US v. Ortiz-Vega

Filing

OPINION issued by Juan R. Torruella, Appellate Judge; Rogeriee Thompson, Appellate Judge and William J. Kayatta , Jr., Appellate Judge. Published. [14-1693]

Case: 14-1693

Document: 00117169618

Page: 1

Date Filed: 06/21/2017

Entry ID: 6101151

United States Court of Appeals
For the First Circuit
No. 14-1693
UNITED STATES OF AMERICA,
Appellee,
v.
ANGEL ORTIZ-VEGA,
Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Daniel R. Domínguez, U.S. District Judge]

Before
Torruella, Thompson, and Kayatta,
Circuit Judges.

Rafael F. Castro Lang for appellant.
Nelson Pérez-Sosa, Assistant United States Attorney, with
whom Rosa Emilia Rodríguez-Vélez, United States Attorney and
Mariana E. Bauzá-Almonte, Assistant United States Attorney, Chief,
Appellate Division, were on brief for appellee.

June 21, 2017

Case: 14-1693

Document: 00117169618

Page: 2

Date Filed: 06/21/2017

THOMPSON, Circuit Judge.

Entry ID: 6101151

Appellant Angel Ortiz-Vega

("Ortiz") was charged with several counts related to a drug
distribution conspiracy in Puerto Rico.

Ortiz was originally

represented by court-appointed counsel, Francisco M. Dolz-Sanchez
("Dolz"), but after seven months retained private counsel, Luis R.
Rivera-Rodriguez ("Rivera"), because, according to Ortiz, Dolz
failed

to

provide

throughout

plea

him

with

effective

negotiations.

Ortiz

assistance
raised

his

of

counsel

ineffective

assistance claim at several points prior to sentencing, claiming
that Dolz's lack of adequate communication cost him a better plea
deal.

The district court declined to rule on Ortiz's ineffective

assistance claim prior to sentencing, finding the motion to be
"premature."

Ortiz eventually pled guilty to a higher plea offer

negotiated by his new counsel and was sentenced in accordance with
that agreement.
On appeal, Ortiz argues, inter alia, that the district
court erred by refusing to rule on the merits of his ineffective
assistance claim prior to sentencing.

For the reasons discussed

below, we agree with Ortiz and remand the case to the district
court for further proceedings.
Background
In the summer of 2011, Ortiz was charged in a nine-count
superseding

indictment

along

with

over

a

hundred

other

co-

defendants allegedly involved in a large-scale drug conspiracy.

- 2 -

Case: 14-1693

Document: 00117169618

Page: 3

Date Filed: 06/21/2017

Entry ID: 6101151

For his role, Ortiz was charged with conspiracy to possess with
intent

to

distribute

various

controlled

substances

including

heroin, cocaine, marijuana, Percocet, and Xanax, as well as the
actual possession of those substances with intent to distribute
them,

within a thousand feet of a public school in violation of

21 U.S.C. §§ 841, 846, and 860 (Counts I-IV).

Ortiz was also

charged with aiding and abetting others in the use or possession
of firearms during the drug offenses in violation of 18 U.S.C.
§ 924(c) and 2 (Count V).
On August 6, 2012, Ortiz ultimately entered into a nonbinding plea agreement with the government, pursuant to Federal
Rule of Criminal Procedure 11(c)(1)(B), in which he agreed to plead
guilty to the conspiracy and firearms charges (Counts I and V)
with

an

applicable

United

States

Sentencing

Guidelines

("Guidelines") range of 168-180 months on both counts.
States

v.

Torres-Oliveras,

583

F.3d

37,

41

(1st

See United
Cir.

2009)

(discussing the difference between non-binding Type B and binding
Type C plea agreements).

The journey to reach this point of

agreement had proven long and contentious, with Ortiz switching
counsel and his previous (court-appointed) counsel, his current
(privately-retained)

counsel,

and

the

government

each

making

conflicting assertions as to the facts surrounding Ortiz's plea
negotiations.

We

necessarily

discuss

the

facts

surrounding

Ortiz's plea negotiations, since they form the basis of his present

- 3 -

Case: 14-1693

Document: 00117169618

Page: 4

Date Filed: 06/21/2017

Entry ID: 6101151

appeal and assertion that the district court erred in failing to
rule on his ineffective assistance claim prior to sentencing.
1. Plea Negotiations
Ortiz was arrested on the drugs and firearm charges
described above in late June 2011.
appointed as his attorney.

At that time, Dolz was

Dolz asserts that he first met with

Ortiz in July 2011 to discuss the charges lodged against Ortiz and
to conduct a full client interview.

On January 24, 2012, six

months after his arrest, Ortiz filed a pro se "Motion for Lawyer
Dismissal" in which he requested that Dolz be "released from his
position on [sic] [Ortiz's] case" because, according to Ortiz,
Dolz

had

"acted

in

a

[sic]

unreasonable

way"

communicated with him since he had been imprisoned.

and

had

not

The court did

not respond to Ortiz's pro se motion until six months after it was
filed (after Ortiz had replaced Dolz with a privately-retained
attorney), and the court ultimately dismissed Ortiz's pro se motion
as moot given his retention of new counsel.

The parties dispute

how often Dolz communicated with Ortiz and the substance of their
communications during plea negotiations.
According to Dolz, after Ortiz filed his pro se motion,
Dolz reached out to the government via email to discuss a possible
plea offer.1

Dolz asserts that he then visited Ortiz on March 6,

1

Dolz also states that there was an initial "verbal" plea
offer that no one took seriously. Dolz claims that the government
- 4 -

Case: 14-1693

Document: 00117169618

Page: 5

Date Filed: 06/21/2017

Entry ID: 6101151

2012 -- some eight months after first interviewing Ortiz -- to
further discuss Ortiz's case.

Dolz claims that at this meeting

Ortiz stated that he would only accept a plea offer of eighty-four
months (or seven years) for both counts.
On March 19, 2012, the government offered Ortiz a plea
deal well above seven years, with a Guidelines range of 130-147
months (or between a little over ten and a little over twelve
years) on both counts.
April

7,

2012

to

Dolz claims that he visited Ortiz again on

communicate

the

130-147

month

plea

offer.

According to Dolz, he advised Ortiz to take the offer, but Ortiz
rejected it and reiterated that he would only accept a plea deal
of seven years on both counts, or that he would go to trial.

Dolz

claims that as soon as he exited the prison after meeting with
Ortiz, Ortiz's wife called and informed him that Ortiz no longer
wanted to present a counteroffer of seven years to the government
as they had just discussed, but instead wanted to present a
counteroffer of sixty months on the conspiracy charge (Count I)
and

wanted

the

firearms

charge

(Count

V)

to

be

dismissed

altogether.

had initially offered Otiz a verbal plea deal for 240 months
sometime in August or September of 2011.
Dolz claimed that
although the government had tendered this verbal offer, neither of
them took the offer seriously. Dolz states that he informed Ortiz
of this verbal offer, but the record does not specify when Dolz
communicated this offer or Ortiz's response to it.

- 5 -

Case: 14-1693

Document: 00117169618

Accordingly,

on

Page: 6

April

Date Filed: 06/21/2017

12,

2012,

Dolz

government Ortiz's counteroffer of sixty months.

emailed

the

The government

responded to Dolz's email with a one-liner: "Rejected.
trial then?"

Entry ID: 6101151

See you in

The record is ambiguous as to whether Dolz ever

responded to this rejection of Ortiz's counteroffer, but it does
indicate that Dolz may not have communicated with Ortiz again
regarding plea negotiations until after Ortiz had retained new
counsel three months later in July 2012.
Dolz asserts that at some point after Rivera had been
retained (on July 24, 2012), but presumably prior to Dolz's last
meeting with Ortiz on the following day (July 25, 2012), he
communicated with the government via email to see if the 130-147
month

offer

was

still

on

the

table.

Dolz

claims

that

the

government informed him that the original offer had expired and
that the new offer was 180 months, which the government had also
communicated to Rivera.

Dolz also indicated that the government

was mistaken in its statement that the original offer had expired
and claimed that he believed that the original offer of 130-147
months had not expired and would not expire until July 31, 2012 - the date set by the court for any change of plea.
On

July

25,

2012,

the

day

after

Rivera

filed

his

appearance in the case, Dolz claims that he visited and informed
Ortiz that "there was a plea offer outstanding and that July 31,
2012 was the deadline for the [change of plea] motion."

- 6 -

It is

Case: 14-1693

Document: 00117169618

Page: 7

Date Filed: 06/21/2017

Entry ID: 6101151

unclear from the record whether the "outstanding plea offer"
referenced by Dolz was the new 180 month offer or the previous
130-147

month

offer

which

Dolz

expiration date of July 31, 2012.2
final

July

meeting,

he

apparently

believed

had

an

Dolz also asserts that at this

informed

Ortiz

that

his

previous

counteroffer of sixty months had been rejected and that there was
nothing else Dolz could do since Ortiz had retained Rivera to
handle his case.

Despite Ortiz retaining new counsel, Dolz

contends that the government continued to communicate with him
concerning Ortiz's case and that on July 31, 2012 the government
sent him a new plea offer of 168-180 months that was slated to
expire on August 1, 2012.
The government mostly agrees with Dolz's account of plea
negotiations,

but

also

states

that

after

rejecting

Ortiz's

counteroffer of sixty months, it understood that the original 130147 month offer had been rescinded.

2

It is unclear at what point Dolz was made aware of the 180
month offer and if he communicated that offer to Ortiz. On the
one hand, Dolz claims that the government informed him that the
130-147 month plea offer had expired and that the new plea offer
was 180 months prior to his meeting with Ortiz on July 25, 2012.
On the other hand, Dolz claims that he was unaware of the new 168180 month offer until July 31, 2012 when the government emailed
him a new plea agreement. Dolz also indicated that he believed
that it was Rivera who permitted the original 130-147 month offer
to expire because Dolz believed that the original offer did not
expire until July 31, 2012 -- after Rivera had been retained. It
is therefore also unclear what "outstanding offer" Dolz
communicated to Ortiz on his visit on July 25, 2012 (180 months or
130-147 months).

- 7 -

Case: 14-1693

Document: 00117169618

Page: 8

Date Filed: 06/21/2017

Entry ID: 6101151

As expected Ortiz has a very different view of what
occurred during plea negotiations.

According to Ortiz, Dolz only

visited him twice: once on April 7, 2012 to communicate the
original 130-147 month plea offer and again after Ortiz had
retained Rivera as his new counsel.3

Ortiz claims that Dolz failed

to keep him updated concerning plea negotiations and failed to
communicate

with

counteroffer.

him

after

the

government

rejected

his

In response to Ortiz's assertions, at a hearing

before the district court, Dolz said that he "saw [Ortiz] as [he]
need[ed] to see him" and that Ortiz was given the information
needed regarding his case despite his assertion that Dolz only
visited him twice.

At another hearing, Ortiz countered that he

never communicated to Dolz that he would rather go to trial, and
that he always wanted to plead guilty, but that he was looking for
the best deal.

Of course, Dolz denied these contentions.

2. Plea Agreement
Regardless of the back and forth alleged by Ortiz and
Dolz concerning plea negotiations, Ortiz did finally enter into a
plea agreement with the government that was negotiated by his new
counsel Rivera.

According to Rivera, by the time he got involved

3

Ortiz cites the jail visitation log record to support his
claim that Dolz only visited him twice.
According to those
records, Dolz visited Ortiz on April 7, 2012 and again after Rivera
had been retained. As discussed above, Dolz argues that he did
not always sign the visitation log when he visited Ortiz and that
there were more than two visits that had not been recorded.

- 8 -

Case: 14-1693

Document: 00117169618

Page: 9

Date Filed: 06/21/2017

Entry ID: 6101151

with the case, the government refused to offer Ortiz the original
plea offer of 130-147 months, claiming that its initial offer had
expired.

Ortiz alleges that he was faced with the choice of a

higher plea deal or trial -- stuck between Scylla and Charybdis,
he ultimately chose to take the higher plea deal.
Under the terms of the plea agreement, Ortiz's total
offense level as to Count I was calculated with a base offense
level of thirty (for possession of at least 3.5 but less than five
kilograms of cocaine pursuant to U.S. Sentencing Guidelines Manual
("USSG") § 2D1.1(c)(5) (U.S. Sentencing Comm'n 2012); plus two
levels for his role as a manager or supervisor pursuant to USSG
§ 3B1.1(c); plus two levels for the possession of drugs near a
public school pursuant to USSG § 2D1.2(a)(1); minus three levels
for acceptance of responsibility pursuant to USSG § 3E1.1(a)-(b).
With a resulting total offense level of thirty-one on Count I, the
applicable

Guidelines

range

was

108-135

months,

assuming

a

criminal history category of I.4
The parties agreed that a consecutive term of sixty
months' imprisonment was applicable to Count V and ultimately
agreed to a total Guidelines range of 168-180 months on both
counts,5 with the government reserving the right to request a

4

The parties did not stipulate to the applicable criminal
history category.
5

We note that in calculating the total recommended Guidelines
range the parties agreed to a range of 168-180 months on both
- 9 -

Case: 14-1693

Document: 00117169618

sentence

at

the

high

end

Page: 10

of

the

Date Filed: 06/21/2017

Guidelines

range

Entry ID: 6101151

and

Ortiz

reserving the right to request a sentence at the low end of the
Guidelines range.6

The government agreed to dismiss all remaining

counts against Ortiz and the plea agreement also contained a
waiver-of-appeals clause that barred Ortiz from appealing his
sentence

if

agreement.

sentenced

in

accordance

with

the

terms

of

the

Ortiz's change of plea hearing was held on August 6,

2012 (the same day that he signed the plea agreement).7

counts; however, when we tally the independently calculated
Guidelines ranges provided for each individual count in the plea
agreement (108-135 months on Count I and sixty months on Count V),
we would expect the total agreed-upon sentence to be between 168195 months -- fifteen months greater than the total actually agreed
to by the parties.
6

The plea agreement has several errors that were not
corrected before signing. For instance, it is clear that in the
original draft of the plea agreement, the government sought to
hold Ortiz responsible for at least two kilograms, but not more
than 3.5 kilograms, of cocaine. However, the parties edited the
plea agreement by hand to hold Ortiz responsible for at least 3.5
kilograms, but less than five kilograms of cocaine. The correlated
references to the Sentencing Guidelines were not corrected (i.e.,
instead of a reference to USSG § 2D1.1(c)(6), the proper section
utilized to arrive at a base offense level of 30 was USSG §
2D1.1(c)(5)).
Although we note the discrepancies, these
typographical errors are of no consequence to our analysis here.
7

As noted above, on appeal, Ortiz does not challenge the plea
agreement entered nor does he seek to withdraw his guilty plea.
He instead argues that the district court erred in failing to
address the merits of his ineffective assistance claim prior to
sentencing.

- 10 -

Case: 14-1693

Document: 00117169618

Page: 11

Date Filed: 06/21/2017

Entry ID: 6101151

3. Sentencing
After pleading guilty, and before sentencing, Ortiz
filed a pro se letter with the district court on November 8, 2012,
again

complaining

negotiations.

about

Dolz's

representation

during

plea

In the letter, Ortiz did not request any specific

relief beyond a "just sentence," but he again argued that Dolz
visited him only once during plea negotiations and that Dolz never
communicated with him further after that one meeting.

Ortiz

claimed that Dolz "neither advised [him] or represented [him] well"
and that "[Dolz] completely abandoned [him]."
Rivera

filed

a

sentencing

memorandum

on

In April 2013,
Ortiz's

behalf,

highlighting Ortiz's complaints from the November letter about
Dolz's representation and asserting Ortiz's ineffective assistance
claim.

In that memorandum, Rivera argued that Ortiz should be

sentenced in accordance with the original plea offer of 130-147
months.
In a hearing on April 8, 2013 (at which Dolz was not
present), Rivera discussed Ortiz's ineffective assistance claim
and indicated to the court that he wanted to renegotiate the plea
deal.

The government responded that it would not renegotiate the

plea deal.

Rivera also argued that at the time Ortiz's family

contacted him to represent Ortiz, Dolz "had not gone over to
discuss with [Ortiz] either the discovery nor [sic] a possible
plea."

The court scheduled another hearing (in fact, numerous

- 11 -

Case: 14-1693

Document: 00117169618

Page: 12

Date Filed: 06/21/2017

Entry ID: 6101151

hearings followed over the next 13 months to discuss Ortiz's
ineffective assistance claim) and instructed Dolz to be present.
The court noted that "the best thing to do is to allow Mr. Dolz to
answer [Ortiz's ineffective assistance claim], and then the Court
will make a determination."

Accordingly, Dolz eventually answered

Ortiz's claim, filing a written response to Ortiz's sentencing
memorandum prior to sentencing.

Rivera sought access to Dolz's

case files concerning Ortiz's plea negotiations, which both Dolz
and the government were ordered to (and presumably did eventually)
produce.
On April 21, 2014 a hearing took place, with Dolz
present, and Rivera sought to call him to the stand.

Dolz

responded that he was "not in a position to testify" and that he
had a conflict.8

After listening to the numerous contentions made

by the parties concerning how often Dolz visited Ortiz, whether or
not Ortiz was seeking to withdraw his guilty plea, and other issues
surrounding Ortiz's claim, the district court rescheduled the

8

Dolz specifically stated:
I am not in a position to testify, to appear.
I could argue, I could present evidence, I
could find documents, but I am in no condition
whatsoever. This is taking time. It is going
to take more time.
I am still yet under
certain jurisdictions. This is not that.
. . .
I am impeded.
the stand.

I have a conflict, if I take

- 12 -

Case: 14-1693

Document: 00117169618

Page: 13

Date Filed: 06/21/2017

Entry ID: 6101151

matter again, this time explicitly "put[ting] the case [down] for
a two-day [evidentiary] hearing."

Dolz was ordered to be present

with counsel.
On

May

21,

2014,

before

the

evidentiary

hearing

scheduled for that date got underway, Rivera filed a supplemental
memorandum further detailing Ortiz's ineffective assistance claim.
When it was his turn to address the court, Rivera repeatedly stated
that Ortiz was not seeking to withdraw his guilty plea, but that
he wanted the judge to consider Ortiz's ineffective assistance
claim in order to sentence him according to the terms of the
original plea offer of 130-147 months.

The district court, after

listening to arguments from both sides, ultimately ruled that "to
the extent that this may be a camouflaged motion to withdraw a
plea, the Court denies the request because the timing is not
proper.

[Ortiz] is not alleging that he's innocent, and to that

effect, if it is a motion to withdraw the plea, it is denied."
The district court held further that "to the extent that [Ortiz's
memorandum on ineffective assistance] is a 2255, it is premature."
At sentencing, held that very same day, Rivera also
argued that the district court should sentence Ortiz at the lower
end of the applicable Guidelines range because similarly-situated
co-defendants had received sentences of nine, ten, or eleven years.
Ultimately, the district court declined to rule on the merits of
Ortiz's ineffective assistance claim, rejected his sentencing

- 13 -

Case: 14-1693

Document: 00117169618

Page: 14

Date Filed: 06/21/2017

Entry ID: 6101151

disparity arguments, and sentenced him in accordance with the plea
agreement to a total of 174 months or 14.5 years (near the top of
the applicable Guidelines range).
After filing the instant appeal, Ortiz filed a motion to
reduce his sentence before the district court pursuant to 18 U.S.C.
§ 3582(c)(2), which was granted on December 30, 2015, during the
pendency of this appeal.
Analysis
On appeal, Ortiz primarily argues that the district
court

erred

in:

(1)

failing

to

address

the

merits

of

his

ineffective assistance claim prior to sentencing; and (2) failing
to adequately address his sentencing disparity arguments.9 Because
we ultimately remand to the district court to conduct whatever
proceedings

are

necessary

to

rule

on

Ortiz's

ineffective

assistance claim (for reasons discussed in more detail below), we
decline to delve into the merits of his sentencing disparity
argument at this time.

9

Ortiz also argues that the district court erred in ruling
on his motion for a reduction of sentence prematurely.
Both
parties agree that the district court lacked jurisdiction to rule
on the motion while this appeal was pending. See United States v.
Cardoza, 790 F.3d 247, 248 (1st Cir. 2015) ("[A] district court
does not have jurisdiction to enter a sentence modification order
under § 3582(c)(2) while an appeal of that sentence is pending").
We, therefore, vacate the district court's ruling on the sentence
reduction and remand this issue "so that the district court, once
its jurisdiction has reattached, may consider reducing [Ortiz's]
sentence."
United States v. Rodríguez-Milián, 820 F.3d 26, 36
(1st Cir.), cert. denied, 137 S. Ct. 138 (2016).

- 14 -

Case: 14-1693

Document: 00117169618

1.

Page: 15

Date Filed: 06/21/2017

Entry ID: 6101151

Waiver

As a threshold matter, we must determine whether Ortiz's
claims are barred by the waiver-of-appeals clause found in his
plea agreement.

Ortiz concedes that he entered into his plea

agreement knowingly and voluntarily.

However, he argues that the

waiver-of-appeals clause should not be enforced because to do so
would work a miscarriage of justice in that his plea negotiations
were tainted by ineffective assistance of counsel.

The government

says the waiver-of-appeals clause is enforceable because Ortiz's
ineffective assistance claim results in no miscarriage of justice
since he "may present his claim through a 2255 motion" and is
therefore not prejudiced by the court's finding that his claim was
premature.10
This court has recognized that "if denying a right of
appeal would work a miscarriage of justice, the appellate court,
in its sound discretion, may refuse to honor the waiver."

United

States v. Teeter, 257 F.3d 14, 25 (1st Cir. 2001).
In determining whether a miscarriage of justice would
result, we consider, among other factors, "the clarity of the
alleged error, its character and gravity, its impact on the
defendant, any possible prejudice to the government, and the extent

10

The government also argues that Ortiz's sentencing
disparity claim is barred by the waiver-of-appeals clause because
he knowingly and voluntarily entered into a valid plea agreement.

- 15 -

Case: 14-1693

Document: 00117169618

Page: 16

Date Filed: 06/21/2017

to which the defendant acquiesced in the result."

Entry ID: 6101151

United States

v. Pratt, 533 F.3d 34, 37 (1st Cir. 2008) (quoting United States
v. Cardona-Díaz, 524 F.3d 20, 23 (1st Cir. 2008)).

We have noted

that

been

the

miscarriage-of-justice

exception

has

applied

"sparingly and without undue generosity" and is therefore reserved
for egregious circumstances.

United States v. De-La-Cruz Castro,

299 F.3d 5, 13 (1st Cir. 2002) (quoting Teeter, 257 F.3d at 26).
Nevertheless, in Teeter, we listed, inter alia, certain categories
of

cases

which

may

fall

within

the

exception,

specifically

recognizing

appellants

claim

their

constitutionally

that

miscarriage-of-justice
"situations

sentences

impermissible

factors

were
(say,

in

which

based

on

race

or

ethnicity) . . . or that the plea proceedings were tainted by
ineffective assistance of counsel."

Teeter, 257 F.3d at 25 n.9

(internal citations omitted).
Applying those principles, we first note the unique
posture of Ortiz's argument:

Ortiz is not alleging that the

attorney who negotiated the plea deal that Ortiz actually entered
into (Rivera) provided ineffective assistance, but that his prior
attorney (Dolz) was ineffective in adequately communicating with
him regarding plea negotiations.

That below-par performance, says

Ortiz, cost him a better plea deal because it was off the table by
the time his new counsel took over his case.

Ortiz, in several

pro se filings and through memoranda filed by his second attorney,

- 16 -

Case: 14-1693

Document: 00117169618

Page: 17

Date Filed: 06/21/2017

Entry ID: 6101151

attempted to have the district court consider the detrimental
impact of his first attorney's alleged deficient performance on
the posture of his plea negotiations and resolve the ineffective
assistance claim prior to sentencing.

However, the district court

refused to rule on his claim, finding it premature.
clear

that

the

district

court

seemingly

Because it is

misunderstood

its

authority to promptly decide Ortiz's Sixth Amendment claim that
is, at least on its face, plausible because Ortiz raised his
complaint about counsel's inadequate attention before signing the
plea agreement, and because the terms of the plea agreement are
themselves arguably a product of a Sixth Amendment violation, we
believe that Ortiz's waiver falls into that narrow category of
cases we described in Teeter where enforcement would work a
miscarriage of justice.

Therefore, we exercise our discretion not

to enforce the waiver here.

See United States v. Del Valle-Cruz,

785 F.3d 48, 57 (1st Cir. 2015) (refusing to enforce a waiver where
the error was of a "constitutional dimension").

We proceed to the

merits of Ortiz's appeal.
2.

Ineffective Assistance

It is well-established that a defendant is entitled to
the Sixth Amendment right to effective assistance of counsel during
plea negotiations.

United States v. Márquez-Pérez, 835 F.3d 153,

165 (1st Cir. 2016).

And "[w]e assess a claim of ineffectiveness

in plea negotiations under the two-part test of Strickland v.

- 17 -

Case: 14-1693

Document: 00117169618

Page: 18

Date Filed: 06/21/2017

Entry ID: 6101151

Washington, 466 U.S. 668 (1984), under which a defendant must show
deficient performance and prejudice."

Id.

Deficient performance

is measured against an "objective standard of reasonableness" and
"[p]rejudice exists if there is a 'reasonable probability that,
but

for

counsel's

unprofessional

errors,

proceeding would have been different.'"

the

result

of

the

Id. (quoting Strickland,

466 U.S. at 688).
"When

we

receive

ineffective

assistance

of

counsel

claims on direct appeal, we have three options:" (1), and most
commonly,

we

can

decline

to

hear

such

claims,

allowing

the

appellant to raise the claim before the district court by means of
a 28 U.S.C. § 2255 collateral attack; (2) in more rare instances
we can rule on the merits of the claim on direct appeal where the
facts are sufficiently developed; or (3) where "the record [] is
not developed enough to decide the ineffective assistance of
counsel claim on the merits, yet it does contain sufficient indicia
of ineffectiveness in the plea agreements, the PSR, and the
transcripts of the change of plea and sentencing hearings," we may
remand the case for proceedings on the ineffective assistance claim
without requiring the defendant to bring a separate collateral
attack.

United States v. Colón-Torres, 382 F.3d 76, 84-85 (1st

Cir. 2004).
And while we have not previously ruled on the precise
issue presented here (whether a district court should rule on an

- 18 -

Case: 14-1693

Document: 00117169618

Page: 19

Date Filed: 06/21/2017

Entry ID: 6101151

ineffective assistance claim prior to sentencing and if so, under
what circumstances), as noted by Ortiz, we have indicated in the
context of claims involving attorney-client disputes that "[w]here
the accused voices objections to appointed counsel, the trial court
should inquire into the reasons for the dissatisfaction."

United

States v. Prochilo, 187 F.3d 221, 229 (1st Cir. 1999) (quoting
United States v. Allen, 789 F.2d 90, 92 (1st Cir. 1986)).
failure

to

conduct

discretion.

such

an

inquiry

constitutes

an

abuse

The
of

Id. at 229 ("In the case at bar the trial court, in

an abuse of its discretion, denied the motions for continuance and
for reconsideration without making inquiry into the accused's
concerns . . . .

Because no inquiry was made, this court has no

basis in the record for sustaining the trial court's rulings.
Accordingly, we are constrained by the Sixth Amendment to direct
that Prochilo's conviction be set aside and that this case be
remanded to the district court for further proceedings.").
We have similarly held, within the context of alleged
conflict of interest situations, "that the district court must
inquire into each instance of joint representation of multiple
defendants, and must advise each defendant of his right to separate
counsel."
Cir.

United States v. Coneo-Guerrero, 148 F.3d 44, 47 (1st

1998).

We

therefore

require

trial

courts

to

"inquire

diligently whether [defendants] have discussed the risks with
their attorney, and whether they understand that they may retain

- 19 -

Case: 14-1693

Document: 00117169618

Page: 20

Date Filed: 06/21/2017

Entry ID: 6101151

separate counsel, or if qualified, may have such counsel appointed
by the court and paid for by the government."

United States v.

Foster, 469 F.2d 1, 5 (1st Cir. 1972); see also United States v.
Cardona-Vicenty, 842 F.3d 766, 772 (1st Cir. 2016), cert. denied,
137 S. Ct. 1238 (2017) ("[G]iven the 'ubiquitous and insidious'
risks of multiple representation, the Sixth Amendment imposes a
duty on trial courts to investigate a defendant's timely objections
to joint representation and to inquire into the propriety of
multiple
reasonably

representation
should

know

whenever
that

a

the

trial

particular

court

'knows

conflict

or

exists.'"

(quoting United States v. Hernandez-Lebron, 23 F.3d 600, 603-04
(1st Cir. 1994))).

Accordingly, the importance of a district

court's inquiry into attorney-client disputes and conflicts of
interest is well established.
Two of our sister circuits have ruled on the precise
issue presented here.

See United States v. Steele, 733 F.3d 894,

897 (9th Cir. 2013); United States v. Brown, 623 F.3d 104, 112-14
(2d Cir. 2010).

In Brown, the Second Circuit held that the

district court should have ruled on an ineffective assistance claim
prior to sentencing where the defendant's first counsel (who had
been accused of ineffective assistance) had already been relieved
and the defendant was asserting that his previous counsel failed
to inform him of a 20-year plea offer.
matter

of

first

impression,

we

hold

- 20 -

623 F.3d at 112-14 ("As a
that

when

a

claim

of

Case: 14-1693

Document: 00117169618

Page: 21

Date Filed: 06/21/2017

Entry ID: 6101151

ineffective assistance of counsel is first raised in the district
court prior to the judgment of conviction, the district court may,
and at times should, consider the claim at that point in the
proceeding" and there was "no good reason to postpone inquiry into
the merits of [the defendant's] claim.").
The Second Circuit recognized that while the appellate
court typically does not hear ineffective assistance claims on
direct appeal (unless the record is sufficiently developed), a
trial court need not invoke the "appellate court's rubric and
require a defendant to use his one § 2255 motion to raise an
ineffective assistance claim post-judgment, particularly when the
district court is in a position to take evidence, if required, and
to decide the issue pre-judgment."

Id. at 113.

The Ninth Circuit has since adopted the Second Circuit's
holding, "adopt[ing] the rule in Brown that 'when a claim of
ineffective assistance of counsel is first raised in the district
court prior to the judgment of conviction, the district court may,
and at times should, consider the claim at that point in the
proceeding.'"

Steele, 733 F.3d at 897 (quoting Brown, 623 F.3d at

113) ("Though district courts have heard prejudgment ineffective
assistance of counsel claims on occasion, see, e.g., United States
v. Del Muro, 87 F.3d 1078, 1080 (9th Cir. 1996), we have not
previously articulated the standard a district court should apply
to decide whether to rule on such a claim.

- 21 -

We agree with the

Case: 14-1693

Document: 00117169618

Page: 22

Date Filed: 06/21/2017

Entry ID: 6101151

Second Circuit's decision in United States v. Brown, that a
district court need not 'invoke an appellate court's rubric and
require a defendant to use his one § 2255 motion to raise an
ineffective assistance claim post judgment, particularly when the
district court is in a position to take evidence, if required, and
to decide the issue prejudgment.'" (quoting Brown, 623 F.3d at
113)).

Nevertheless, in Steele, the Ninth Circuit affirmed the

district court's decision to reserve ruling on a defendant's
ineffective

assistance

claim

until

after

the

initiation

of

collateral proceedings because of "the lack of a significant record
necessary to adequately consider [the defendant's] broad-based
motion" and the court's consideration of "delaying the trial
proceedings to conduct an immediate hearing on an under-developed
motion."

Steele, 733 F.3d at 899.
We agree with our sister circuits and similarly hold

that "when a claim of ineffective assistance of counsel is first
raised in the district court prior to the judgment of conviction,
the district court may, and at times should, consider the claim at
that point in the proceeding."

Brown, 623 F.3d at 113.

And the

court's failure to do so may constitute an abuse of discretion.
See id. at 112 ("The government argues unconvincingly that given
the Supreme Court's and this Court's general aversion to deciding
ineffective assistance claims on direct review, 'the district
court's refusal to entertain [the defendant's] motion before he

- 22 -

Case: 14-1693

was

Document: 00117169618

sentenced

cannot

be

Page: 23

deemed

Date Filed: 06/21/2017

an

abuse

of

Entry ID: 6101151

discretion.'

We

disagree.").
As noted by the Second Circuit, "[w]e are mindful that
district courts face competing considerations in deciding whether
it is appropriate to inquire into the merits of such claims prior
to judgment, including principally the potential disruption of the
proceedings, especially if the attorney against whom the complaint
is directed continues at the time to represent the defendant."
Id. at 113. We similarly observe that "[t]he decision to interrupt
the pre-judgment proceedings to inquire into the merits of an
ineffective assistance of counsel claim may depend on, among other
things, whether the court would need to relieve the defendant's
attorney, or in any event, to appoint new counsel in order to
properly adjudicate the merits of the claim."

Id.

The court may

also take into consideration whether the defendant's "claim [is]
broad-based and the evidentiary record to consider it [is] sorely
lacking," as well as "whether the interests of justice and judicial
economy would be served by delaying the trial proceedings to
conduct

an

immediate

hearing

on

an

under-developed

motion."

Steele, 733 F.3d 898-99.
Having outlined the proper standards applicable, we now
turn to the particular facts of Ortiz's case.

Ortiz argues that

his first counsel was ineffective in failing to timely communicate
that his counteroffer had been rejected, that the original plea

- 23 -

Case: 14-1693

Document: 00117169618

offer

had

expired,

concerning

plea

and

Page: 24

by

Date Filed: 06/21/2017

failing

negotiations

to

adequately

whatsoever

after

Entry ID: 6101151

communicate

Ortiz

made

an

initial counteroffer.
As we detailed earlier, Ortiz raised his concerns at
multiple points in the proceeding, providing the district court
with

several

opportunities

assistance claim.

to

address

Ortiz's

ineffective

Based upon the facts of this case, we conclude

that the district court had "no good reason to postpone inquiry
into the merits of [Ortiz's] claim" and thus abused its discretion
in doing so.

Brown, 623 F.3d at 113.

Like Brown, the only proceeding that would have been
postponed

or

ineffectiveness

interrupted
during

by

plea

an

inquiry

negotiations

into
would

the

alleged

have

been

sentencing and the attorney against whom the complaint was directed
(Dolz) had already been relieved of his duties since July 2012.
Furthermore, the court had already scheduled and heard detailed
arguments on the issue, rescheduling several sentencing hearings
as

needed.

Additionally,

unlike

Steele,

the

record

was

significantly developed by the time of sentencing, especially
since the district court had heard from both sides and had required
both

Dolz

and

the

government

to

turn

over

their

case

files

detailing the facts surrounding plea negotiations.11 Consequently,

11

We note that when Rivera attempted to call Dolz as a witness
during one of the hearings, Dolz refused to take the stand,
- 24 -

Case: 14-1693

Document: 00117169618

Page: 25

Date Filed: 06/21/2017

Entry ID: 6101151

the district court was well-positioned to decide the merits of
Ortiz's claim without a sacrifice to judicial economy.
In addition to these procedural considerations, there
were also several factors indicating the facial plausibility of
Ortiz's

ineffective

assistance

claim

including:

the

parties'

dispute regarding how often Dolz communicated with Ortiz and the
nature of those communications; the lack of clarity around when
the

original

130-147

month

offer

expired;

Ortiz's

consistent

statements that he always desired to accept a plea and was only in
search of the best deal; and Ortiz's assertion that Dolz never
fully explained the nature of the offenses lodged against him
during the course of negotiations.12
As the Supreme Court has noted, the "plea-bargaining
process is often in flux, with no clear standards or timelines and
with

no

judicial

supervision

prosecution and defense."
(2012).

of

the

discussions

between

Missouri v. Frye, 566 U.S. 133, 143

Yet, "[n]inety-seven percent of federal convictions and

ninety-four percent of state convictions are the result of guilty
pleas."

Id.

With such wide-sweeping impact despite the existence

claiming he had a conflict, presumably with Ortiz. We are puzzled
as to how such a conflict would excuse him from testifying in this
circumstance.
12

We also note that the record indicates that Dolz was ill
at some point during his representation of Ortiz and was "out of
commission" for at least ninety days.

- 25 -

Case: 14-1693

Document: 00117169618

Page: 26

Date Filed: 06/21/2017

Entry ID: 6101151

of ambiguity around the standards to be maintained in the pleabargaining process, it may be imperative for a district court, at
times, to rule on a claim of ineffective assistance prior to the
defendant seeking post-conviction relief.

Such is true here.

If

Dolz were found to have provided ineffective assistance in his
failure to communicate with Ortiz during plea negotiations, the
district court would be required to place Ortiz in the position he
would have been had Dolz been effective.

See Brown, 623 F.3d at

114 ("[I]f counsel is determined to have been ineffective, equities
require that the defendant be put in the same place he would have
been but for counsel's ineffective assistance.").
if

the

district

court

had

determined

In other words,
that

counsel's

ineffectiveness caused Ortiz to be unaware of a plea offer that he
would have accepted had he a chance to do so, then the district
court should have given Ortiz that chance.

On the other hand, if

the court had determined that Dolz was not ineffective (as a
reminder,

to

establish

ineffective

assistance

Ortiz

must

demonstrate both deficient performance and that he was prejudiced
by that performance), then Ortiz would have been stuck with the
plea agreement he actually entered into.
Conclusion
Having determined that the district court abused its
discretion in failing to rule on the merits of Ortiz's ineffective
assistance

claim

prior

to

sentencing,

- 26 -

we

remand

for

further

Case: 14-1693

Document: 00117169618

Page: 27

Date Filed: 06/21/2017

Entry ID: 6101151

proceedings consistent with this decision and retain jurisdiction
over any remaining claims.13

13

Because we remand for further proceedings, we need not
decide now Ortiz's sentencing disparity claim. See United States
v. González-Vélez, 466 F.3d 27, 38 (1st Cir. 2006) (declining to
rule on the merits of an appellant's other sentencing claims after
remanding on the basis of one of his claims).

- 27 -