Chillemi v. The Town of Southampton et al

Filing 94

ORDER granting in part and denying in part 80 Motion for Summary Judgment. For the reasons set forth herein, the Court grants defendants' motion for summary judgment on the compelled self-incrimination claim and on all claims as to defendant Thomas Tully, and denies the motion in all other respects. Ordered by Judge Joseph F. Bianco on 12/20/2017. (Baum, Sabrina) (Main Document 94 replaced on 12/20/2017) (Bollbach, Jean).

UNITED STATES DISTRICT COURT
EASTERN DISTRICT OF NEW YORK
_____________________
No 12-CV-3370 (JFB)(AKT)
_____________________

CRAIG J. CHILLEMI,
Plaintiff,
VERSUS

THE TOWN OF SOUTHAMPTON, ERIC SICKLES,
JAMES KIERNAN, AND THOMAS TULLY,
Defendants.
___________________
MEMORANDUM AND ORDER
December 20, 2017
___________________

JOSEPH F. BIANCO, District Judge:
Plaintiff Craig Chillemi (“Chillemi” or
“plaintiff”) brings this action against
defendants the Town of Southampton (“the
Town”) and Officer Eric Sickles (“Officer
Sickles” or “Sickles”), Lieutenant James
Kiernan
(“Lieutenant
Kiernan”
or
“Kiernan”), and Detective Thomas Tully
(“Detective Tully” or “Tully”) (together with
the Town, “defendants”), arising out of
Officer Sickles’s arrest of Chillemi on July 8,
2009 in Hampton Bays, New York. Chillemi
brings claims pursuant to 42 U.S.C. § 1983
(“Section 1983” or “§ 1983”) for the alleged
violations of his Fourth, Fifth, and Fourteenth
Amendment rights. Chillemi asserts claims
1

In his opposition, Chillemi clarifies that he did not
intend to bring an Equal Protection claim. (Pl.’s Mem.
of Law in Opp. to Mot. for Summary Judgment (“Pl.’s
Mem.”), ECF No. 83, at 18.)
Chillemi’s complaint also included a conspiracy claim
brought under 42 U.S.C. § 1985(3), (Compl.
¶¶ 55-58), which the Court dismissed for failure to

for
false
arrest/false
imprisonment,
unreasonable search and seizure, fabrication
of evidence, compelled self-incrimination,
and Monell liability.1 More specifically, in
connection with his arrest for unlicensed
operation of a motor vehicle and possession
of a controlled substance, plaintiff alleges
that defendants fabricated evidence against
him in order to end his relationship with
Detective Tully’s daughter. (See Decl. in
Opp. re Mot. for Summary Judgment, ECF
No. 81, “Chillemi Decl.,” at ¶ 26 (“Officer
Sickles, Lieutenant Kiernan, and Detective
Tully fabricated evidence that led to my
arrest and the subsequent charges brought
against me in an attempt to end my
state the requisite “racial, or perhaps otherwise classbased, invidiously discriminatory animus behind the
conspirators’ action,” Chillemi v. Town of
Southampton, 943 F. Supp. 2d 365, 382 (E.D.N.Y.
2013) (quoting Arteta v. County of Orange, 141 F.
App’x 3, 8 (2d Cir. 2005)).

relationship with Tara Tully. The evidence
they fabricated was: that I was driving a
vehicle, had drugs in my possession, and
made incriminating statements. I did not
make any incriminating statements; I was not
driving a vehicle; and I did not possess any
drugs at the time of my false arrest. Anything
to the contrary was fabricated.”).)

Sickles on fabricated misdemeanor charges
of unlicensed operation of a motor vehicle
and possession of cocaine because Sickles
did not like the fact that Chillemi was dating
Tara Tully (“Tara”2), who is the daughter of
Detective Tully. More specifically, Chillemi
has submitted a sworn statement that he was
not even driving the vehicle on the night in
question, and that Sickles also falsely
claimed that he had a bag of cocaine in his
possession. Tara also has stated under oath
that she was driving the car, not Chillemi.
Thus, plaintiff has created a genuine issue of
disputed fact as to whether there was
probable cause for Sickles to arrest him on
July 8, 2009. Those same disputed issues of
fact preclude summary judgment on the
claim that the pat-down at the time of his
arrest was an unconstitutional search, as well
as on the fabrication of evidence claim
relating to the allegations that Sickles falsely
claimed that Chillemi was driving the
vehicle, had cocaine in his possession, and
confessed.

Presently before the Court is defendants’
motion for summary judgment pursuant to
Federal Rule of Civil Procedure 56. For the
reasons set forth in detail below, the Court
grants the motion on the compelled selfincrimination claim and on all claims against
Tully, but denies the motion in all other
respects because of genuine disputes of
material fact that exist with respect to the
remaining claims against defendants Sickles,
Kiernan, and the Town.
In particular, as a threshold matter, the
Court concludes that, although defendants
argue that the claims are barred by Chillemi’s
guilty plea to lesser charges arising from the
arrest, construing the evidence most
favorably to plaintiff, his guilty plea may
have been involuntary because plaintiff may
have entered the plea based upon the
erroneous belief that his plea would not
impact his ability to remain in the work
release program. Plaintiff has stated that he
entered the plea based upon that
understanding and the colloquy at the plea
proceeding, which certainly creates an
ambiguity as to whether such an
understanding among the parties to that effect
existed.
Thus, plaintiff has set forth
sufficient evidence to create a disputed issue
of material fact that precludes summary
judgment on this issue.

Although defendants argue that Kiernan
is entitled to summary judgment because he
had no personal involvement in the allegedly
unconstitutional actions by Sickles, the Court
disagrees. There is evidence that Kiernan
arrived at the scene shortly after the arrest and
administered the oath for the General Traffic
Complaint and Misdemeanor Information
signed by Sickles on July 8, 2009. As to
Kiernan’s knowledge of the allegedly
unconstitutional nature of Sickles’s search
and arrest, plaintiff relies upon the
involvement of both Sickles and Kiernan in
his 2007 arrest and the circumstances
surrounding that encounter, as well as the fact
that Tara told Chillemi that Kiernan is her
godfather. Moreover, Chillemi disputes
Kiernan’s claim that, during the July 2009

With respect to the false arrest claim,
plaintiff argues that he was arrested by
2

To prevent confusion with defendant Thomas Tully,
the Court refers to Tara Tully by her first name.
2

arrest, Chillemi tried to make a deal with him
to avoid arrest. Thus, Chillemi asserts that
Kiernan fabricated incriminating statements
by Chillemi at the scene of the arrest.
Construing the evidence most favorably to
plaintiff, there is an issue of fact as to whether
Kiernan was aware that Sickles was
fabricating evidence against Chillemi on July
8, 2009 and failed to intervene to prevent the
alleged constitutional violation, and whether
Kiernan fabricated incriminating statements
by Chillemi.

responsible for the alleged unconstitutional
acts of Sickles on July 8, 2009.
Finally, because plaintiff does not allege
that he made any statements to the police
following his arrest, he cannot have a
compelled
self-incrimination
claim.
Although he does assert that Sickles
fabricated a confession in order to support the
arrest, that allegation should proceed (as
noted above) as a fabrication of evidence
claim. Accordingly, summary judgment is
granted on the compelled self-incrimination
claim.

These same disputed issues of fact
preclude summary judgment in favor of
defendants Sickles and Kiernan at this stage
on grounds of qualified immunity. In other
words, if a rational jury credits plaintiff’s
version of the events and finds that Sickles
fabricated evidence against Chillemi during
the course of an unconstitutional search and
arrest, and Kiernan became aware of the
unconstitutional nature of the arrest and
failed to intercede at the scene to prevent any
further unlawful detention, no qualified
immunity would exist for either defendant.

I. BACKGROUND
A. Factual Background
The Court takes the following facts from
Chillemi’s and defendants’ respective Rule
56.1 Statements of Fact, and any admissible
affidavits, depositions, and exhibits.3 The
Court construes the facts in the light most
favorable to Chillemi, the nonmoving party.
See Capobianco v. City of New York, 422
F.3d 47, 50 n.1 (2d Cir. 2005). Where only
one party’s Rule 56.1 Statement is cited, the
other party does not dispute the facts alleged
or has offered no admissible evidence to
refute that fact.

With respect to defendant Tully, the
Court concludes that summary judgment is
warranted in his favor on all claims because
there is simply no evidence in the record of
his personal involvement in any of the
alleged unconstitutional acts by Sickles, or
that he was in a position to intercede during
the arrest. Although plaintiff speculates that
he may have been involved because of an
alleged desire to prevent his daughter from
dating Chillemi, such speculation is
insufficient to overcome a motion for
summary judgment.
In short, even
construing the evidence most favorably to
plaintiff, no rational jury could find Tully

1. Background Information
Plaintiff alleges that his relationship with
Detective Tully’s daughter, Tara, and
Sickles’s desire to date Tara, led to his being
targeted for arrest by defendants, both in
2007 and in 2009.
At the time of the relevant arrests in this
case, Chillemi was involved in a romantic
relationship with Tara. (Defendants’ Rule
56.1 Statement (“Defs.’ 56.1”) ¶¶ 2, 25, 29,
42, 53.) Tara was the “estranged” daughter

3

Although the Rule 56.1 Statements of Fact (“56.1
statements”) contain specific citations to the record,

the Court cites primarily to the statements rather than
to the underlying citations.
3

Street Crimes Unit (“SCU”), and Kiernan
was the supervising sergeant of the SCU
during this period. (Id. ¶¶ 12, 14.) Tully had
previously worked in the SCU, but was a
detective in another unit during the relevant
period. (Id. ¶ 12; Defs.’ Mem., Ex. L
(“Thomas Tully Tr.”) at 8-9.)

of defendant Tully, a detective in the police
unit that arrested Chillemi in 2007 and again
in 2009. (Id. ¶¶ 1, 7, 26, 29, 51, 59, 63.)
Chillemi never met or interacted with
defendant Tully. (Defs.’ 56.1 ¶ 4.) Although
Tully was not involved in the investigation
into Chillemi’s alleged drug sales or either of
his arrests, (id. ¶¶ 106-07), Chillemi alleges
that Sickles “arrested Chillemi because
Chillemi was dating a police officer’s
daughter,” (Plaintiff’s Rule 56.1 Statement
(“Pl.’s 56.1”) ¶ 90). Chillemi more broadly
attributes this motive to all defendants,
“claim[ing] that he was arrested due to the
defendants’ disapproval of his romantic
relationship with Defendant Tully’s
daughter.” (Defs.’ 56.1 ¶ 99.)

Tara stated that she knew Kiernan
through her father. (Defs.’ 56.1 ¶ 7.) Kiernan
also admitted this connection with Tara, and
that he “kn[ew] that she was Chillemi’s
girlfriend at the time of the underlying
events.” (Id. ¶¶ 8-9.) Kiernan said that he did
not, however, “know [Tara] on a personal
level.” (Id. ¶ 9.) Sickles stated that he knows
Tara as Tully’s daughter, and “knew of” Tara
in August 2007. (Id. ¶ 11.) Defendants assert
that Tully never had conversations with
Kiernan or Sickles about Tara dating
Chillemi. (Id. ¶¶ 102, 104.)

Tara was not only estranged from her
father, but she also had not lived with him
since she was born. (Id. ¶ 100.) Tully claims
that he did not know Chillemi and Tara were
dating until after Chillemi’s 2009 arrest, (id.
¶ 101), but Tara disputes this fact, (Pl.’s 56.1
¶ 101 (citing Defs.’ Mem. of Law in Supp. of
Mot. for Summary Judgment (“Defs.’
Mem.”), ECF No. 80, Ex. M (“Tara Tully
Tr.”) at 72 (claiming “[her father] knew” they
were dating in 2009))).

Chillemi also alleges that his arresting
officer (Sickles) had a romantic interest in
Tara. (Pl.’s 56.1 ¶ 90 (explaining that
“Sickles arrested Chillemi because . . .
Sickles ha[d] a romantic interest in Tara
Tully; Sickles asked Tara Tully on a date both
before and after Chillemi’s 2009 arrest”);
Defs.’ 56.1 ¶ 91.) Tara testified that she had
a couple of interactions with Sickles after
Chillemi’s
arrest
that
made
her
“uncomfortable,” and that Sickles “asked her
out on a date ‘like twice.’” (Defs.’ 56.1
¶¶ 92-93.) She said that she did not take it
entirely seriously, but it made her feel
uncomfortable. (Id. ¶ 93.)

Tully was not involved in any
investigation into Chillemi’s alleged drug
sales, (Defs.’ 56.1 ¶ 106), and he was not
present at the scene of either of Chillemi’s
arrests by the Southampton Town Police
Department (“SHTPD”), (id. ¶ 107).
Although it is uncontroverted that Tully had
no involvement in Chillemi’s arrests,
Chillemi disputes the claim that Tully had no
knowledge of Chillemi prior to this lawsuit.
(Pl.’s 56.1 ¶ 99.)

2. Chillemi’s August 2007 Arrest
Chillemi was first arrested by the SHTPD
on August 5, 2007 and charged with several
counts of drug possession and sale. (Id.

The three individual defendants were all
members of the SHTPD, which was the
department involved in the arrest of Chillemi
both in 2007 and 2009. (Defs.’ 56.1 ¶¶ 7, 12,
14.) Kiernan and Sickles both worked in the
4

¶¶ 25, 29, 34.) It was while furloughed4 from
his resulting 2007 sentence that Chillemi was
arrested again in 2009, by the same police
unit, and subjected to the alleged civil rights
violations that gave rise to the instant
complaint. (Id. ¶ 52.)

this fact, contending that Tara had not been
arrested in the first place. (Id. ¶ 29.)
Tully was not present at the raid on the
house or at the police station. (Id. ¶ 30.)
Tara has no knowledge that her father was
“involved in any way,” or that charges were
brought against Chillemi because her father
wanted to end their relationship. (Id.) As to
defendant Kiernan’s involvement, it is
undisputed that Kiernan did not talk to Tara
at the time of this first arrest. (Id. ¶ 32.)

The SHTPD unit that arrested Chillemi
both times was the SCU, a plain-clothes,
primarily narcotics unit.5 (Id. ¶ 12.) The
SCU began investigating Chillemi in 2007
for “doing drugs and selling drugs” out of his
home in Southampton. (Id. ¶¶ 21-22.)
Undercover SCU officers purchased cocaine
from Chillemi “[o]n two or three separate
occasions.” (Id. ¶ 23.) The Town then
obtained a search warrant, and the SCU and
the Town’s Emergency Services Unit
(“ESU”) executed a lawful search of
Chillemi’s home on August 5, 2007.6 (Id.
¶¶ 24-27.)

The police recovered “heroin, cocaine,
and some pills” from their 2007 search. (Id.
¶ 34.) Chillemi pleaded guilty to the sale of
a controlled substance and criminal
possession of a controlled substance in the
third degree and was sentenced to four years
in prison. (Id. ¶ 35.) Chillemi never made
complaints to the SHTPD about “anything
that happened in the course of his August 5,
2007 arrest before pleading guilty.” (Id.
¶ 36.)

At the time of his 2007 arrest, Chillemi
was living with Tara7 and two other
roommates. (Id. ¶ 25.) Chillemi and Tara
were home along with one of their
roommates and another man when “at least
ten” police officers from the SCU and ESU
arrived at their house to execute the search
warrant. (Id. ¶¶ 26-27.) Chillemi was the
first removed from the house; Sickles
arrested him. (Id. ¶ 31.) Defendants assert
that all four occupants were arrested, and that
Tara was brought to the police station,
questioned, and processed, but was not
charged. (Id. ¶¶ 29, 32.) Chillemi disputes

3. Furloughed on Work Release
Chillemi was furloughed in or around
March or April 2009 and entered a work
release program. (Pl.’s 56.1 ¶¶ 37, 40; see
also supra note 5.) Before his release,
Chillemi completed a six-month drug
counseling/rehabilitation program. (Defs.’
56.1 ¶ 38.) Chillemi was required to have a
stable address in order to participate in the
program. (Id. ¶ 41.) When Chillemi was
released, he and Tara began living together in
Manorville, NY, and he began working full-

4

Defendants adopted Chillemi’s terminology from his
56.1 statement—Chillemi explained that “furlough”
rather than “parole” was the correct term to describe
his release from prison—thereby resolving the dispute
between the parties’ statements of facts. (Defs.’ Mem.
at 3 n.3.)

fact, (Pl.’s 56.1 ¶ 12). This dispute is immaterial to
resolution of the instant motion.
6

Chillemi does not challenge the legality of the 2007
search. (Id. ¶ 36.)
7
Chillemi and Tara began dating in February 2007,
and started living together in or around April of that
year. (Defs.’ 56.1 ¶¶ 2-3.)

5

Defendants claim in their 56.1 statement that the
SCU was disbanded in 2011 due to a personnel
shortage, (Defs.’ 56.1 ¶ 12), but Chillemi disputes this
5

time in an industrial cleaning job. (Id. ¶¶ 4244.) Chillemi began to earn additional free
time and was eventually home for five days
for every two nights that he had to return to
Lincoln Correctional Facility. (Id. ¶ 45.)
During this period, Chillemi reported to a
parole officer or “somebody like a parole
officer.” (Id. ¶¶ 47; Pl.’s 56.1 ¶ 47.)

a suspended license at the time; rather, he has
submitted a sworn statement that he had a
valid interim license in his pocket that “was
completely disregarded by Officer Sickles.”
(Chillemi Decl. ¶¶ 12, 14.) Moreover,
Chillemi disputes that he was driving the car
at all on the day in question and, instead,
asserts that Tara was driving. (Id. ¶ 13.) Tara
also has testified that she was driving the
vehicle on July 8, 2009, not Chillemi. (Tara
Tully Tr. at 45.) Chillemi further asserts that
he and Incardona went into Incardona’s
house when they returned from lunch, and
that Tara waited outside in the car for a
couple of minutes before an unmarked police
car pulled up to the house. (Id. ¶¶ 55-56.)

4. Chillemi’s July 2009 Arrest
According to defendants, Sickles became
aware that Chillemi was no longer
incarcerated during the summer of 2009;
informants told undercover officers that
Chillemi was out of prison and dealing drugs
again. (Defs.’ 56.1 ¶¶ 48, 50.) The SCU
identified Chillemi as “a relatively big drug
dealer,” so he was “never off their radar.”
(Id. ¶ 49.)

Contrary to Chillemi, Sickles states that
he followed Chillemi and caught up to him
“as Chillemi arrived at Incardona’s house.”
(Defs.’ 56.1 ¶ 61.) Sickles further contends
that he got out of the car, had a conversation
with Chillemi, and placed Chillemi under
arrest for aggravated unlicensed operation of
a motor vehicle. (Id. ¶¶ 62-63.) The exact
timing is unclear, but when the SHTPD ran
Chillemi’s license after his arrest, it was
listed
as
“suspended.”
(Id.
¶ 60 (citing Defs.’ Mem., Ex. F (“NYSID
Report”) at 2).) Chillemi, as noted above,
claims that his license was not suspended at
the time of the July 8, 2009 arrest. (Pl.’s 56.1
¶ 57.)

On July 8, 2009, Chillemi was out on
furlough. (Id. ¶ 52.) Chillemi went out to
lunch with Tara and a friend, Jason
Incardona, and then Chillemi and Tara drove
Incardona back to his house after lunch. (Id.
¶¶ 53, 54.) The group drove to and from
lunch in a car that Chillemi had rented, but
which Chillemi claims Tara drove even
though she was not on the rental agreement.
(Id. ¶¶ 53, 54; Pl.’s 56.1 ¶ 58.)
Here, the versions of events diverge:
Sickles asserts that he observed Chillemi
driving, with Tara in the passenger seat.
(Defs.’ 56.1 ¶ 58.) Defendants also contend
that the SHTPD had run Chillemi’s license a
few days earlier and it had come back
suspended. (Id. ¶ 60.) The SHTPD had tried
to follow Chillemi on another occasion, and
Sickles asserts that he knew that Chillemi had
a suspended license on the date of his arrest.
(Id. ¶¶ 59-60.) Chillemi disputes that he had

Sickles further asserts that he then
searched Chillemi incident to arrest and
found a bag of cocaine inside Chillemi’s right
side pants pocket.8 (Defs.’ 56.1 ¶¶ 63-64.)
Chillemi disputes Sickles’s account; he
claims that “Officer Sickles did not find a bag
of cocaine on [him] after a search incident to
his arrest; Sickles produce [sic] a baggy with
white powder in it.” (Pl.’s 56.1 ¶ 62.)

8

Sickles, therefore, added a charge of criminal
possession of a controlled substance to the other
charges. (Id. ¶ 63.)
6

Chillemi also contends that Sickles told him
that “he had waited to arrest [him] until [he]
was with Tara Tully.” (Chillemi Decl. ¶ 16.)

to headquarters for processing, (id. ¶ 71), and
Tara was sent home, (id. ¶ 72).
6. Sickles’s Alleged Proposition and the
SCU’s “Sign Off”9 on the Arrest

5. Chillemi’s Alleged Post-Arrest
Statements

Chillemi also asserts that Sickles spoke to
Tara in a condescending way during the
arrest. (Id. ¶ 91.) Chillemi further states that
Sickles was propositioning Tara for a date,
and that he said “something to the effect of,
‘hey, after this do you want to get something
to eat?’” (Id.) Chillemi contends that Sickles
had seen him driving a few times before his
arrest, but had waited until Tara “was there to
see it” to arrest him. (Id. ¶ 94.) Chillemi also
asserts that Sickles told him “something to
the effect of, ‘I can’t believe you are home
[from prison] so soon.’” (Id.)

By the time defendant Kiernan reported
to the scene, Chillemi was already
handcuffed and under arrest. (Defs.’ 56.1
¶¶ 66-67.) Kiernan asserts that he was aware
that Incardona, who lived in the house where
the arrest took place, was addicted to pills.
(Id. ¶ 66.) Sickles showed Kiernan the bag of
drugs he had found on Chillemi. (Id. ¶ 67.)
Kiernan contends that Chillemi “asked to
speak with [him], and was trying to cut a deal
so he wouldn’t be arrested and reported to the
work release program.” (Id. ¶ 68.) In
addition, according to defendants, “Chillemi
made oral admissions at the scene at the time
of the arrest; Sickles prepared a
supplementary report memorializing them.
Chillemi said: ‘I don’t even think that coke
is real. I made a fake bag up for someone.’
The second admission was made to Kiernan,
but Sickles overheard it: ‘I’m just getting
started again. I barely have an ounce.’”
(Defs.’ 56.1 ¶ 70.) Chillemi disputes these
facts, and asserts that he made no such
statements to Sickles or Kiernan. (Pl.’s 56.1
¶¶ 68-70 (citing Defs.’ Mem., Ex. H
(“Chillemi Tr.”) at 48:2-13, 56:13-21;
Chillemi Decl. ¶ 17.)

Chillemi further alleges that defendants
Kiernan and Tully “knew that the statements
made by Officer Sickles in the General
Traffic Complaint and Misdemeanor
Information were knowingly false.” (Compl.
¶¶ 32-33.) These statements included that
Sickles had seen Chillemi driving the car
(rather than Tara), and that he found a bag of
cocaine in Chillemi’s pocket. (Compl. ¶¶ 2829.)
Chillemi contends that Kiernan
supervised Sickles and “signed off” on
Sickles’s improper conduct, including when
Sickles “pull[ed] up on private property
without probable cause and ma[de] false
claims against him.” (Defs.’ 56.1 ¶ 87.)
Kiernan administered the oath on the General
Traffic Complaint. (Chillemi Decl., Ex. 2.)
Chillemi also alleges that Tully was a
supervisory officer who “knowingly
acquiesced” to Sickles’s unlawful arrest. (Id.
¶ 88.) Chillemi believes that Sickles worked
under Tully, and that the arrest “amounted to
Tully’s personal wishes being carried out.”
(Id.) Offering further support for his claims

Chillemi was charged with possession of
cocaine and aggravated unlicensed operation
of a motor vehicle, both misdemeanors.
(Defs.’ 56.1 ¶ 75.) Chillemi was transported

9

Chillemi objects to the facts presented in this section
of defendants’ 56.1 statement to the extent that they

call for a legal conclusion, but he does not object to the
content of the statements. (Pl.’s 56.1 ¶¶ 87-88.)
7

that defendants were aware of the
impropriety of the arrest, Chillemi states that
he heard other officers say that “they had to
arrest Chillemi because he was dating a cop’s
daughter.” (Id. ¶ 89.)

(Defs.’ Mem., Ex. G (“Tr. of Plea”) at 4.)
Defense counsel also stated at a later point in
the plea hearing that, after the sentence,
Chillemi “should be sent back to the work
release program.” (Id. at 5.) Moreover,
Chillemi simply uttered the word “guilty”
after reference to statutory citations for “two
violations,” and did not explain what he did
that made him guilty of those violations. (Id.)

7. Chillemi’s Plea Deal and Removal From
Work Release
Chillemi was incarcerated for three and a
half months while awaiting disposition of the
charges from his 2009 arrest. (Id. ¶ 75.)
Chillemi did not go to trial but instead, on or
around October 29, 2009, pleaded guilty to
unlawful possession of marijuana and
facilitating aggravated unlicensed operation
of a motor vehicle. (Id. ¶ 78.) Chillemi
claims that his plea was not voluntary, and
that he took the plea because, “as it was
explained to him by the judge in the Court, he
would be able to return to the work release
program.” (Id. ¶ 79.)

After his plea, Chillemi was sent back to
Lincoln Correctional Facility. (Defs.’ 56.1
¶ 83.) After two weeks, he was given a
hearing before the Temporary Release
Committee10 (“TRC”) at which an officer
read the July 8, 2009 arrest report, including
the original charges. (Id. ¶ 84.) Chillemi
tried to explain that he did not plead guilty to
a felony or misdemeanor, and that “he
expected to be reinstated to work release
because he was doing so well there.” (Id.)
The TRC denied this request, and Chillemi
was sent back to prison. (Id. ¶ 85.) Chillemi
appealed the decision, but was unsuccessful.
(Id. ¶ 86.)

The transcript shows that, during the plea,
defense counsel (Mr. Ghanayem) stated for
the record that the disposition was generous
and made reference to the fact that Chillemi
wanted to return to the work release program,
and the prosecutor (Mr. Mashhadian)
confirmed the accuracy of defense counsel’s
statement:

Chillemi was ultimately released early on
or about December 31, 2010, due to time
credited while awaiting disposition of the
charges stemming from his 2009 arrest. (Id.)
Defendants claim that Chillemi “didn’t serve
any additional jail time as a result of the July
8, 2009 arrest.” (Id.) Chillemi disputes this
statement, clarifying that although no days
were added to his 2007 sentence, his work
release privilege was suspended as a result of
this arrest. (Pl.’s 56.1 ¶ 86.) As is relevant
to the parties’ dispute over the validity of
Chillemi’s guilty plea, the period between
Chillemi’s July 8, 2009 arrest and his release

Mr. Ghanayem: And Your Honor, I
would also like to put on the record
that this is a generous disposition and
it gives my client -- to maintain a
work release program, which he has
been doing very well in. We have
talked about this with his family and
he is very anxious to get back to that.
. . . I just wanted to make sure that I
recorded that.
Mr. Mashhadian: That’s correct.
10

Defendants adopted Chillemi’s terminology from
his 56.1 statement—Chillemi explained that the
correct term is TRC rather than “parole board”—

thereby resolving the dispute between the parties’
statements of facts. (Defs.’ Mem. at 4-5.)
8

Schenectady, 728 F.3d 149, 154 (2d Cir.
2013). The moving party bears the burden of
showing that he is entitled to summary
judgment. See Huminski v. Corsones, 396
F.3d 53, 69 (2d Cir. 2005). “A party asserting
that a fact cannot be or is genuinely disputed
must support the assertion by: (A) citing to
particular parts of materials in the record,
including
depositions,
documents,
electronically stored information, affidavits
or declarations, stipulations (including those
made for purposes of the motion only),
admissions, interrogatory answers, or other
materials; or (B) showing that the materials
cited do not establish the absence or presence
of a genuine dispute, or that an adverse party
cannot produce admissible evidence to
support the fact.” Fed. R. Civ. P. 56(c)(1).
The court “is not to weigh the evidence but is
instead required to view the evidence in the
light most favorable to the party opposing
summary judgment, to draw all reasonable
inferences in favor of that party, and to
eschew credibility assessments.” Amnesty
Am. v. Town of West Hartford, 361 F.3d 113,
122 (2d Cir. 2004) (quoting Weyant v. Okst,
101 F.3d 845, 854 (2d Cir. 1996)); see also
Anderson v. Liberty Lobby, Inc., 477 U.S.
242, 248 (1986) (summary judgment is
unwarranted if “the evidence is such that a
reasonable jury could return a verdict for the
nonmoving party”).

from prison on December 31, 2010 was
approximately a year and a half.
B. Procedural Background
Chillemi commenced this action before
the Honorable Arthur D. Spatt on July 9,
2012. Defendants filed a motion to dismiss
for failure to state a claim on August 30,
2012. Chillemi filed his opposition on
October 5, 2012; defendants replied on
November 8, 2012; and the Court issued its
decision on the motion, granting it in part and
denying it in part, on May 4, 2013.
Specifically, the Court denied defendants’
motion to dismiss Chillemi’s 42 U.S.C.
§ 1983 claims, but granted defendants’
motion to dismiss his possible claims
stemming from the August 5, 2007 arrest
and/or March 28, 2008 conviction and his 42
U.S.C. § 1985(3) conspiracy claims.
Defendants answered the complaint on
May 23, 2013. Defendants filed a motion for
summary judgment on September 23, 2016.
Chillemi filed his opposition to the motion
for summary judgment on November 7,
2016, and defendants replied in support of
their motion on November 22, 2016. Judge
Spatt recused himself on March 3, 2017,
denying the pending motion for summary
judgment without prejudice and with leave to
renew upon reassignment of the case. The
case was reassigned to the undersigned, and
defendants renewed their motion for
summary judgment on March 21, 2017. The
Court held oral argument on June 6, 2017.
The matter is fully submitted.

Once the moving party has met its
burden, the opposing party “must do more
than simply show that there is some
metaphysical doubt as to the material facts
. . . . [T]he nonmoving party must come
forward with specific facts showing that there
is a genuine issue for trial.” Caldarola v.
Calabrese, 298 F.3d 156, 160 (2d Cir. 2002)
(alteration in original) (quoting Matsushita
Elec. Indus. Co. v. Zenith Radio Corp., 475
U.S. 574, 586-87 (1986)). As the Supreme
Court stated in Anderson, “[i]f the evidence
is merely colorable, or is not significantly
probative, summary judgment may be

II. STANDARD OF REVIEW
Pursuant to Federal Rule of Civil
Procedure 56(a), a court may grant a motion
for summary judgment only if “the movant
shows that there is no genuine dispute as to
any material fact and the movant is entitled to
judgment as a matter of law.” Fed. R. Civ. P.
56(a); see also Gonzalez v. City of
9

granted.” 477 U.S. at 249-50 (citations
omitted). Indeed, “the mere existence of
some alleged factual dispute between the
parties will not defeat an otherwise properly
supported motion for summary judgment.”
Id. at 247-48. Thus, the nonmoving party
may not rest upon mere conclusory
allegations or denials, but must set forth
“concrete particulars” showing that a trial is
needed. R.G. Grp., Inc. v. Horn & Hardart
Co., 751 F.2d 69, 77 (2d Cir. 1984) (quoting
SEC v. Research Automation Corp., 585 F.2d
31, 33 (2d Cir. 1978)). Accordingly, it is
insufficient for a party opposing summary
judgment “merely to assert a conclusion
without supplying supporting arguments or
facts.” BellSouth Telecomms., Inc. v. W.R.
Grace & Co., 77 F.3d 603, 615 (2d Cir. 1996)
(quoting Research Automation Corp., 585
F.2d at 33).

Court concludes that there are disputed issues
of material fact on the issue of whether
Chillemi’s guilty plea was knowing and
voluntary that preclude summary judgment
on this ground.
1. Preclusive Effect of a Guilty Plea on
Later Claims
In Cameron v. Fogarty, the Second
Circuit found that the common-law rule that
a plaintiff “can under no circumstances
recover if he was convicted of the offense for
which he was arrested” applied to bar § 1983
actions asserting false arrest. 806 F.2d 380,
387 (2d Cir. 1986) (citing Broughton v. State,
37 N.Y.2d 451, 458 (1975)). The Second
Circuit explained that, in such cases, courts
will accept the fact of the conviction as
“conclusive evidence of the good faith and
reasonableness of the officer’s belief” that
the arrest was lawful. Id. at 388. The Second
Circuit has also stated that this rule applies to
bar false arrest claims in cases where the prior
conviction resulted from a guilty plea,
Maietta v. Artuz, 84 F.3d 100, 102 n.1 (2d
Cir. 1996), and even in cases where the
defendant pleaded guilty to a lesser charge,
Timmins v. Toto, 91 F. App’x 165, 166 (2d
Cir. 2004); see also McNeill v. People of City
& State, No. 06-CV-4843 (NGG), 2006 WL
3050867, at *3 (E.D.N.Y. Oct. 24, 2006),
aff’d sub nom. McNeill v. People of City &
State of New York, 242 F. App’x 777 (2d Cir.
2007).

III. DISCUSSION
Defendants move for summary judgment
on all remaining causes of action.
Specifically, defendants argue that: (1)
Chillemi’s claims are precluded by his guilty
plea; (2) Chillemi cannot establish the
elements of his § 1983 claims for false arrest,
unlawful search incident to arrest, and
compelled self-incrimination; and (3)
Chillemi cannot show that the SHTPD or the
Town had a custom, policy, or practice that
led to his injury, as is required to establish
Monell liability against the Town.11
A. Effect of Chillemi’s Guilty Plea on
Claims in this Action

The Second Circuit has not, however,
addressed whether an involuntary guilty plea
would bar false arrest claims. Some district
courts have addressed this issue, finding that
the claims would not be barred. In Unger v.
Cohen, the court determined that an invalid
judgment of conviction would not serve to

Defendants argue that Chillemi’s guilty
plea precludes him from being able to assert
in this litigation that his arrest lacked
probable cause. As discussed below, the
11

The Court does not address Chillemi’s Equal
Protection claim because he abandoned it in his
opposition. (Pl.’s Mem. at 18.)
10

held that the guilty plea did not bar his claims
because the fact of a conviction is an
affirmative defense, and plaintiff was
claiming the guilty plea was involuntary. Id.
at 377-78. The Court noted that the question
of the voluntariness of Chillemi’s guilty plea
“is a matter for another day.” Id. at 378.
Finally, Judge Spatt similarly concluded that,
because Chillemi was contesting the
legitimacy of the guilty plea, “issues of
collateral estoppel cannot be determined at
this time.” Id. at 379.

bar false arrest claims. 718 F. Supp. 185, 187
(S.D.N.Y. 1989). The court pointed out that,
in establishing the general rule that plaintiffs
cannot recover for false arrest if they were
convicted, the Second Circuit in Cameron
cited the Restatement for the rule that a
“conviction . . . conclusively establishes the
existence of probable cause, unless the
conviction was obtained by fraud, perjury or
other corrupt means.” Id. (quoting Cameron,
806 F.2d at 387 (quoting Restatement
§ 667(1))). The Unger court, therefore,
found that a plaintiff could rebut the
“conviction defense”—that he or she had
been convicted as a bar against a false arrest
claim—by “establishing that the conviction
was invalid.” Id. at 187. The court explained
that, if a guilty plea is invalid it “thus does not
conclusively establish the existence of
probable cause for his arrest.” Id. at 188.

2. Validity of a Guilty Plea
Given the completion of discovery, the
Court now considers whether Chillemi has
submitted evidence that raises genuine
disputed issues of material fact as to the
validity of his guilty plea.
a. Legal Standard

These precise issues were raised by
defendants in a motion to dismiss in this case,
which was denied by Judge Spatt (before the
case was re-assigned to the undersigned). See
Chillemi v. Town of Southampton, 943 F.
Supp. 2d 365, 377 (E.D.N.Y. 2013) (citing
Unger, 718 F. Supp. at 187). In particular,
defendants argued: (1) that plaintiff was
barred from bringing the lawsuit based upon
the Supreme Court’s decision in Heck v.
Humphrey, 512 U.S. 477 (1994), because his
claims here would implicate the validity of
his underlying conviction; (2) plaintiff’s
claims were barred by his guilty plea, which
established probable cause for his arrest; and
(3) plaintiff was collaterally estopped from
challenging his arrest because he has pled
guilty and there has been no invalidation of
that conviction. Judge Spatt denied the
motion to dismiss on each of these grounds.
First, Judge Spatt held that an exception to
the Heck rule applied because plaintiff was
only assessed a fine and, given that he was
not “in custody,” had no ability to challenge
his arrest and conviction through habeas
corpus. Id. at 375-76. Second, Judge Spatt

The well-established standard for
determining the validity of a guilty plea is
“whether the plea represents a voluntary and
intelligent choice among the alternative
courses of action open to the defendant.” Hill
v. Lockhart, 474 U.S. 52, 56 (1985) (quoting
North Carolina v. Alford, 400 U.S. 25, 31
(1970)). The Supreme Court has held that,
under the Due Process Clause, a trial court
can only accept a guilty plea which is “done
voluntarily, knowingly, and intelligently,
‘with sufficient awareness of the relevant
circumstances and likely consequences.’”
United States v. Adams, 448 F.3d 492, 497
(2d Cir. 2006) (quoting Bradshaw v. Stumpf,
545 U.S. 175, 183 (2005)); accord Godinez
v. Moran, 509 U.S. 389, 400 (1993). Indeed,
a “plea of guilty entered by one fully aware
of the direct consequences of the plea is
voluntary in a constitutional sense unless
induced by threats, mis-representations, or
perhaps by promises that are by their nature
improper.” Bousley v. United States, 523
U.S. 614, 619 (1998) (internal alteration and
citations omitted).
11

or omission of counsel was unreasonable.”);
Williams v. United States, No. 07 CV 1804
RJD, 2012 WL 1116403, at *5 (E.D.N.Y.
Mar. 30, 2012) (“Actions and/or omissions
taken by counsel for strategic purposes
generally do not constitute ineffective
assistance of counsel.”) (citation omitted).
However, the Second Circuit has likened the
required showing at the summary judgment
stage to that required for a hearing on an
ineffective assistance of counsel claim, and
explained that “[t]o warrant a hearing on an
ineffective assistance of counsel claim, the
defendant need establish only that he has a
plausible claim of ineffective assistance of
counsel, not that he will necessarily succeed
on the claim.” Puglisi v. United States, 586
F.3d 209, 213 (2d Cir. 2009) (citation
omitted).

Normally, a guilty plea may not be
collaterally attacked because it constitutes an
admission as to all elements of the charged
crime. Salas v. United States, 139 F.3d 322,
324 (2d Cir. 1998). However, a defendant
may challenge a guilty plea on the ground
that it was not made knowingly and
voluntarily. United States v. Simmons, 164
F.3d 76, 79 (2d Cir. 1998).
In cases where a challenge to a guilty plea
is based on ineffective assistance of counsel,
the Supreme Court has held that the two-part
test set forth in in Strickland v. Washington,
466 U.S. 668 (1984), applies. Hill, 474 U.S.
at 58. The Court ruled that first, “the
defendant must show that counsel’s
representation fell below an objective
standard of reasonableness,” and second,
“[t]he defendant must show that there is a
reasonable probability that, but for counsel’s
unprofessional errors, the result of the
proceeding would have been different.” Id.
(quoting Strickland, 466 U.S. at 687-88,
694); see also id. at 56 (“Where . . . a
defendant is represented by counsel during
the plea process and enters his plea upon the
advice of counsel, the voluntariness of the
plea depends upon whether counsel’s advice
was within the range of competence
demanded of attorneys in criminal cases.”)
(citations omitted).

The second prong of this test, whereby
the defendant establishes the “prejudice” that
resulted from ineffective assistance of
counsel, Hill, 474 U.S. at 59, requires “some
objective evidence other than defendant’s
assertions” that counsel’s ineffective
assistance impacted the outcome of the
proceedings, Pham v. United States, 317 F.3d
178, 182 (2d Cir. 2003). Prima facie
evidence can include, for instance, evidence
of a “‘significant sentencing disparity’
between the sentence offered in the rejected
plea and the actual sentence imposed.”
Williams, 2012 WL 1116403, at *6 (quoting
Raysor v. United States, 647 F.3d 491, 495
(2d Cir. 2011)); see also Parafan-Homen v.
United States, No. 03-CV-5427 TCP, 2012
WL 4472262, at *13 (E.D.N.Y. Sept. 25,
2012).

In discussing the first prong of the
Strickland
test—demonstrating
that
“counsel’s representation fell below an
objective standard of reasonableness”—the
Supreme Court has stated that “[i]n applying
and defining this standard substantial
deference must be accorded to counsel’s
judgment.” Premo v. Moore, 562 U.S. 115,
126 (2001) (citing Strickland, 466 U.S. at
689) (emphasis added); see also Pratt v.
Greiner, 306 F.3d 1190, 1196 (2d Cir. 2002)
(“[I]t is all too easy for a court, examining
counsel’s defense after it has proved
unsuccessful, to conclude that a particular act

b. Analysis
Here, Chillemi contends that his plea was
involuntary because he believed that it was a
condition of his plea that he would be allowed
to return to the work release program and
that, if that understanding was erroneous, his
12

guilty. He had well-known, seasoned
criminal
defense
attorneys
representing him, and . . . struck a
“sweetheart” of a deal given his prior
history and the fact that he was on
work release at the time of his arrest.
. . . No person from the SHTPD was
present when Chillemi took the plea;
none of the defendant officers were
involved or influenced Chillemi’s
decision making regarding the plea.
Neither the Court nor any officer or
other official from the Town of
Southampton
made
any
representations to plaintiff about
plaintiff’s ability to participate in
work release following his July 8,
2009 arrest. . . . . Moreover, despite
counsel’s
attempt
to
rewrite
plaintiff’s
criminal
attorney’s
statements at the plea hearing, she
never indicated that Chillemi would
have the right to continue in work
release.

counsel was constitutionally ineffective in
advising him of that fact. (Pl.’s Mem. at 1116.) More specifically, Chillemi argues that
the record and transcript clearly show his plea
to have been involuntary:
The record and transcript is
completely devoid of any facts that
there were long periods of plea
negotiations,
that
[Chillemi]
understood the effect of a plea deal,
that he understood the effect of
uttering the word “guilty,” or that [he]
understood the statutory citations to
which he was pleading guilty. . . .
Neither the town justice nor the
prosecutor discussed the charges or
circumstances surrounding [the]
arrest. Additionally, the potential
negative consequences of his plea
agreement were not discussed during
the plea allocution.
[T]he plea
allocution that was provided was
sparse . . . . Th[e] affirmative
representation at the time of the plea
that Mr. Chillemi would be able to
return to the work release program
was false. Neither the court nor the
prosecutor or even his own attorney
for that matter advised Mr. Chillemi
of his right to a trial . . . . There is no
indication
that
Mr.
Chillemi
understood what his guilty plea meant
(or its future significance), what
rights he was waiving, or that he was
pleading guilty because he was, in
fact, guilty.

(Defs.’ Reply Mem. of Law in Supp. of Mot.
for Summary Judgment, ECF No. 85, at 5-6
(citing Tr. of Plea; Chillemi Tr. at 53)
(citations omitted).)
Having carefully reviewed the record, the
Court concludes that there are disputed issues
of fact that preclude summary judgment on
whether Chillemi’s guilty plea was knowing
and voluntary. As noted supra, the transcript
shows that, during the plea, Chillemi’s
attorney (Mr. Ghanayem) made explicit
reference to Chillemi’s return to work
release, after which the prosecutor confirmed
the statement:

(Pl.’s Mem. at 13-15 (citing Tr. of Plea)
(citations omitted).)

Mr. Ghanayem: And Your Honor, I
would also like to put on the record
that this is a generous disposition and
it gives my client -- to maintain a
work release program, which he has
been doing very well in. We have

Defendants, on the other hand, counter
that Chillemi’s plea was not involuntary:
This was not a first time offender,
confused by the legal system,
pleading guilty within hours of his
arrest. . . . He had previously pled
13

At my plea allocution on October 29,
2009 before the Honorable Edward
D. Burke, I had only one concern: to
return to the work-release program.
. . . During my plea allocution, I did
not admit factual guilt. I only pled
guilty to certain statutory citations:
221.05 and 511.0A. During my plea
allocution, I only accepted the plea
agreement on the false premise that I
would be able to return to work
release.
Had the town justice,
prosecutor, or my own attorney told
me that a guilty plea would mean that
I would be removed from the work
release program and placed back into
incarceration, I never would have
pleaded guilty.

talked about this with his family and
he is very anxious to get back to that.
. . . I just wanted to make sure that I
recorded that.
Mr. Mashhadian: That’s correct.
(Tr. of Plea at 4.) The Court notes that there
is a key word missing in the statement: “it
gives my client -- to maintain a work release
program.” It is unclear whether this was a
transcription error or a lack of clarity by the
lawyer.
Although plaintiff’s counsel
suggests that it means Chillemi had the
“right” to remain in a work release program
under the plea disposition, the Court
concludes that the transcript is ambiguous.
However, construing the ambiguity in the
transcript most favorably to plaintiff, one
could conclude that remaining in the work
release program was a condition of the plea
and that it was confirmed by the prosecutor
on the record. Although that is not the only
inference that could be drawn from the
ambiguity, it is certainly one reasonable
inference that could be drawn. Moreover,
although defendants suggested that the
prosecutor would have no ability to bind a
separate agency with respect to the
continuation of work release, that lack of
authority would not render the plea voluntary
if, for whatever reason, it was made a
condition of the plea and that condition was
not fulfilled.

(Chillemi Decl. ¶¶ 19-22.) Chillemi’s sworn
statement is sufficient to create an issue of
disputed fact as to whether his plea was
involuntary due to ineffective assistance of
counsel. In other words, construing the
evidence most favorably to Chillemi, he may
be able to satisfy both prongs of the Hill
standard—the plea was invalid because (1)
his counsel’s advice fell below the “range of
competence” demanded of him, and (2) there
was a “reasonable probability that [Chillemi]
would not have pleaded guilty” were it not for
his counsel’s deficient conduct. (Pl.’s Mem.
at 12.) Moreover, any mistaken belief that he
would return to the work release program
would also go to the determination of
whether his plea was “knowing,” and done
“with sufficient awareness of the relevant
circumstances and likely consequences.”
Adams, 448 F.3d at 497.

Chillemi also asserts that, apart from
whether remaining in work release was a
condition of the plea that was placed on the
record, his plea was involuntary because it
was his clear understanding, based upon the
advice of his attorney, that his work release
would not be revoked because of his guilty
plea. Chillemi further states under oath that
he would have never pleaded guilty if he
knew it could have resulted in his removal
from work release. Specifically, in his
declaration, Chillemi explains:

In sum, given the ambiguities in the
record, and viewing the facts in the light most
favorable to Chillemi, the Court concludes
that there is a genuine dispute as to material
facts that precludes summary judgment on
the question of whether Chillemi’s guilty
plea was knowing and voluntary.
14

Accordingly, summary judgment on this
ground is denied.

probable cause serves as a complete defense
to a false arrest claim. As discussed below,
genuine disputes of material fact exist as to
whether Sickles in fact had probable cause to
make the arrest, and preclude summary
judgment on this claim.

B. Section 1983 Claims
All of Chillemi’s surviving claims in this
action were brought pursuant to 42 U.S.C.
§ 1983 (“Section 1983” or “§ 1983”).
Defendants claim that the Court should grant
summary judgment on the following
grounds: (1) Chillemi failed to establish the
necessary elements of his § 1983 claims; (2)
these claims fail as to individual defendants
Kiernan and Tully because Chillemi did not
establish their personal involvement; (3)
defendants are entitled to qualified immunity;
and (4) Chillemi failed to establish Monell
liability against the Town. The Court will
address each argument in turn.

Under § 1983, a false arrest claim derives
from the Fourth Amendment’s prohibition
against unreasonable searches and seizures.
Jaegly v. Couch, 439 F.3d 149, 151 (2d Cir.
2006); see also Jocks v. Tavernier, 316 F.3d
128, 134 (2d Cir. 2003) (citing Weyant, 101
F.3d at 852) (“Claims for false arrest . . .
brought under § 1983 to vindicate the Fourth
and Fourteenth Amendment right to be free
from
unreasonable
seizures,
are
‘substantially the same’ as claims for false
arrest . . . under state law.”).

1. Elements of Chillemi’s § 1983 Claims

In order to prevail on a false arrest claim,
Chillemi needs to prove the following four
elements: “(1) the defendant intended to
confine [the plaintiff], (2) the plaintiff was
conscious of the confinement, (3) the plaintiff
did not consent to the confinement and (4) the
confinement was not otherwise privileged.”
Jocks, 316 F.3d at 134-35 (quoting
Broughton, 37 N.Y.2d at 456). The fourth
element is the only one in dispute for
purposes of the motion.

To prevail on a claim under § 1983, a
plaintiff must show: (1) the deprivation of
any rights, privileges, or immunities secured
by the Constitution and its laws, (2) by a
person acting under the color of state law. 42
U.S.C. § 1983. Section 1983 does not itself
create substantive rights; it offers “a method
for vindicating federal rights elsewhere
conferred.” Patterson v. County of Oneida,
375 F.3d 206, 225 (2d Cir. 2004) (citation
omitted). Chillemi brings claims under
§ 1983 for violations of the Fourth, Fifth, and
Fourteenth Amendments.

Probable cause is a complete defense to a
false arrest claim. See Heller v. Bedford
Cent. Sch. Dist., 144 F. Supp. 3d 596, 622
(S.D.N.Y. 2015) (collecting cases). “The
same holds true for [a] false imprisonment
claim[] because, under New York law, the
claim is identical to a false arrest claim and
the federal claim looks to the elements of the
state claim.” Killburn v. Village of Saranac
Lake, 413 F. App’x 362, 363 (2d Cir. 2011)

a. False Arrest/False Imprisonment Claims
Defendants move for summary judgment
on Chillemi’s false arrest/false imprisonment
claims12 on the grounds that Chillemi’s
confinement was privileged because Sickles
had probable cause to arrest him, and that
12

The Court focuses its discussion on the false arrest
claim because, under New York law, “the tort of false
arrest is synonymous with that of false imprisonment,”
and courts use that tort to analyze an alleged Fourth
Amendment violation in the § 1983 context. Posr v.

Doherty, 944 F.2d 91, 96 (2d Cir. 1991); see also
Singer v. Fulton Cty. Sheriff, 63 F.3d 110, 118 (2d Cir.
1995).

15

of law that probable cause existed where a
“sparse factual record . . . [did] not eliminate
the possibility that the defendants initiated
the criminal proceeding without probable
cause.” Rounseville v. Zahl, 13 F.3d 625, 630
(2d Cir. 1994). Where a plaintiff “pointed to
facts from which a jury could find an absence
of probable cause for the . . . arrest,” courts in
this circuit have found those facts to be
sufficient to create a genuine dispute of
material fact. Sassower v. City of White
Plains, County of Westchester, No. 89 CIV.
1267 (MJL), 1995 WL 222206, at *5
(S.D.N.Y. Apr. 13, 1995) (discussing
plaintiff’s affidavit denying that she had
yelled or sworn at defendant police officers,
as they claimed in supporting their arrest for
disorderly conduct).

(citations omitted). However, the burden of
proving this affirmative defense lies with the
defendant because “when an arrest is made
without a warrant, the officer has acted
outside the scope of the legal process and
therefore a rebuttable presumption arises that
such an arrest is unlawful.” Rodriguez v. City
of New York, 563 N.Y.S.2d 1004, 1005 (N.Y.
Sup. Ct. 1990) (citing Broughton, 37 N.Y.2d
at 458).
In general, probable cause is established
where “the [arresting] officer has ‘knowledge
of, or reasonably trustworthy information as
to, facts and circumstances that are sufficient
to warrant a person of reasonable caution in
the belief that an offense has been or is being
committed by the person to be arrested.’”
Finigan v. Marshall, 574 F.3d 57, 62 (2d Cir.
2009) (quoting Zellner v. Summerlin, 494
F.3d 344, 368 (2d Cir. 2007)); see also
Weyant, 101 F.3d at 852 (citing Dunaway v.
New York, 442 U.S. 200, 208 n.9 (1979)
(additional citations omitted)). Furthermore,
the propriety of an arrest does not depend on
whether the suspect was ultimately found
guilty, but, rather, on the existence of
probable cause at the time of the arrest. See
Haussman v. Fergus, 894 F. Supp. 142, 147
(S.D.N.Y. 1995) (citing Pierson v. Ray, 386
U.S. 547, 555 (1967)); see also Anderson v.
Creighton, 483 U.S. 635, 641 (1987).

Sickles arrested Chillemi on July 8, 2009,
for aggravated unlicensed operation of a
motor vehicle and possession of a controlled
substance. Sickles claims, among other
things, that (1) he observed Chillemi driving
the car, with Tara as a passenger, and (2) after
he placed Chillemi under arrest for
aggravated unlicensed operation of a motor
vehicle, he searched Chillemi and found a
bag of cocaine in his pocket. (Defs.’ Mem.,
Ex. E (“Sickles Tr.”) at 22-23, 31-32.)
However, Chillemi has submitted sworn
statements that (1) Tara was driving the car,
and he was just a passenger, and (2) he did
not have any drugs in his possession.
(Chillemi Decl. ¶¶ 13, 15, 26.) Tara also has
testified that she was driving the vehicle on
July 8, 2009, not Chillemi. (Tara Tully Tr. at
45.)

At the summary judgment stage, “[t]he
question of whether or not probable cause
existed may be determinable as a matter of
law if there is no dispute as to the pertinent
events and the knowledge of the officers, or
may require a trial if the facts are in dispute.”
Weyant, 101 F.3d at 852 (citations omitted).
Where an issue of probable cause is “factual
in nature,” it must be presented to a jury.
Moore v. Comesanas, 32 F.3d 670, 673 (2d
Cir. 1994) (citations omitted).

These disputed issues of fact clearly
preclude summary judgment on the question
of whether there was probable cause for the
arrest. If Chillemi’s version of the events is
credited—namely, that he was not driving
and did not have cocaine on him—Sickles

The Second Circuit has indicated that a
district court should not conclude as a matter
16

clearly would not have had probable cause
for the arrest.13

2006). “This process allows officers to draw
on their own experience and specialized
training to make inferences from and
deductions about the cumulative information
available to them that ‘might well elude an
untrained person.’” United States v. Arvizu,
534 U.S. 266, 273 (2002) (quoting United
States v. Cortez, 449 U.S. 411, 418 (1981)).
Like probable cause, whether “reasonable
suspicion exists is an objective inquiry; the
‘actual motivations of the individual officers
involved’ in the stop ‘play no role’ in the
analysis.” Holeman v. City of New London,
425 F.3d 184, 190 (2d Cir. 2005) (quoting
Whren v. United States, 517 U.S. 806, 813
(1996)).

Accordingly, summary judgment on the
false arrest claim is denied.
b. Other Fourth Amendment Claims
Chillemi’s other Fourth Amendmentbased § 1983 claims are that (1) there was no
basis to stop him and search him at the house,
and (2) Sickles fabricated evidence against
him.14
With respect to the unreasonable stop and
search claim, in general, “[t]he police can
stop and briefly detain a person for
investigative purposes if the officer has a
reasonable suspicion supported by articulable
facts that criminal activity ‘may be afoot,’
even if the officer lacks probable cause.”
United States v. Sokolow, 490 U.S. 1, 7
(1989) (quoting Terry v. Ohio, 392 U.S. 1, 30
(1968)). In examining whether an officer had
reasonable suspicion at the time of the stop,
courts “assess the totality of the
circumstances supporting the investigatory
stop . . . to decide whether the officer’s
suspicion of wrongdoing has an objective and
particularized basis.”
United States v.
Muhammad, 463 F.3d 115, 121 (2d Cir.

This Fourth Amendment claim is
premised on the same evidence that plaintiff
uses to support his false arrest claim: namely,
that Sickles lacked any basis for the initial
stop because plaintiff was not driving the car
and, thus, there also was no basis for the
search incident to arrest. Thus, if plaintiff’s
version of the events is accepted by the jury,
Sickles would not have had the required
“reasonable suspicion” to stop Chillemi, and
no legal basis to search him. Accordingly, in
light of the parties’ genuine dispute as to
material facts regarding the circumstances

13

As noted supra, Chillemi also asserts that there was
no probable cause for the arrest because he had a valid
license at the time of the arrest. Defendants have
submitted evidence to rebut Chillemi’s contention on
this issue. In particular, in addition to Sickles’s
testimony that Chillemi’s license was suspended,
defendants have offered the New York State Police
Information Network (“NYSPIN”) report containing
Chillemi’s criminal record as an exhibit to their
motion for summary judgment, showing that
Chillemi’s license was suspended when the report was
run on the date of Chillemi’s arrest. (NYSID Report
at 2.) In any event, the resolution of this factual issue
in defendants’ favor would not be dispositive on the
question of probable cause for the arrest. In other
words, even assuming Chillemi’s license was
suspended, Sickles would not have had probable cause
to arrest Chillemi for unlicensed operation of the
vehicle if (as Chillemi claims) Sickles fabricated the

fact that he observed Chillemi driving the vehicle, and
Chillemi was not driving at all.
14

In their motion for summary judgment briefing,
defendants do not specifically address the claim that
Sickles fabricated evidence by producing the bag of
cocaine that he claimed to find in Chillemi’s pocket.
Defendants do, however, move for summary judgment
on the “illegal search and seizure claim[].” (Defs.’
Mem. at 15). Defendants argue that the search
incident to arrest was lawful and that, regardless, the
remedy for an unlawful search or seizure would be
suppression of evidence at trial, rather than recovery
through a § 1983 action. (Id. at 16.) The Court will
treat defendants’ arguments relating to the illegal
search as also encompassing Officer Sickles’s
purported fabrication of evidence.

17

surrounding the arrest, the Court also denies
summary judgment on Chillemi’s claim for
unreasonable search and seizure based upon
the stop and search.

requirement for a § 1983 action: that the
alleged misconduct in fact resulted in the
deprivation of liberty at issue. Zahrey, 221
F.3d at 350 (explaining that, even where a
government actor’s misconduct has been
established, “no deprivation of liberty occurs
unless and until the jury convicts and the
defendant is sentenced”).

With respect to Chillemi’s § 1983 claim
for fabrication of evidence, the Second
Circuit has ruled that there is a “right not to
be deprived of liberty as a result of the
fabrication of evidence by a government
officer acting in an investigating capacity,”
and that the violation of that right is
actionable under § 1983. Zahrey v. Coffey,
221 F.3d 342, 349, 357 (2d Cir. 2000). The
Second Circuit requires that, to succeed on
such claims, it must be “reasonably
foreseeable that the false evidence will be
used to deprive the defendant of liberty.” Id.
at 357.

As the Court concluded with respect to
the other Fourth Amendment claims, there is
a genuine dispute of material facts as to
whether Sickles fabricated evidence that led
to Chillemi’s deprivation of liberty.15 The
Court, therefore, denies summary judgment
as to this claim.
c. Compelled Self-Incrimination Claim
Chillemi claims that his Fifth
Amendment right to freedom from compelled
self-incrimination was violated. (Compl.
¶ 1.) In his opposition to summary judgment,
however, Chillemi explains that his rights
were violated because he “never made the
statements that are currently being used
against him.”
(Pl.’s Mem. at 19-20.)
Chillemi clarifies that he has not alleged that
his Fifth Amendment right was violated
through coercion or torture. (Id. at 19.)
Given that Chillemi does not allege that he
made any statements to the police, he cannot
possibly assert
a compelled
selfincrimination claim; rather, as noted supra,
his allegations regarding the fabricated selfincriminating statements are properly
brought under the Fourth Amendment.
Accordingly, summary judgment is granted
in defendants’ favor on the compelled selfincrimination claim.

Chillemi claims that Sickles feigned
finding a bag of cocaine in his pocket during
the search incident to arrest, and that Sickles
himself produced the bag. (Pl.’s 56.1 ¶ 62.)
In Zahrey, the Second Circuit provides
examples of alleged misconduct that were
found to have deprived § 1983 plaintiffs of
their liberty, such as when “a prosecutor
places in evidence testimony known to be
perjured” and the accused is then convicted
and sentenced. 221 F.3d at 350. Chillemi
alleges similar misconduct: he claims that
Sickles included information in his
Misdemeanor Information about having
found a bag of cocaine that Sickles knew to
be false (because he fabricated the story). As
noted, Chillemi also contends that Sickles
fabricated that he observed Chillemi driving
a vehicle without a license, and that Chillemi
made incriminating post-arrest statements.
Chillemi was then convicted and sentenced
for the charges that resulted from Sickles’s
arrest. If plaintiff’s evidence is credited, this
claim could be found to satisfy the causation

2. Liability of Kiernan and Tully
Chillemi brings his § 1983 claims against
defendants Kiernan and Tully based on their

15

Chillemi also asserts Fourth Amendment claims
against defendants Tully and Kiernan. The issues

concerning their alleged personal involvement are
discussed infra.
18

that sanctioned conduct amounting to a
constitutional violation, or allowing such a
policy or custom to continue, (4) grossly
negligent supervision of subordinates who
committed a violation, or (5) failure to act on
information indicating that unconstitutional
acts were occurring.” Id. at 145 (citations
omitted).

supervisory liability and failure to intercede.
Chillemi alleges that defendants Kiernan and
Tully had supervisory power over Sickles,
(Compl. ¶¶ 12, 14, 88), and knew Officer
Sickles’s statements in the General Traffic
Complaint and Misdemeanor Information
against Chillemi were incorrect, (id. ¶¶ 3233). Further, Chillemi’s allegations suggest
that the motive behind the arrest was all three
“defendants’ disapproval of [Chillemi’s]
romantic relationship with Defendant Tully’s
daughter.” (Defs.’ 56.1 ¶ 99.)

With respect to Kiernan, plaintiff has set
forth several pieces of evidence to support his
claim that Kiernan was personally involved
in the alleged constitutional violations in this
case. First, there is evidence that Kiernan
arrived at the scene shortly after Chillemi’s
arrest by Sickles. Second, Chillemi asserts
that Kiernan fabricated statements by
Chillemi at the scene in an effort to support
the false arrest. Third, Kiernan administered
the oath for the General Traffic Complaint
and Misdemeanor Information signed by
Sickles on July 8, 2009. As to Kiernan’s
knowledge of the allegedly unconstitutional
nature of Sickles’s search and arrest, in
addition to the alleged fabrication of
statements by Kiernan, plaintiff points to
involvement of both Sickles and Kiernan in
his 2007 arrest and the circumstances
surrounding that encounter, as well as the fact
that Tara told Chillemi that Kiernan is her
godfather. In other words, Chillemi asserts
that the totality of the evidence demonstrates
that Kiernan knew that Sickles had a vendetta
against Chillemi because of Chillemi’s
relationship with Tara and that Sickles was
intent upon fabricating evidence to support
an arrest against Chillemi. Thus, Chillemi
contends that Kiernan is liable based upon his
alleged grossly negligent failure to supervise
Sickles and/or intercede to stop Sickles’s
unconstitutional acts once he arrived at the
scene. The Court concludes that, construing
the evidence most favorably to plaintiff,
plaintiff has raised genuine issues of material
fact as to (1) whether Kiernan was aware that
Sickles was fabricating evidence against
Chillemi on July 8, 2009, (2) whether

Defendants claim that Kiernan and Tully
should not be held liable for the alleged
misconduct because Chillemi failed to
establish their personal involvement, as is
required to bring these § 1983 claims against
them on the basis of their supervisory
liability. (Defs.’ Mem. at 17-18.) As
discussed below, the Court concludes that
there is sufficient evidence of personal
involvement with respect to Kiernan that
preclude summary judgment with respect to
the Fourth Amendment claims against him.
However, given the lack of any evidence of
Tully’s personal involvement in the arrest or
the alleged fabrication of evidence, summary
judgment is warranted in his favor on all
claims.
“It is well settled in this Circuit that
personal involvement of defendants in
alleged constitutional deprivations is a
prerequisite to an award of damages under
§ 1983.” Wright v. Smith, 21 F.3d 496, 501
(2d Cir. 1994) (citations omitted). In other
words, “supervisor liability in a § 1983 action
depends on a showing of some personal
responsibility, and cannot rest on respondeat
superior.” Hernandez v. Keane, 341 F.3d
137, 144 (2d Cir. 2003). Supervisor liability
can be shown in one or more of the following
ways: “(1) actual direct participation in the
constitutional violation, (2) failure to remedy
a wrong after being informed through a report
or appeal, (3) creation of a policy or custom
19

judgment on qualified immunity grounds is
unwarranted given the disputed issues of fact
in the record as to whether Sickles and
Kiernan were involved in the intentional
fabrication of evidence to support Chillemi’s
arrest in July 2009.

Kiernan himself fabricated incriminating
statements by Chillemi on that date, and (3)
whether Kiernan was grossly negligent in his
supervision of Sickles and/or had an
opportunity to intercede to prevent the false
arrest and detention once he arrived at the
scene on July 8, 2009.
Accordingly,
summary judgment is denied as to Kiernan on
the Fourth Amendment claims.

The Supreme Court recently affirmed that
“[q]ualified immunity attaches when an
official’s conduct ‘does not violate clearly
established statutory or constitutional rights
of which a reasonable person would have
known.’” White v. Pauly, 137 S. Ct. 548, 551
(2017) (per curiam) (quoting Mullenix v.
Luna, 136 S. Ct. 305, 308 (2015) (per
curiam)). The Second Circuit has held that “a
right is clearly established if (1) the law is
defined with reasonable clarity, (2) the
Supreme Court or the Second Circuit has
recognized the right, and (3) a reasonable
defendant would have understood from the
existing law that his conduct was unlawful.”
Luna v. Pico, 356 F.3d 481, 490 (2d Cir.
2004) (quoting Anderson v. Recore, 317 F.3d
194, 197 (2d Cir. 2003)); see also
McCullough v. Wyandanch Union Free Sch.
Dist., 187 F.3d 272, 278 (2d Cir. 1999).
Defendants claim that it was objectively
reasonable for Sickles to believe that he acted
lawfully in stopping, searching, and arresting
Chillemi, and that Kiernan acted in an
objectively reasonable manner in signing off
on his arrest.

With respect to Tully, defendants have
submitted evidence that Tully (1) had no
involvement in the investigation of Chillemi,
(2) was not present at either the 2007 arrest
or 2009 arrest, (3) never interacted with or
met Chillemi, and (4) never had any
conversations with Sickles or Kiernan about
Chillemi.
Plaintiff has submitted no
admissible
evidence
to
controvert
defendants’ submissions. Instead, plaintiff
simply speculates that, because Chillemi’s
relationship with Tully’s estranged daughter
was the purported motivation of the
unconstitutional conduct by Sickles, Tully
must have had some unknown involvement.
Such sheer speculation, however, does not
create a genuine dispute as to material facts
that precludes summary judgment. Even
construing the evidence most favorably to
Chillemi, no rational juror could find that
Tully participated in (or was even aware of)
the purported constitutional violations by
Sickles. Accordingly, Tully is entitled to
summary judgment on all claims.
3.

The Second Circuit has held that courts
should cloak defendants with qualified
immunity at the summary judgment stage
“only ‘if the court finds that the asserted
rights were not clearly established, or if the
evidence is such that, even when it is viewed
in the light most favorable to the plaintiff[]
and with all permissible inferences drawn in
[his] favor, no rational jury could fail to
conclude that it was objectively reasonable
for the defendants to believe that they were
acting in a fashion that did not violate a
clearly established right.’”
Ford v.

Qualified Immunity

All three individual defendants also argue
that they are entitled to qualified immunity.
As a threshold matter, the Court has
concluded that Tully is entitled to summary
judgment on all claims because of the lack of
any evidence of his personal involvement.
Thus, the Court need not address the
qualified immunity issue as it relates to Tully.
With respect to defendants Sickles and
Kiernan, the Court concludes that summary
20

In arguing that they are entitled to
qualified immunity, defendants do not
contest the existence of a constitutional right;
rather, they argue that reasonable people
would disagree about the constitutionality of
their actions. However, as discussed supra,
viewing the evidence most favorably to
plaintiff, including drawing all reasonable
inferences in his favor, Chillemi has created
a material issue of fact as to whether
defendants Sickles and Kiernan participated
in the fabrication of evidence to establish
probable cause to arrest Chillemi. Under the
circumstances of this case, these disputed
issues of fact also preclude summary
judgment on the issue of qualified immunity.
In particular, if Chillemi’s sworn version of
the facts is accepted by the jury—namely,
that Sickles had decided to pursue the car
even though he had seen Tara (not Chillemi)
driving, and that he fabricated the fact that he
had found cocaine on Chillemi—Sickles
clearly would lack even arguable probable
cause, and no reasonable officers would
disagree on the constitutionality of such
conduct. Similarly, if Chillemi proves that
Kiernan was aware of Sickles’s fabrication of
evidence at the scene of the arrest and failed
to intervene in Sickles’s decision to detain
Chillemi, Kiernan also would not be
protected by qualified immunity.

McGinnis, 352 F.3d 582, 597 (2d Cir. 2003)
(quoting Williams v. Greifinger, 97 F.3d 699,
703 (2d Cir. 1996)); see also Oliveira v.
Mayer, 23 F.3d 642, 649 (2d Cir. 1994)
(“Though [qualified] immunity ordinarily
should be decided by the court, that is true
only in those cases where the facts
concerning the availability of the defense are
undisputed; otherwise, jury consideration is
normally required.”) (citations omitted).
Defendants argue that, even if Sickles
lacked probable cause, he is entitled to
qualified immunity. (Defs.’ Mem. at 21.)
Even without probable cause, a police officer
is entitled to qualified immunity “so long as
‘arguable probable cause’ was present when
the arrest was made.” Figueroa v. Mazza,
825 F.3d 89, 100 (2d Cir. 2016) (quoting
Zalaski v. City of Hartford, 723 F.3d 382, 390
(2d Cir. 2013)). “A police officer has
arguable probable cause ‘if either (a) it was
objectively reasonable for the officer to
believe that probable cause existed, or (b)
officers of reasonable competence could
disagree on whether the probable cause test
was met.’” Id.
The Second Circuit has affirmed that
“‘[a]rguable’ probable cause should not be
misunderstood to mean ‘almost’ probable
cause. . . . If officers of reasonable
competence would have to agree that the
information possessed by the officer at the
time of arrest did not add up to probable
cause, the fact that it came close does not
immunize the officer.” Jenkins v. City of New
York, 478 F.3d 76, 87 (2d Cir. 2007). Under
this standard, an arresting officer is entitled
to qualified immunity, as a matter of law,
only “if the undisputed facts and all
permissible inferences favorable to the
plaintiff show . . . that officers of reasonable
competence could disagree on whether the
probable cause test was met.” McClellan v.
Smith, 439 F.3d 137, 147-48 (2d Cir. 2006)
(citations omitted).

This conclusion is consistent with wellsettled Second Circuit precedent.
For
example, in Ricciuti v. N.Y.C. Transit Auth.,
124 F.3d 123 (2d Cir. 1997), the Second
Circuit held that the district court erred in
granting summary judgment in favor of the
police officers on qualified immunity
grounds with respect to the alleged
fabrication of evidence. Id. at 130. The
Court found qualified immunity unavailable
because conspiring to fabricate and forward
to prosecutors a known false confession
“violates an accused’s clearly established
constitutional right, and no reasonably
competent police officer could believe
21

otherwise.” Id.; see also McSherry v. City of
Long Beach, 423 F.3d 1015, 1022 (9th Cir.
2005) (reversing grant of judgment as a
matter of law on qualified immunity grounds
where plaintiff “raised a disputed issue of fact
as to whether defendants fabricated some of
the evidence used to obtain [plaintiff’s]
conviction”); Kingsland v. City of Miami,
382 F.3d 1220, 1233 (11th Cir. 2004)
(reversing summary judgment on qualified
immunity grounds and noting that “because a
jury question exists as to whether the
defendants constructed evidence upon which
to base [plaintiff’s] arrest, the question
whether arguable probable cause for the
arrest existed is aptly suited for a jury”).
Similarly, in Jenkins, the Second Circuit
found that some of the facts alleged to
provide a basis for probable cause were
“vigorously disputed,” including facts that
were “clearly material” to the district court’s
finding of arguable probable cause. 478 F.3d
at 89. The Second Circuit, therefore, found
that the district court had erred in part in
granting summary judgment. Id. at 91.

defendants argue that municipal action
directed at one individual does not qualify as
a policy, custom, or practice. (Id. at 13-14.)
As set forth below, the Court concludes that
there are issues of fact that preclude summary
judgment on the Monell claim against the
Town with respect to Chillemi’s Fourth
Amendment claims.16
A municipal entity may be held liable
under § 1983 where the plaintiff
demonstrates that the constitutional violation
complained of was caused by a municipal
“policy or custom.” Monell v. Dep’t of Social
Services of City of New York, 436 U.S. 658,
694 (1978) (emphasizing that the municipal
policy must be the “moving force of the
constitutional violation”). “The policy or
custom need not be memorialized in a
specific rule or regulation.” Kern v. City of
Rochester, 93 F.3d 38, 44 (2d Cir. 1996)
(citing Sorlucco v. N.Y.C. Police Dep’t, 971
F.2d 864, 870 (2d Cir. 1992)). Instead,
constitutional violations by government
officials that are “persistent and widespread”
can be “so permanent and well settled as to
constitute a custom or usage with the force of
law, and thereby generate municipal
liability.” Sorlucco, 971 F.2d at 870-71
(quoting Monell, 436 U.S. at 691) (citation
omitted). In addition, “[t]he failure to train or
supervise [municipal] employees may
constitute an official policy or custom if the
failure amounts to ‘deliberate indifference’ to
the rights of those with whom the [municipal]
employees interact.” Wray v. City of New
York, 490 F.3d 189, 195 (2d Cir. 2007)
(quoting City of Canton v. Harris, 489 U.S.
378, 388 (1989)). Deliberate indifference
exists when the plaintiff establishes that (1)
“a policymaker knows ‘to a moral certainty’

Accordingly, given the disputed issues of
fact in the record regarding the alleged
fabrication of evidence by Sickles and
Kiernan to support Chillemi’s arrest, the
motion for summary judgment on qualified
immunity grounds is denied.
4. The Town’s Liability
Defendants request that the Court grant
summary judgment on the Monell claim
against the Town on the grounds that
“Chillemi has not articulated a [Town] policy
or practice” that led to the deprivation of his
rights. (Defs.’ Mem. at 12.) Further,
16

As noted above, Chillemi’s remaining § 1983 claims
are for false arrest/imprisonment, unreasonable search
and seizure, and fabrication of evidence. Thus, the
Court need not address the Town’s liability under
Monell with respect to Chillemi’s compelled selfincrimination claim. See Segal v. City of New York,

459 F.3d 207, 219 (2d Cir. 2006) (“Because the district
court properly found no underlying constitutional
violation, its decision not to address the municipal
defendants’ liability under Monell was entirely
correct.”).
22

that [municipal] employees will confront a
particular situation”; (2) “the situation either
presents the employee with ‘a difficult choice
of the sort that training or supervision will
make less difficult,’ or ‘there is a history of
employees mishandling the situation’”; and
(3) “the wrong choice by the [municipal]
employee will frequently cause the
deprivation of a citizen’s constitutional
rights.” Id. at 195-96 (quoting Walker v. City
of New York, 974 F.2d 293, 297-98 (2d Cir.
1992)). The Supreme Court has reiterated
that “[a] pattern of similar constitutional
violations by untrained employees is
‘ordinarily necessary’ to demonstrate
deliberate indifference for purposes of failure
to train.” Connick v. Thompson, 563 U.S. 51,
62 (2011) (quoting Bd. of Cty. Comm’rs of
Bryan Cty., Okla. v. Brown, 520 U.S. 397,
409 (1997)). However, “in a narrow range of
circumstances”
where
unconstitutional
actions are the obvious consequence of a
failure to train, “a pattern of similar
violations might not be necessary to show
deliberate indifference.” Id. at 63 (quoting
Bd. of Cty. Comm’rs of Bryan Cty., 520 U.S.
at 409). Moreover, a single action also can
“provide[] a basis for municipal liability
where it is taken by, or is attributable to, one
of the city’s authorized policymakers.”
Amnesty Am., 361 F.3d at 126. In order to be
deemed a “policymaker” or “decisionmaker,”
an official must “possess[] final authority to
establish municipal policy with respect to the
Pembaur v. City of
action ordered.”
Cincinnati, 475 U.S. 469, 481 (1986). It is
important to emphasize that a municipal
entity may be held liable only where the

entity itself commits a wrong; “a
municipality cannot be held liable under
§ 1983 on a respondeat superior theory.”
Monell, 436 U.S. at 691; see also Segal v.
City of New York, 459 F.3d 207, 219 (2d Cir.
2006) (“Monell does not provide a separate
cause of action for the failure by the
government to train its employees; it extends
liability to a municipal organization where
that organization’s failure to train, or the
policies or customs that it has sanctioned, led
to an independent constitutional violation.”).

17

fallen asleep at their kitchen table with his duty gun in
hand prior, and that she felt she and her children were
in danger. Upon receiving this complaint Lieutenant
Kiernan failed to take decisive action for over 18 hours
and permitted Police Officer Sickles to work full duty
for the remainder of his 4 x 12 tour that date.
Lieutenant James Kiernan’s conduct constitutes
incompetence.” (Chillemi Decl., Ex. 7 at 3.)

As a threshold matter, it is unclear from
the record whether Kiernan, as the
supervisory sergeant of the Town’s SCU in
2009, would qualify as an authorized
policymaker, in terms of establishing certain
policies governing his unit’s arrests, which
could form the basis for a Monell claim in
connection with the 2009 arrest. In any
event, plaintiff has put forth evidence that
creates a genuine issue of disputed fact as to
whether there was a failure to supervise
Sickles
that
caused
the
alleged
unconstitutional violations in this case with
respect the July 8, 2009 arrest. First, with
respect to the failure to supervise, plaintiff
points to the circumstances surrounding the
arrest itself and his observation that Kiernan,
upon arriving at the scene, not only failed to
supervise Sickles, but also fabricated
statements by plaintiff that would support the
unlawful arrest. Second, the Court notes that
Kiernan pled guilty to, inter alia, multiple
charges (Charge 4, Charge 10, Charge 11)
that relate to his supervision of Sickles and
Kiernan’s competence.17
(See Chillemi

Charge Four alleged: “Lieutenant James Kiernan
violated Southampton Town Police Department Rules
and Regulations, Article VIII, Rules of Conduct, Rule
9 on or about October 25, 2011, when Lieutenant
James Kiernan received a call for help by Police
Officer Sickles’s wife, Erica Sickles, stating that her
husband was suffering from the side effects of several
prescribed medications that he was taking, that he was
unable to drive a car without falling asleep, that he had
23