was found. Alternatively, the
28

Case: 12-51063

Document: 00512719470

Page: 29

Date Filed: 08/01/2014

No. 12-51063
Government asserts that the evidence obtained pursuant to the search would
still be admissible under the good faith exception to the exclusionary rule.
The majority concludes that sufficient reasonable suspicion existed to
justify an investigatory stop under Terry v. Ohio, 392 U.S. 1 (1968), which
allowed the investigation to continue beyond the ramp check. Specifically, the
majority says that:
[T]he obligation to submit to a ramp check allowed the airplane
and Massi to be held at the airport initially. The law enforcement
officers then had a proper basis to continue the encounter beyond
the regulatory ramp check under the reasonable suspicion
standard in Terry, even if the facts giving rise to suspicion were
known prior to law enforcement contact with Massi.
I agree that there was sufficient reasonable suspicion to justify a Terry
stop, but I disagree with this statement because there was no justification for
the stop to continue beyond the initial ramp check and investigatory stop. I
also disagree with any suggestion that facts known prior to law enforcement
contact with a defendant not only allow a Terry stop, but also provide a basis
for the stop to continue.
Investigative detention must last “no longer than required to effect the
purpose of the stop.” United States v. Jenson, 462 F.3d 399, 404 (5th Cir. 2006).
“Once the purpose of a valid [Terry] stop has been completed and an officer’s
initial suspicions have been verified or dispelled, the detention must end unless
there is additional reasonable suspicion supported by articulable facts.”
United States v. Estrada, 459 F.3d 627, 631 (5th Cir. 2006) (emphasis added);
United States v. Machuca-Barrera, 261 F.3d 425, 432 n.21 (5th Cir. 2001)
(stating that questioning unrelated to the justification for a stop that extends
the stop’s duration violates the Fourth Amendment). Articulable suspicion
means more than a hunch. Terry, 392 U.S. at 21-22. This court has considered
Terry principles in the ramp check context. See, e.g., United States v. Zukas,
29

Case: 12-51063

Document: 00512719470

Page: 30

Date Filed: 08/01/2014

No. 12-51063
843 F.2d 179, 181-83 (5th Cir. 1988). An arrest has occurred if, “in view of all
the circumstances surrounding the incident, a reasonable person would have
believed that he was not free to leave.” United States v. Mendenhall, 446 U.S.
544, 554 (1980). A person is seized when, “by means of physical force or a show
of authority, his freedom of movement is restrained.” Id. at 553. Even short
of an arrest, a person’s “liberty interest in proceeding with his itinerary” may
be “effectively restrain[ed]” if his personalty is detained for investigation.
United States v. Place, 462 U.S. 696, 708 (1983).
In this situation, the ramp check and the Terry stop coincided. The
majority concedes that the reasonable suspicion came from information
received from the Air Marine Operations Center (AMOC). This was prior to
and the basis for the ramp check, which was the investigatory stop. Upon the
completion of the ramp check/Terry stop, there was no additional reasonable
suspicion to justify the extension of the stop. See United States v. Brigham,
382 F.3d 500, 506-07 (5th Cir. 2004) (emphasis added). At that point, the
detention should have ended. See Estrada, 459 F.3d at 631. The paperwork
was in order and the authorities had no articulable suspicion of any illegal
activity. But Massi and the pilot were already being detained and were not
free to leave. The authorities then asked for and were denied consent to search
and the canine failed to alert, further indicating that any suspicions had been
dispelled. 1 That is the second point at which the detention should have ended.
There is nothing in the record to establish the existence of any evidence
of criminal activity.

There is also nothing in the record to indicate that

1I

note that, while Massi did attempt to close the door of the airplane after denying consent
to search, the door was actually closed by a law enforcement officer. The majority also refers to
“Massi’s inconsistent statements as to his knowledge and ownership of the box.” Actually, Howard’s
affidavit states, and testimony supports, that Agent Knight asked Massi who the box belonged to
and he responded: “I don’t know what you are talking about.” Knight asked Massi again and Massi
said: “I don’t know of any boxes.” Knight then clarified that the reference was to the box the pilot
saw him put in the plane and Massi admitted “[t]he box is mine.”

30

Case: 12-51063

Document: 00512719470

Page: 31

Date Filed: 08/01/2014

No. 12-51063
authorities had anything more than a hunch that the men were involved in
criminal activity. A hunch does not create articulable suspicion. Terry, 392
U.S. at 21-22. There is nothing in the record to indicate that authorities asked
the men about the flight activity, which authorities later deemed “suspicious,”
why they spent only 12 hours in Las Vegas, or about the purpose of Massi’s
recent visit to Tijuana. Although Tijuana may be “a known center of drug
activity,” obviously, it is not illegal to visit Tijuana.

The record further

indicates that evidence of “suspicious” flight activity was not conveyed by
AMOC to authorities until after the ramp check and investigatory stop had
been completed.
Immigration

and

Agent Josh Howard, criminal investigator for U.S.
Customs

Enforcement

(ICE),

Homeland

Security

Investigations (HSI), testified that AMOC initially requested a ramp check and
informed Midland Police that the registered owner of the aircraft had a prior
narcotics-related conviction.

With regard to the flight activity, Howard

testified: “Honestly, I don’t recall if they told me exactly what was going on at
the time, but I did – I did corroborate the information.” Howard also testified
that much of his corroboration was done when he was back at his office writing
the search warrant affidavit several hours later.
Notwithstanding the likelihood of the stop turning into a de facto arrest
at an earlier point in time, the majority ultimately concludes that Massi’s
investigatory stop turned into a de facto arrest without probable cause at some
point after Howard’s arrival on the scene. See United States v. Zavala, 541
F.3d 562, 574 (5th Cir. 2008). In analyzing probable cause for an arrest, the
majority states that the “facts and circumstances known to law enforcement
by the time of Agent Howard’s 7:30 p.m. arrival were all that was known until
the midnight search of the plane.” But, as set out above, the record indicates
that some of that information was likely obtained after Howard arrived and
31

Case: 12-51063

Document: 00512719470

Page: 32

Date Filed: 08/01/2014

No. 12-51063
after he returned to his office. Nevertheless, the majority concludes that until
the midnight search, the officers only had suspicions and not probable cause
for an arrest.

However, after concluding that Massi was subjected to an

unconstitutional arrest at the airport, the majority then opines that the
evidence obtained pursuant to that unconstitutional arrest should not be
suppressed as the fruit of the poisonous tree under the good faith exception.
As stated by the majority, the good faith exception provides that
“evidence obtained during the execution of a warrant later determined to be
deficient is nonetheless admissible if the executing officer’s reliance on the
warrant was objectively reasonable and made in good faith.” United States v.
Woerner, 709 F.3d 527, 533 (5th Cir. 2013). The exception involves a judicial
determination that exclusion of the evidence does not advance the interest of
deterring unlawful police conduct. United States v. Leon, 468 U.S. 897 (1994).
The good faith exception limits exclusion where “the marginal or nonexistent
benefits produced by suppressing evidence obtained in objectively reasonable
reliance on a subsequently invalidated search warrant cannot justify the
substantial costs of exclusion.” Leon, 468 U.S. at 922. The good faith exception
does not apply:
(1) when the issuing magistrate was misled by information in an
affidavit that the affiant knew or reasonably should have known
was false; (2) when the issuing magistrate wholly abandoned his
judicial role; (3) when the warrant affidavit is so lacking in indicia
of probable cause as to render official belief in its existence
unreasonable; and (4) when the warrant is so facially deficient in
failing to particularize the place to be searched or the things to be
seized that executing officers cannot reasonably presume it to be
valid.
Woerner, 709 F.3d at 534 (citing Leon, 468 U.S. at 923).
The majority characterizes the question here as whether the exception
permits the admissibility of evidence over a “possible taint” caused by the
32

Case: 12-51063

Document: 00512719470

Page: 33

Date Filed: 08/01/2014

No. 12-51063
Fourth Amendment violation that would otherwise be excluded as fruit of the
poisonous tree. The majority indicates that it says “‘possible taint’ because
there is not a clear causal connection between the unconstitutional detention
and the acquisition of evidence used to support the search warrant.” But
clearly there is a causal connection between the unconstitutional detention and
the evidence obtained in the search since officers would not have been able to
conduct the search absent the unconstitutional detention. The authorities not
only detained Massi and the pilot, but also their documents, luggage, and
airplane. Further, as stated above, there is evidence that all of the information
used in the warrant was not acquired prior to the detention, as the majority
concedes.
The majority acknowledges that Woerner is factually distinguishable,
but says that it “signals an openness to applying the good faith exception where
an earlier-in-time constitutional violation exists alongside a search warrant
that was sought and executed in good faith.” Woerner involved two separate
investigations of online activity by two separate agencies and two separate
search warrants. As the majority acknowledges, “[b]oth the interrogation and
unlawful search were undertaken by a different law enforcement entity than
that of the officers who pursued the search warrant at issue; the two
investigations were parallel and the officers seeking the search warrant did
not know of the other. The majority says that, in Woerner, this court concluded
that suppression was not justified and that the good faith exception applied.
While that statement is not inaccurate, a more fulsome discussion of Woerner
is warranted.
On July 12, 2010, the Los Fresnos Police Department (LFPD) executed
an expired search warrant on Woerner’s residence and seized evidence of
possession of child pornography. The warrant came as a result of a profile
33

Case: 12-51063

Document: 00512719470

Page: 34

Date Filed: 08/01/2014

No. 12-51063
Woerner had posted on the file-sharing network Gigatribe and files he had
shared with a detective in Illinois on April 14, 2010. That detective traced the
Internet Protocol (IP) address and reported the matter to LFPD. During the
same time period, the Federal Bureau of Investigation (FBI) was conducting a
separate, unknown undercover operation on Gigatribe and accessed child
pornography from the same IP address on May 14, 2010. As a result, the FBI
applied for and received a search warrant for Woerner’s residence. On July 13,
2010, FBI agents were preparing to execute this warrant when LFPD informed
them of the earlier search and arrest. The FBI proceeded with the search and
seized film, videos, tapes, and magazines.

The following day, the FBI

interrogated Woerner and subsequently took over the investigation, which
involved subsequent searches, including a search of an email account (the
fantastikaktion account).
Prior to trial, Woerner moved to suppress evidence. The district court
found, in part, that the good faith exception did not apply and suppressed all
of the evidence seized from Woerner’s home by the LFPD pursuant to an
expired search warrant and the subsequent statements that he made to the
FBI in the parallel investigation on the grounds that the “evidence was seized
pursuant to, and his statements were tainted by, the unlawful July 12 search
of his home.” Woerner, 709 at 533. However, the district court did not suppress
evidence derived from the FBI’s interview of a victim and his family or later
search of Woerner’s residence or fantastikaktion account, concluding that the
evidence fell within the good faith exception to the exclusionary rule. Id.
Woerner appealed, arguing, in part, that the emails from the
fantastikaktion account should have been suppressed because the later
warrant was supported by evidence obtained through the earlier unlawful
search. This court affirmed the district court’s application of the good faith
34

Case: 12-51063

Document: 00512719470

Page: 35

Date Filed: 08/01/2014

No. 12-51063
exception in denying the suppression of only this later evidence obtained
through a later warrant based, in part, on statements Woerner had made
during the custodial interrogation linking his possession of child pornography
to the fantastikaktion account. In doing so, this court said:
We decline to announce a categorical rule governing this situation,
following Leon’s guidance that “suppression of evidence obtained
pursuant to a warrant should be ordered only on a case-by-case
basis and only in those unusual cases in which exclusion will
further the purposes of the exclusionary rule.” . . . We note that
the purpose of the exclusionary rule – deterring future Fourth
Amendment violations – would be served, in some cases, by
suppressing evidence seized pursuant to a warrant supported by
evidence obtained through an unlawful search. . . . For example,
if the officer applying for the warrant knew or had reason to know
that the information was tainted and included it anyway without
full disclosure and explanation, then suppressing the evidence
seized pursuant to that warrant “pay[s] its way by deterring
official lawlessness.”
Woerner, 709 F.3d at 534. (Internal citations omitted).
Based on Woerner, the evidence here should clearly be suppressed.
Howard and his agency were involved in this investigation the entire time and
he knew exactly what had occurred. This is akin to the first warrant in
Woerner in which the evidence was suppressed and the good faith exception
did not apply. As established previously herein, Howard’s reliance on the
warrant was not objectively reasonable or made in good faith.

Howard’s

affidavit to the warrant was misleading in that it fails to disclose that the
investigation began at approximately 6 p.m. and Massi had been detained for
more than an hour prior to 7:30 p.m., which is the time Howard states that he
received initial information. Howard testified during the suppression hearing
that Midland Police were contacted at 6 p.m. and his agency was brought into
the investigation at approximately 6:20 p.m. Although Howard did not arrive
35

Case: 12-51063

Document: 00512719470

Page: 36

Date Filed: 08/01/2014

No. 12-51063
on the scene until approximately 7:30 p.m. because he had been at a personal
function, other agents were already on the scene and Howard had already
spoken to another agent and AMOC prior to his arrival.

Not only does

Howard’s affidavit for the warrant not contain relevant information regarding
the time period of the investigation or of the unconstitutional arrest, but it also
fails to state what information was actually known prior to the investigatory
stop or what information was obtained after the unconstitutional arrest had
already occurred. Because he knew what had occurred, Howard could not rely
in good faith on the warrant’s validity.
Further, even with the omissions and misleading information, the
warrant is lacking in indicia of probable cause and fails to particularize the
things to be searched. The affidavit contains generalized statements regarding
drug trafficking and the common practices of traffickers, and a general list of
items to be seized, i.e., “all evidence, fruits and instrumentalities pertaining to
violations of Title 21 United States Code, Sections 841. . . .” There is very
little specific information in the affidavit other than things such as: some of
the flight information; the denial of consent to search; the observation of a
“cardboard box approximately 18 to 24 inches across” behind the rear seat and
the discussion regarding the box; that Massi crossed from Tijuana three days
before; 2 that the registered owner of the aircraft is Vernon Tynes and that he
had a cocaine trafficking offense in 1992; and conclusory statements, such as
“[t]his flight requires approximately 6 refuelings.”
The majority concedes that an “unconstitutional seizure” occurred. As a
direct result of that constitutional violation, authorities obtained a search
warrant and tainted evidence.

Exclusion of that tainted evidence would

I note that the affidavit states that “[q]ueries of government databases revealed Massi
crossed from Tijuana, Baha California, Mexico to San Ysidro on May 13, 2012.”
2

36

Case: 12-51063

Document: 00512719470

Page: 37

Date Filed: 08/01/2014

No. 12-51063
certainly advance the interest of deterring unlawful police conduct in the form
of detaining a person for more than six hours without probable cause in an
attempt to pursue an investigation to develop probable cause. Because the
benefits produced by suppressing the evidence here are not merely marginal
or nonexistent and do justify the costs of exclusion, the good faith exception
does not apply. Leon, 468 U.S. at 922.
Notwithstanding that I would find that the good faith exception does not
apply under Woerner and Leon, I will address the other cases cited by the
majority from the Sixth, Second and Eight Circuits. What is clear, as the
majority acknowledges, is that these other circuits have only applied the
exception in limited circumstances, none of which exist here.
The majority finds United States v. McClain, 444 F.3d 556 (6th Cir.
2005), to be most persuasive. But a careful examination of the facts in McClain
undermines its persuasiveness. The initial entry into the house based on the
erroneous belief by the police of possible criminal activity did not uncover any
marijuana plants.

In the initial entry, officers discovered inward-facing

reflective paper on the windows in the basement, a large amount of electrical
wiring connected to a junction box, what appeared to be plant stimulators, and
some boxes marked “grow lights.” Officers did not see any marijuana in the
house, but concluded that a grow house was being set up. McClain, 444 F.3d
at 560. Following the entry, officers informed their supervisor, who contacted
Officer Brian Murphy of the Sumner County Drug Task Force. Murphy then
began an investigation that lasted approximately six weeks and involved
surveillance of the house and several other properties. Murphy eventually
obtained warrants to search the house and five other properties. The warrant
affidavit relied in part on evidence obtained during the initial warrantless
search. During that search, authorities recovered 348 marijuana plants and
37

Case: 12-51063

Document: 00512719470

Page: 38

Date Filed: 08/01/2014

No. 12-51063
growing equipment from the house.

Id.

The district court granted the

defendants’ motions to suppress, finding that the warrantless entry and search
of the house violated the Fourth Amendment and that the good faith exception
of the exclusionary rule did not apply. The government appealed, and the Sixth
Circuit reversed.
The question before the Sixth Circuit was whether the good faith
exception can apply in a situation in which the affidavit for the warrant is
tainted by evidence obtained in violation of the Fourth Amendment. The court
concluded that McClain was “one of those unique cases in which the Leon good
faith exception should apply despite an earlier Fourth Amendment violation.”
McClain, 444 F.3d at 565. The court relied on United States v. White, 890 F.2d
1413, 1419 (8th Cir. 1989), for the proposition that “the facts surrounding the
initial Fourth Amendment violation were ‘close enough to the line of validity
to make the officer’s belief in the validity of the warrant objectively
reasonable.’” McClain, 444 F.3d at 566. Specifically, the court said:
[W]e do not believe that the officers were objectively unreasonable
in suspecting that criminal activity was occurring inside McClain’s
home, and we find no evidence that the officers knew they were
violating the Fourth Amendment by performing a protective sweep
of the home. More importantly, the officers who sought and
executed the search warrants were not the same officers who
performed the initial warrantless search, and Officer Murphy’s
warrant affidavit fully disclosed to a neutral and detached
magistrate the circumstances surrounding the initial warrantless
search.
Id. (Emphasis added). The court then found that:
Because the officers who sought and executed the search warrants
acted with good faith, and because the facts surrounding the initial
warrantless search were close enough to the line of validity to make
the executing officers’ belief in the validity of the search warrants
objectively reasonable, we conclude that despite the Fourth
38

Case: 12-51063

Document: 00512719470

Page: 39

Date Filed: 08/01/2014

No. 12-51063
Amendment violation, the Leon exception bars application of the
exclusionary rule in this case.
Id. (Emphasis added).
Based on McClain, the majority adopts the reasoning that two
requirements must be met for the good faith exception to apply to evidence
obtained as the result of the execution of a search warrant. The requirements
adopted by the majority are:
(1) the prior law enforcement conduct that uncovered evidence
used in the affidavit for the warrant must be “close enough to the
line of validity” that an objectively reasonable officer preparing the
affidavit or executing the warrant would believe that the
information supporting the warrant was not tainted by
unconstitutional conduct, and (2) the resulting search warrant
must have been sought and executed by a law enforcement officer
in good faith as prescribed by Leon.
However, as set out above, that is not exactly what the Sixth Circuit said.
Also, one glaring omission in the majority’s newly-adopted reasoning involves
the “more” important factor that the Sixth Circuit considered and I quoted
above that, “the officers who sought and executed the search warrants were
not the same officers who performed the initial warrantless search.” McClain,
444 F.3d at 566. Despite that, the majority sees no basis for including this one
requirement found to be of significant importance by the other circuits it cites.
Instead, the majority says that, “[i]t is not awareness of the existence of the
conduct that later is found to be improper that is important, but it is awareness
at the time of presenting the affidavit that the conduct violated constitutional
rights that would affect the application of the good-faith exception.” Yet, the
majority fails to reconcile that statement with its own finding that the prior
police conduct was unconstitutional.

39

Case: 12-51063

Document: 00512719470

Page: 40

Date Filed: 08/01/2014

No. 12-51063
In this case, the officer who sought and executed the search warrant also
participated in the unconstitutional arrest. Detaining someone for hours until
it turns into a de facto arrest without probable cause is not close enough to the
line of validity to make any possible belief Howard had in the validity of the
search warrant objectively reasonable.

The majority dismisses Howard’s

statements indicating he did not learn some necessary facts until after the
unconstitutional arrest and cites United States v. Michelletti, 13 F.3d 838 (5th
Cir. 1994) as support.

However, the portion of Michelletti quoted by the

majority addresses the general standard for upholding the district court’s
ruling to deny a motion to suppress. Id. at 841. Here, the majority has already
held that the district court erred in finding the unconstitutional detention to
be constitutional and is merely determining the application of a good faith
exception. Michelletti provides no authority for the application of a good faith
exception.
The majority cites the Eighth Circuit case of United States v. Fletcher,
91 F.3d 48, 51-52 (8th Cir. 1996), for the proposition that the Leon exception
was applicable to a subsequent warrant-authorized search of luggage despite
the initial Fourth Amendment violation. In that case, upon his arrival at his
destination, Fletcher’s bag was delayed by the airline because of his last
minute ticket purchase. Fletcher left the airport and returned at a later time
to retrieve his bag. For various reasons, officers grew suspicious of Fletcher
upon his initial arrival and began an investigation. Upon Fletcher’s return to
the airport to retrieve his bag, officers approached him and began a
conversation, during which Fletcher gave some contradictory statements.
Officers asked Fletcher for permission to search his bag. Fletcher consented
and then withdrew the consent. Officers then told Fletcher he was free to leave
but that his bag would be detained for a dog sniff. The dog was brought in and
40

Case: 12-51063

Document: 00512719470

Page: 41

Date Filed: 08/01/2014

No. 12-51063
alerted on the bag.

Officers then obtained a search warrant and

methamphetamine was discovered in the bag. The district court held that the
officers did not have reasonable articulable suspicion of criminal activity and
that the detention violated the Fourth Amendment, but suppression was not
warranted because the facts were “close enough to the line of validity to make
the officers’ belief in the validity of the detention and the validity of the search
warrant objectively reasonable.” Fletcher, 91 F.3d at 50. Though factually
distinguishable, a key point the Eighth Circuit made was that “officers
collected information to corroborate their suspicions before approaching
Fletcher by conducting additional surveillance and checking police records.”
Id. at 52. (Emphasis added).
Here, officers did not corroborate their suspicions or check police records
before approaching Massi. Instead, officers corroborated their suspicions after
they illegally detained Massi. The process of “corroborating” information is
typically part of the investigative process. Further, officers did not conduct
any additional surveillance.
The majority also cites United States v. Thomas, 757 F.2d 1359, 1368 (2d
Cir. 1985), for the Second Circuit’s finding that Leon was applicable to a search
of an apartment where the affidavit in support of the warrant contained
evidence in violation of the Fourth Amendment. Again, this case is factually
distinguishable as it involved a canine sniff outside a defendant’s apartment
that indicated the presence of narcotics and was used as probable cause to
obtain a search warrant. The search was part of an investigation that spanned
a period of nine years and involved nine undercover investigations. In any
event, the Second Circuit found that, because the magistrate concluded that
the canine sniff could form the basis for probable cause to search the
apartment, there was nothing more the officer could have or should have done
41

Case: 12-51063

Document: 00512719470

Page: 42

Date Filed: 08/01/2014

No. 12-51063
to insure that his search would be legal. Thus the good faith exception applied.
Specifically, the court said: “The magistrate, whose duty it is to interpret the
law, determined that the canine sniff could form the basis for probable cause;
it was reasonable for the officer to rely on this determination.” Thomas¸ 757
F.2d at 1368. That is clearly distinguishable from this case.
Further, there are Second, Eighth, Ninth and Eleventh Circuit cases
that have held that the good faith exception does not apply where a search
warrant was issued on the basis of tainted evidence. See United States v.
Reilly, 76 F.3d 1271, 1281-82 (2d Cir. 1996) (holding Leon inapplicable where
officers failed to disclose in warrant affidavit the circumstances involved in a
pre-warrant search; “Good faith is not a magic lamp for police officers to rub
whenever they find themselves in trouble.”); United States v. O’Neal, 17 F.3d
239, 243 n.6 (8th Cir. 1994) (issuance of search warrant could not sanitize prior
illegal conduct in obtaining supporting evidence as it would not be a deterrent);
United States v. McGough, 412 F.3d 1232, 1239-40 (11th Cir. 2005) (good faith
exception does not apply where a search warrant is issued on the basis of
evidence obtained as the result of an illegal search); and United States v. Vasey,
834 F.2d 782, 789-90 (9th Cir. 1987) (magistrate’s issuance of warrant based on
tainted evidence does not sanitize the taint).
The majority admits that Massi’s constitutional rights were violated
when he was detained while the affidavit was prepared and search warrant
issued, but says, in effect, that the prolonged detention by Howard was close
enough to the line of validity that Howard would believe in the validity of the
illegal detention. I disagree.
For the reasons stated herein, I would hold that the good faith exception
does not apply. Because I would reverse the district court’s denial of Massi’s
motion to suppress, I respectfully dissent.
42