The Clown

Case 16-3932, Document 66, 06/12/2017, 2055620, Page1 of 56
16-3932
United States Court of Appeals
for the Second Circuit
FRANCESCO PORTELOS,
Plaintiff-Appellant,
against
LINDA HILL, Principal of I.S. 49, in her official and

individual capacity, ERMINIA CLAUDIO, CITY OF NEW YORK,
CITY OF NEW YORK DEPARTMENT OF EDUCATION,
Defendants-Appellees.
DENNIS WALCOTT, Chancellor of New York City

Department of Education,
Defendant.
On Appeal from the United States District Court

for the Eastern District of New York
BRIEF FOR APPELLEES
ZACHARY W. CARTER
Corporation Counsel
of the City of New York
Attorney for Appellees
SCOTT SHORR 100 Church Street
KATHY C. PARK New York, New York 10007
of Counsel 212-356-0855 or -0852
kpark@law.nyc.gov
June 7, 2017
Reproduced on Recycled Paper

TABLE OF CONTENTS
Page
TABLE OF AUTHORITIES .....................................................................iii
PRELIMINARY STATEMENT ................................................................. 1
ISSUES PRESENTED FOR REVIEW ..................................................... 5
STATEMENT OF THE CASE .................................................................. 6
A. Portelos’s history of lashing out in response to perceived

mistreatment by school or union authorities ............................. 6
1. After Principal Hill declined to promote anyone to a

position he wanted, Portelos complained about
Principal Hill ........................................................................... 6
2. After a union leader asked him to curtail his union

activities, Portelos complained about the union leader ......... 9
3. After Principal Hill admonished him for misconduct,

Portelos accused Principal Hill of misconduct ..................... 11
4. After an investigation of his conduct began, Portelos

posted personal grievances against the school and
accused an assistant principal of misconduct ...................... 15
B. Portelos’s temporary removal from his teaching duties,

reassignment to another school, and reinstatement ............... 16
C. This litigation............................................................................ 19
1. The partial grant of summary judgment to defendants....... 20
2. The jury verdict in defendants’ favor ................................... 22
3. The denial of Portelos’s new-trial motion ............................. 25
i
TABLE OF CONTENTS (cont’d)
Page
STANDARD OF REVIEW AND SUMMARY OF ARGUMENT ............ 26
ARGUMENT ........................................................................................... 28
POINT I
THE COURT AND THE JURY PROPERLY REJECTED

PORTELOS’S FIRST AMENDMENT RETALATION
CLAIMS .......................................................................................... 28
A. As a matter of law, when Portelos spoke in his capacity

as a member of the School Leadership Team, he spoke as
a public employee. ..................................................................... 30
B. As the district court properly determined, Portelos’s

pseudonymous speech could not have triggered
retaliation.................................................................................. 35
C. The district court properly denied Portelos’s motion for a

new trial of his First Amendment retaliation claim. ............... 38
POINT II
THE DISTRICT COURT PROPERLY DISMISSED

PORTELOS’S MONELL CLAIMS ................................................. 43
A. On summary judgment, the district court correctly

dismissed Portelos’s Monell claim against the City................. 44
B. At trial, the district court correctly dismissed Portelos’s

Monell claim against the Department. .................................... 45
CONCLUSION ........................................................................................ 48
CERTIFICATE OF COMPLIANCE ........................................................ 49
ii
TABLE OF AUTHORITIES
Page(s)
Cases
Bd. of the Cnty. Comm’rs v. Brown,

520 U.S. 397 (1997) ............................................................................. 44
Burkybile v. Bd. of Educ.,

411 F.3d 306 (2d Cir. 2005) ................................................................ 37
Canton v. Harris,
489 U.S. 378 (1989) ............................................................................. 43
City of Los Angeles v. Heller,

475 U.S. 796 (1986) ............................................................................. 45
Connick v. Myers,
461 U.S. 138 (1983) ....................................................................... 29, 39
Connick v. Thompson,
563 U.S. 51 (2011) ............................................................................... 43
Evans v. Ottimo,
469 F.3d 278 (2d Cir. 2006) ................................................................ 36
Ezekwo v. N.Y.C. Health & Hosps. Corp.,

940 F.2d 775 (2d Cir. 1991) ................................................................ 40
Garcetti v. Ceballos,
547 U.S. 410 (2006) ................................................................. 28, 29, 31
Jones v. Town of East Haven,

691 F.3d 72 (2d Cir. 2012) .................................................................. 43
Lafleur v. Whitman,
300 F.3d 256 (2d Cir. 2002) ................................................................ 36
Lane v. Franks,
134 S. Ct. 2369 (2014) ......................................................................... 29
iii
TABLE OF AUTHORITIES (cont’d)
Page(s)
Lewis v. Cowen,
165 F.3d 154 (2d Cir. 1999) ................................................................ 40
Monell v. Dep’t of Soc. Servs. of the City of New York,

436 U.S. 658 (1978) ..................................................................... passim
New Phone Co., Inc. v. City of New York,

498 F.3d 127 (2d Cir. 2007) .................................................................. 4
Niagara Mohawk Power Corp. v. Jones Chem., Inc.,

315 F.3d 171 (2d Cir. 2003) ................................................................ 26
Ricciuti v. N.Y.C. Transit Auth.,

941 F.2d 119 (2d Cir. 1991) ................................................................ 45
Roe v. City of Waterbury,

542 F.3d 31 (2d Cir. 2008) .................................................................. 43
Ross v. Breslin,
693 F.3d 300 (2d Cir. 2012) ................................................................ 33
Saulpaugh v. Monroe Cmty. Hosp.,

4 F.3d 134 (2d Cir. 1993) .................................................................... 42
Sequa Corp. v. GBJ Corp.,

156 F.3d 136 (2d Cir. 1998) .................................................................. 5
Shrader v. CSX Transportation, Inc.,

70 F.3d 255 (2d Cir. 1995) .................................................................... 4
SongByrd, Inc. v. Estate of Grossman,

206 F.3d 172 (2d Cir. 2000) .................................................................. 4
Sousa v. Roque,
578 F.3d 164 (2d Cir. 2009) .......................................................... 28, 40
iv
Page(s)
Velez v. City of New York,

730 F.3d 128 (2d Cir. 2013) ................................................................ 27
Walton v. Safir,
122 F. Supp. 2d 466 (S.D.N.Y. 2000) .................................................. 38
Weintraub v. Bd. of Educ.,

593 F.3d 196 (2d Cir. 2010) ................................................................ 31
Statutes
42 U.S.C. § 1983 ............................................................................ 1, 19, 43
Educ. Law § 2590-j ............................................................................ 23, 46
Educ. Law § 3020-a ........................................................................... 36, 37
Civil Service Law § 75-b ........................................................ 18, 20, 21, 22
Other Authorities
U.S. Const. amend. I ....................................................................... passim
Fed. R. App. Pro. 3(c)(1)(B) ....................................................................... 4
Fed. R. Civ. Pro. 12(b)(6) ......................................................................... 19
Fed. R. Civ. Pro. 50.................................................................................. 23
Fed. R. Civ. Pro. 51............................................................................ 24, 47
Fed. R. Civ. Pro. 59.......................................................................... passim
Local Civil Rule 6.3, Local Rules of the United States

District Courts for the Southern and Eastern Districts of
New York............................................................................................. 34
v
Page(s)
The Special Commissioner of Investigation, http://nycsci.org

(last visited Jun. 7, 2017) ................................................................... 14
United Federation of Teachers Collective Bargaining

Agreement, Art. 21(G)(8), http://bit.ly/2r5FrUe (last
visited Jun. 7, 2017) ............................................................................ 37
vi
PRELIMINARY STATEMENT
Plaintiff-appellant Francesco Portelos, a tenured science and
technology teacher for the New York City Department of Education,
never hesitated to retaliate when an administrator or union leader took
actions Portelos deemed to be unfair. When, for example, the principal
of his school did not give him (or anyone) the promotion he expected,
Portelos accused the principal of misconduct and later cut off her access
to the school website. And when a union leader asked Portelos to curtail
his union activities, Portelos berated him in front of 60 union members.
The record contains many similar examples of Portelos lashing out at
anyone who dared to deny him what he thought was his due.
Past is prologue. Soon after the Department suspended Portelos
from his teaching duties—based upon insubordination, divisive conduct,
and a threatening email—Portelos commenced this 42 U.S.C. § 1983
action. Ironically enough, Portelos alleged that the City, the
Department, and various administrators retaliated against him in
violation of the First Amendment. The United States District Court for
the Eastern District of New York (Hall, J.) dismissed his claims against
the City on summary judgment and his claims against the Department
at the close of trial. After deliberating, the jury unanimously found that
the individual defendants Principal Linda Hill and Superintendent
Erminia Claudio did not violate Portelos’s First Amendment rights. The
court later denied Portelos’s motion for a new trial, because he had
failed to demonstrate that the jury’s verdict was seriously erroneous or
a miscarriage of justice, or that the court had made substantial errors
in its admission or exclusion of evidence.
This Court should affirm the judgment in favor of defendants.
Portelos primarily argues that the court improperly declined to instruct
the jury that a slew of his complaints constituted protected speech. But
the First Amendment protects a public employee like Portelos only
when he speaks as a citizen on a matter of public concern: it does not
offer shelter when he speaks in his capacity as an employee, or when he
raises issues involving primarily his personal interest. Here, as the
court rightly determined, many of Portelos’s statements fell beyond the
scope of the First Amendment’s protection.
While serving as a member of the School Leadership Team, for
example, Portelos complained that Principal Hill neglected her duty to
consult with team members. His complaints were not protected by the
2
First Amendment because he was speaking as a public employee, not as
a private citizen. When Portelos spoke out at a union meeting and in a
subsequent email to union members, his speech was not protected for a
different reason: the complaints he made were personal in nature and
mainly concerned his own employment situation.
To the extent Portelos premised his First Amendment retaliation
claim on emails he wrote and sent under a pseudonym, his claim failed
for still another reason. His pseudonymous emails could not have
motivated any retaliatory action, because the pseudonym successfully
hid his identity from the defendants.
Finally, the court properly dismissed Portelos’s Monell claims
against the City and the Department. Not only did Portelos fail to
establish that he suffered a First Amendment violation, which alone
was fatal to his Monell claim, but he also failed to demonstrate the
existence of a municipal policy or custom that caused any alleged
violation of his rights.
JURISDICTIONAL STATEMENT
This Court’s jurisdiction “depends on whether the intent to appeal
from [a] decision is clear on the face of, or can be inferred from, the
3
notice[] of appeal.” New Phone Co., Inc. v. City of New York, 498 F.3d
127, 131 (2d Cir. 2007); see also Fed. R. App. Pro. 3(c)(1)(B) (requiring
appellant to “designate the judgment, order, or part thereof being
appealed” in the notice of appeal”). A notice of appeal from a final
judgment brings up for review all reviewable rulings “which produced
the judgment,” SongByrd, Inc. v. Estate of Grossman, 206 F.3d 172, 178
(2d Cir. 2000), but where a party explicitly designates a portion of the
judgment for appellate review, this Court has no jurisdiction to review
the resolution of other antecedent rulings, see Shrader v. CSX
Transportation, Inc., 70 F.3d 255, 256 (2d Cir. 1995).
In his November 2016 notice of appeal, Portelos failed to designate
the district court’s final judgment. Instead, he designated only the jury
verdict and the denial of his post-trial motion (2d Cir. ECF No. 1).1
Thus, this Court lacks jurisdiction to entertain Portelos’s challenges to
the district court’s summary judgment order. As a result, this Court
may not review the district court’s determinations that Portelos’s
speech in connection with the School Leadership Team was not
1The Joint Appendix incorrectly includes an earlier notice of appeal filed on October
1, 2016, which designates only the jury verdict (A. 558).
4
protected; that his pseudonymous complaints could not have been the
basis of any allegedly retaliatory conduct; and that the City was
entitled to dismissal on summary judgment.
To be sure, Portelos attempted to renew his summary judgment
arguments in his post-trial motion. But because “Rule 59 is not a
vehicle for relitigating old issues” or “otherwise taking a second bite at
the apple,” Sequa Corp. v. GBJ Corp., 156 F.3d 136, 144 (2d Cir. 1998)
(internal quotation marks omitted), the district court declined to
address the merits of those arguments. Therefore, Portelos’s
designation of the post-trial order in his notice of appeal does not bring
the summary judgment order up for appellate review.
ISSUES PRESENTED FOR REVIEW
1. Did the district court correctly determine that (a) the
complaints Portelos made as a member of the School Leadership Team
about the principal’s failure to consult with the team, along with his
speech at a union meeting and subsequent email to union members,
which was personal in nature and mainly related to his own situation,
were not protected speech under the First Amendment; and (b) his
5
emails under a pseudonym that hid his identity from defendants could
not have motivated any retaliatory action?
2. Did the district court correctly dismiss Portelos’s Monell claims
against the City and the Department, where (a) he did not suffer an
underlying constitutional violation; (b) he failed to allege or cite
evidence of a municipal policy, practice, or custom that caused a
deprivation of his constitutional rights; and (c) no evidence suggested
that Chancellor Dennis Walcott, the final policymaker, was aware of
any speech that might have motivated retaliation?
STATEMENT OF THE CASE
A. Portelos’s history of lashing out in response to

perceived mistreatment by school or union
authorities
1. After Principal Hill declined to promote

anyone to a position he wanted, Portelos
complained about Principal Hill
Starting in September 2007, Portelos taught science and
technology at I.S. 49 (Joint Appendix (“A.”) 596). One of his primary
accomplishments was creating a website called dreyfus49.com, separate
from the Department’s official website, for the school’s use (A. 601).
6
Portelos paid out of pocket for the domain name registration and
voluntarily worked on the website during his own time (A. 601).
Portelos worked with another technology teacher, Matthew Vallia,
who held the technology coordinator position at the school. Vallia
taught five fewer periods than other teachers because he held a
“compensatory position” (A. 608, 674). As part of his compensatory
position, Vallia was responsible for helping other teachers with
technology issues (A. 674).
In June 2011, at Principal Linda Hill’s request, Portelos agreed to
set up emails on the dreyfus49.com website for the incoming sixth-
graders (A. 675). But then he learned that Vallia was leaving the school,
and that Principal Hill had selected Michael Rossicone, a newer
technology teacher, to take over some of Vallia’s responsibilities (A.
610). Believing that he had been passed over for the lead technology
position, Portelos abruptly refused to set up emails for the incoming
sixth-graders (A. 813, 914-15). He emailed Principal Hill, asserting that
he no longer had time to do “extra” work and expressing his anger that
he was not notified about Vallia’s departure or consulted on how to fill
his position (A. 916-17).
7
Replying to Portelos’s email, Principal Hill explained that she did
not intend to offend him: Vallia had asked her not to say anything
about his departure, and Rossicone was simply taking over some of
Vallia’s teaching duties, without assuming the compensatory time
position (A. 917-18). She advised him that, although she decided to give
Rossicone some of Vallia’s teaching duties, she did not select Rossicone,
or anyone else, for a lead technology position (A. 914).
In an effort to be fair, Principal Hill planned to divide up Vallia’s
compensatory periods among the four or five technology teachers in the
department (A. 694, 813, 815). But Portelos was dissatisfied with
receiving only one compensatory period and refused to accept it (A. 815).
Principal Hill ultimately decided it would be best to dissolve the
compensatory periods altogether (A. 695, 815).
In fall 2011, Portelos was appointed to the vacant position that
Vallia formerly held on the I.S. 49 School Leadership Team, an advisory
body of teachers and parents who help “develop education policies and
ensure implementation of said policies” (A. 283-84). The Chancellor’s
Regulations make clear that parents may not serve as parent members
of the School Leadership Team in schools where they are employed (A.
8
116, 285). The school compensated Portelos approximately $10.00 an
hour for time spent participating in the team, which met once a month
(A. 112, 285). The meeting minutes listed Portelos as representing the
constituency of teachers, thus establishing that he was a teacher
member of the team (A. 125-28).
The School Leadership Team is primarily responsible for
developing the school’s Comprehensive Education Plan (A. 284). In
December 2011, Portelos emailed certain members of the team,
claiming that Principal Hill had submitted the Comprehensive
Education Plan without the team’s input in violation of the Chancellor’s
Regulations and New York State law (A. 292). Principal Hill explained
that the version she had submitted was only a draft (A. 291-93).
2. After a union leader asked him to curtail his

union activities, Portelos complained about the
union leader
In January 2012, Portelos began posting several messages about
I.S. 49 students and teachers on social media. On January 20, for
example, Portelos posted on Facebook that a student who tried to scare
him as a joke was “so lucky that I didn’t instinctively tiger punch him in
the throat” (A. 704). A few days later, the New York Post contacted
9
Portelos about a separate Facebook post that he wrote, where he noted
that a teacher’s iPhone was stolen, that the police could not locate it,
and that he was able to retrieve it using an iPhone finder (A. 629).
Principal Hill met with Portelosto discuss other Facebook posts
that upset his colleagues (A. 630, 634). Apparently, Portelos’s colleagues
were particularly upset over one of his posts that appeared to call them
losers (A. 630).
On January 26, union leader Richard Candia advised Portelos
that he wanted him off the union consultation committee (A. 634-35).2
He also asked Portelos to resign as a union delegate (A. 634). The next
day, Portelos attended a union meeting, where 60 members were in
attendance (A. 635). He started off by remarking, “et tu, Brutus?” (A.
635). He lamented that staff members were stabbing each other in the
back and giving the administration “meaningless Facebook posts to
cause issues” (A. 635). He also complained that Principal Hill had
admonished him about it (A. 635).
2The union consultation committee is a group of union members selected by the

union leader to discuss school issues that should be brought before the principal (A.
634-35).
10
The next day, Candia emailed Portelos, asking him again to resign
from his union delegate position (A. 635-36). Copying the list-serve of
union members, Portelos replied with his refusal to resign (A. 635-36,
931). He insisted, “I made a commitment to our staff and I will keep it
throughout the term” (A. 931). He further complained: “Ever since I
acquired the position of delegate [Candia] stopped me from
communicating with the staff, met with the administration countless
times without me and rejected my requests to share important
information I found at delegate meetings” (A. 931). As for his removal
from the union consultation committee, Portelos acknowledged that
Candia held the authority to require that, so he simply remarked, “[t]oo
bad I had some ideas” (A. 931). Portelos ended with his email with his
“hope for the sake of the community this can be worked out” (A. 931).
3. After Principal Hill admonished him for

misconduct, Portelos accused Principal Hill of
misconduct
Following Portelos’s email to the list-serve of union members,
Principal Hill suspended Portelos’s dreyfus49.com email account
because she did not want staff members involved in a “back-and-forth
war of words on the internet” (A. 820). When Portelos discovered that
11
he could not access his dreyfus49.com account, he used a secondary
account to disable Principal Hill’s access to the website, without
notifying her of his actions (A. 636, 706).
In February 2012, the school held three disciplinary conferences
with Portelos (A. 649, 836, 937-39). The first conference concerned his
mass email to staff without Principal Hill’s permission, when Principal
Hill had previously instructed him not to send mass emails without her
approval (A. 649, 820, 939). The second conference addressed Portelos’s
recent confrontation with Candia and another teacher, Susanne
Abramowitz, after Portelos learned that she was one of the staff
members upset over his recent Facebook posts (A. 649, 938). According
to witness statements from Candia and Abramowitz, Portelos cursed at
them, acted erratically, and knocked papers out of Abramowitz’s hands
(A. 649, 932-33). The third conference concerned Portelos staying at the
school past working hours without first notifying Principal Hill (A. 836-
37, 937). Principal Hill deemed Portelos’s conduct insubordinate
because she had explicitly explained to staff that, due to recent security
protocols, she needed to approve requests in advance if staff wished to
stay in the school past 5:30 p.m. (A. 655, 937).
12
On February 14, Portelos met with Superintendent Erminia
Claudio, Principal Hill, and a union representative (A. 651, 747).
During the meeting, Portelos complained that he did not understand
why he was the target of what he called workplace bullying (A. 651).
Portelos admitted that he had disabled Principal Hill’s access to the
website because he was angry that he had not been selected to take
Vallia’s position (A. 747). Portelos also testified at trial that Principal
Hill stated during the meeting that Portelos had been looking into her
time cards (A. 651).
It was agreed at the meeting that Portelos would transfer
ownership of the dreyfus49.com website to Principal Hill (A. 655, 707,
747, 838). After speaking with his attorney, however, Portelos decided
not to transfer ownership after all (A. 748). Portelos emailed Principal
Hill, claiming that the website belonged to him and that he had every
right to it (A. 748, 838). In March 2012, after Portelos refused to
transfer ownership of the website, Principal Hill directed him to shut it
down entirely (A. 708, 838).
Also in March 2012, Portelos submitted a FOIA request in his own
name for Principal Hill’s time cards (A. 663). He had previously sent
13
emails about Principal Hill to the Special Commissioner of
Investigation for the New York City School District (SCI), an external
agency that operates under the umbrella of the New York City
Department of Investigation (A. 303). See The Special Commissioner of
Investigation, http://nycsci.org (last visited Jun. 7, 2017). Those emails
alleged that Hill was engaged in financial misconduct, but Portelos had
sent them under the pseudonym “Liz Simpson” (A. 303). There is no
evidence that school administrators were aware that Portelos was “Liz
Simpson.”
Following his FOIA request, Portelos filed a report with the
Department’s Office of Special Investigations (OSI), alleging that
Principal Hill was double dipping by billing simultaneously for two
overtime programs that were scheduled at the same time (A. 663, 844).
At trial, Principal Hill explained that the simultaneous billing was
inadvertent and that she had repaid the $801 she owed (A. 842-44).
14
4. After an investigation of his conduct began,

Portelos posted personal grievances against
the school and accused an assistant principal
of misconduct
Beginning in January 2012, Portelos faced multiple SCI
investigations arising from allegations that he had conducted real
estate business in the classroom and had separately sent a text message
to a student in the guise of Principal Hill (A. 658-60). 3 In March 2012,
shortly after the investigations commenced, Portelos launched a blog
called protectportelos.org (A. 660-61). On his blog, he posted emails,
letters of recommendation, satisfactory observations, and disciplinary
letters, in addition to posts detailing his complaints of retaliatory
conduct (A. 660). The New York Post contacted him for a comment and
published an article about the blog on March 18, 2012 (A. 661).
The following month, Portelos used his phone to record a video of
Assistant Principal Denise Diacomanolis interacting with a student in a
school hallway (A. 713). Portelos claimed to have shot the video because
he believed something inappropriate was happening (A. 713). Later,
3 The real estate allegations were later withdrawn (A. 848). Portelos claimed that
the text-message allegation was “unsubstantiated” (A. 659-60).
15
Portelos submitted a complaint to SCI concerning the video (A. 714).
While the investigation was open and ongoing, Portelos posted the video
on YouTube without permission from the child’s parents (A. 735).
Superintendent Claudio reported the uploading of the video to SCI,
concerned that Portelos had uploaded the child’s image on a public
forum (A. 780).
Then, on April 18, Portelos lodged an allegation against Assistant
Principal Diacomanolis with SCI and OSI (A. 665). He alleged that
Assistant Principal Diacomanolis had improperly pulled an eighth-
grader out of class and put him in a sixth-grade class for three weeks
because he was misbehaving (A. 665).
B. Portelos’s temporary removal from his teaching

duties, reassignment to another school, and
reinstatement
School administrators grew increasingly concerned about Portelos:
among other things, he had repeatedly defied Principal Hill’s directives
and his activities were dividing the school (A. 748, 839). Principal Hill
was particularly alarmed when, in April 2012, Portelos sent what she
perceived to be a threatening email to teaching staff, paraprofessionals,
and librarians (A. 841). In his email, Portelos warned that “anyone who
16
has made false statements” should “find a way to rectify or retrace them
very quickly,” and he might then “show mercy” (A. 719, 947).
For these reasons, Superintendent Claudio recommended
Portelos’s removal from I.S. 49 (A. 748). On April 25, Portelos was
suspended from his teaching duties and reassigned to Petrides Center
in Staten Island, a central administrative office (A. 661, 749).
Superintendent Claudio, however, soon recommended another transfer
(A. 750). Portelos had been found lurking away from his assigned area,
and Superintendent Claudio was concerned that he would be able to
access confidential information stored at Petrides—which included staff
and student records, budget materials, and ungraded tests—and upload
it onto his website (A. 749-50). Portelos was soon reassigned to a school
in Queens (A. 779). In September 2013, after Portelos asked to move
closer to his home in Staten Island, he was reassigned to a school in
Brooklyn (A. 663-64).
During his reassignment, Portelos blogged about his experience
and shared his comments on Facebook and Twitter, which generated
media coverage (A. 662-63). He also purchased the domain name
welearnandgrowtogether.com, which was an expired website initially
17
linked to the official Department webpage that I.S. 49 had formerly
used as its school website (A. 719-20). Even though Principal Hill
included the site in her signature block, Portelos changed the settings to
reroute visitors to another website, occupywarrenstreet.com, where he
posted a photo of I.S. 49 partly submerged like a sinking ship (A. 719-
220, 722, 841). Portelos also created a mock local newspaper article,
falsely claiming that I.S. 49 was going to be closed down (A. 841).
On December 4, 2012, Portelos attended a Community Education
Council (CEC) meeting (A. 665). The CEC, whose members are parents
elected by parent-teacher associations, makes recommendations to the
superintendent and chancellor (A. 665). It convenes a public meeting
once a month (A. 665-66). Superintendent Claudio, Principal Hill, and
seven or eight parents attended the meeting (A. 665-66). There, Portelos
complained about being targeted as a villain at the school (A. 666). At
one point, Portelos blurted out that an assistant principal was
inappropriately touching children and that there was financial
misconduct in the school (A. 666).
In 2013, the school preferred formal disciplinary charges against
Portelos (A. 664). Having obtained tenure in 2010, Portelos was
18
entitled to an arbitral hearing under Educ. Law § 3020-a (A. 647). The
arbitrator sustained 11 out of 38 specifications and ordered that
Portelos be returned to the classroom (A. 664). According to Portelos,
the sustained charges primarily concerned contacting neighborhood
parents about what was going on in the school and “changing”
Principal Hill’s administrative access to the dreyfus49.com website (A.
664). After the arbitrator issued the decision in May 2014, the
Department concluded Portelos’s administrative reassignment (A. 664).
C. This litigation
Portelos commenced this § 1983 action in June 2012, asserting
that the City, the Department, Principal Hill, and Superintendent
Claudio retaliated against him for engaging in protected speech under
the First Amendment (A. 45-57). He additionally asserted that
defendants committed violations under New York Civil Service Law
§ 75-b (A. 57-58).
In March 2013, the district court denied defendants’ motion to
dismiss pursuant to Rule 12(b)(6) (A. 6; E.D.N.Y. ECF No. 25). The
court determined that the complaint’s allegations supported the
reasonable inference that Portelos’s speech fell within the protection of
19
the First Amendment (id., at 2-4). The court also declined to dismiss
Portelos’s claims under § 75-b, holding that the allegations sufficed to
survive a motion to dismiss (id., at 4-6).
1. The partial grant of summary judgment to

defendants
Later, the district court partially granted defendants’ motion for
summary judgment (Special Appendix “SA” 18). First, the court
dismissed Portelos’s First Amendment retaliation claim insofar as it
was based on (1) his speech in connection with the School Leadership
Team; and (2) the allegedly retaliatory conduct that occurred before
mid-April 2012, based on his pseudonymous complaints to the SCI (SA
18). When Portelos spoke as a member of the School Leadership Team,
the court held, he was carrying out his official duties, and thus his
speech fell outside the protection of the First Amendment (SA 7-11). As
for Portelos’s communications as “Liz Simpson,” the court continued, he
failed to create a genuine issue of fact as to whether any of the
defendants were aware that he was “Liz Simpson” (SA 11). The court,
however, declined to dismiss Portelos’s First Amendment retaliation
20
claim to the extent that it was predicated on other instances of allegedly
protected speech.
Second, the court dismissed the City of New York and Chancellor
Dennis Walcott as defendants (SA 13). With respect to the City, the
court determined that Portelos failed to allege or cite evidence of any
municipal policy, practice, or custom of the SCI or OSI that caused a
deprivation of Portelos’s constitutional rights (SA 16). The court held
that Chancellor Walcott was entitled to qualified immunity as a matter
of law (SA 13-14). Although Chancellor Walcott was involved in
authorizing Portelos’s reassignment, the court reasoned, no reasonable
juror could find that he violated any clearly established law, given the
number and severity of the complaints lodged against Portelos that
were unrelated to his allegedly protected speech (SA 14-15). Portelos’s
Monell claim against the Department survived summary judgment,
however, because even a single act of a municipal policymaker with
final decision-making authority would be sufficient to support a Monell
claim (SA. 14-15).
Third, the court dismissed Portelos’s claims under New York Civil
Service § 75-b (SA 16). His § 75-b claims against Principal Hill and
21
Superintendent Claudio failed because § 75-b does not permit claims
against individual employees (SA 16-17). The court dismissed Portelos’s
§ 75-b claims against the remaining defendants because he had failed to
exhaust his administrative remedies (SA 17-18).
2. The jury verdict in defendants’ favor
Before trial, the district court granted defendants’ motion in
limine to preclude Portelos from presenting evidence regarding the
allegations—of Principal Hill’s supposed financial misconduct—made
under the “Liz Simpson” pseudonym (A. 569-70). But the court
permitted Portelos to present evidence demonstrating that Principal
Hill, independent of the “Liz Simpson” complaints, later became aware
that Portelos was investigating this issue (A. 570).
During trial, the jury heard testimony from three witnesses
regarding the administrators’ alleged retaliatory conduct. Principal Hill
and Superintendent Claudio testified in detail about the problems
Portelos caused in the school, especially after he believed he had been
passed over for a promotion. Portelos, in turn, provided his own
account, stressing his prior satisfactory record and insisting that the
school administrators unfairly targeted him for retaliation.
22
At the close of evidence, the court granted defendants’ Rule 50
motion to dismiss the Department as a defendant (A. 865). First, the
court determined that Portelos had failed to demonstrate that
Superintendent Claudio had final decision-making authority to suspend
or bring disciplinary charges against him, or that her recommendation
to remove him was a final decision (A. 862-65). Second, although
Chancellor Walcott was a policymaker with final decision-making
authority, the evidence did not show that he or his designees were
aware that Portelos had lodged allegations of timesheet fraud against
Principal Hill (A. 863-65). The court thus concluded that the
Department was not liable on a Monell theory of liability (A. 865-66).
After closing arguments, Portelos moved for reconsideration of the
court’s decision to dismiss the Department as a defendant, belatedly
citing Educ. Law § 2590-j as authority establishing that Superintendent
Claudio was indeed a policymaker with final decision-making authority,
and citing evidence purportedly showing that she had exercised this
authority (A. 951-53). Despite Portelos’s failure to comply with the
court’s individual practices in his motion, the court denied his motion
because the evidence he cited was outside the trial record, and, in any
23
event, Fed. R. Civ. Pro. 51 barred him from making belated objections
to the jury instructions after summations (A. 952-53).
In finalizing the jury charge, the court treated only some of
Portelos’s speech as protected under the First Amendment (A. 798-800,
850-51). Although Portelos claimed over 20 instances of protected
speech, the court determined that many of the relevant remarks were
not protected speech because they concerned Portelos’s personal
interest (A. 798-800, 850-51). The court also noted that Portelos’s
launch of a website, recording of a video, and certain other activities did
not constitute First Amendment speech (A. 799).
Accordingly, the district court instructed the jury that Portelos’s
retaliation claim could be based on only the following instances of
protected speech: (1) his complaint to OSI alleging that Principal Hill
misappropriated funds as a result of her timecard entries; (2) his April
18, 2012 complaint to the OSI and SCI alleging that Assistant Principal
Diacomanolis placed an eighth-grader in a sixth-grade class; (3) his
June 2012 complaint to SCI alleging that Assistant Principal
Diacomanolis engaged in corporal punishment; and (4) his December 4,
2012 statements at a Community Education Council meeting
24
complaining of financial misconduct and accusing the assistant
principal of inappropriately touching children (A. 528).
The jury returned a verdict in defendants’ favor (A. 530). The jury
found that Portelos failed to prove by a preponderance of the evidence
that his protected speech was a substantial or motivating factor in a
defendant’s decision to take adverse employment action against him (A.
530).
3. The denial of Portelos’s new-trial motion
Following the jury verdict, Portelos moved for a new trial under
Rule 59 (A. 534-56). After hearing oral argument, the court denied the
motion, citing Portelos’s failure to put forth evidence or argument that
the jury’s verdict was seriously erroneous or a miscarriage of justice, or
that the court made substantial errors in admitting or excluding
evidence (A. 26). The court further noted that, to the extent Portelos’s
Rule 59 motion was seeking reconsideration of the summary judgment
decision, his time to file a motion for reconsideration of that decision
had long expired, since it needed to have been filed 14 days after the
court’s entry of the order (A. 26).
25
STANDARD OF REVIEW AND

SUMMARY OF ARGUMENT
This Court reviews the district court’s grant of summary judgment
de novo, construing all inferences in the non-moving party’s favor.
Niagara Mohawk Power Corp. v. Jones Chem., Inc., 315 F.3d 171, 175
(2d Cir. 2003). Applying this standard, this Court should—assuming
jurisdiction (see pages 3-5 above)—affirm the district court’s partial
grant of summary judgment to defendants. The district court correctly
dismissed Portelos’s First Amendment retaliation claim to the extent
that it was based on his allegations that Principal Hill submitted the
Comprehensive Education Plan without input from the School
Leadership Team, because he did not make those statements as a
private citizen. The court also properly dismissed Portelos’s First
Amendment claim to the extent he alleged retaliation based upon his
January 2012 emails to SCI made under the pseudonym “Liz Simpson,”
because he failed to cite record evidence creating a genuine issue of fact
as to whether any of the defendants were aware that he had sent those
pseudonymous emails. And the court rightly dismissed the City as a
defendant, because the court determined that Portelos failed to allege or
26
cite evidence of any municipal policy, practice, or custom of the SCI or
OSI that caused a deprivation of his constitutional rights
Because Portelos argues that the district court improperly
instructed the jury, this Court reviews de novo the district court’s denial
of Portelos’s Rule 59 motion for a new trial. Velez v. City of New York,
730 F.3d 128, 134 (2d Cir. 2013). Here, the court correctly instructed
the jury on which of Portelos’s statements constituted protected speech,
after determining that many of the alleged utterances involved matters
of personal interest or were not speech at all within the meaning of the
First Amendment. The court also correctly determined that Portelos
was not entitled to a new trial based on the pre-trial dismissal of the
Department as a defendant: even if Superintendent Claudio had
exercised final decision-making authority here, as Portelos claimed, the
jury found that she did not retaliate against Portelos in violation of the
First Amendment, so no claim could lie against the Department based
on her conduct.
27
ARGUMENT
POINT I
THE COURT AND THE JURY PROPERLY

REJECTED PORTELOS’S FIRST
AMENDMENT RETALATION CLAIMS
The First Amendment protects a public employee’s speech only
when “the employee [speaks] as a citizen on a matter of public concern.”
Garcetti v. Ceballos, 547 U.S. 410, 418 (2006). If both prongs of this test
are satisfied—i.e., the employee spoke as a citizen rather than as an
employee, and spoke on a matter of public concern—courts then apply a
balancing test to determine “whether the relevant government entity
had an adequate justification for treating the employee differently from
any other member of the general public.” Id. (citation omitted). But if
the court determines that the employee “either did not speak as a
citizen or did not speak on a matter of public concern,” the inquiry ends
there: “‘the employee has no First Amendment cause of action based on
his or her employer’s reaction to the speech.’” Sousa v. Roque, 578 F.3d
164, 170 (2d Cir. 2009) (quoting Garcetti, 547 U.S. at 418).
This two-prong test recognizes that “[s]peech by citizens on
matters of public concern lies at the heart of the First Amendment,
which ‘was fashioned to assure unfettered interchange of ideas for the

28
bringing about of political and social changes desired by the people.’”
Lane v. Franks, 134 S. Ct. 2369, 2377 (2014) (quoting Roth v. United
States, 354 U.S. 476, 484 (1957)). At the same time, the test also
accounts for the government’s countervailing interest in controlling the
operation of its workplaces. See Connick v. Myers, 461 U.S. 138, 143
(1983) (noting the “common-sense realization that government offices
could not function if every employment decision became a constitutional
matter”). As a practical reality, “[g]overnment employers, like private
employers, need a significant degree of control over their employees’
words and actions; without it, there would be little chance for the
efficient provision of public services.” Garcetti, 547 U.S. at 418.
Restricting speech that owes its existence to a public employee’s
professional responsibilities also does not infringe upon any liberties
the employee might have enjoyed as a private citizen: “[i]t simply
reflects the exercise of employer control over [speech] the employer
itself has commissioned or created.” Garcetti, 547 U.S. at 438.
Here, the district court properly determined that many of
Portelos’s statements fell beyond the scope of the First Amendment’s
protection. Portelos’s complaints as a member of the School Leadership
29
were not protected, because he was speaking as a public employee when
he made those statements. To the extent Portelos premised his First
Amendment retaliation claim on emails he wrote under a pseudonym,
his pseudonymous emails could not have motivated any retaliatory
action because he had remained anonymous. Finally, Portelos’s speech
at a union meeting and in a subsequent email to union members was
not entitled to First Amendment protection because the complaints he
made primarily concerned his own employment situation.
A. As a matter of law, when Portelos spoke in his

capacity as a member of the School Leadership
Team, he spoke as a public employee.
At the summary judgment stage, the district court correctly
dismissed Portelos’s First Amendment claim to the extent it was based
on his allegations that Principal Hill submitted the Comprehensive
Education Plan without input from the School Leadership Team,
because he did not make those statements as a private citizen. Those
statements were made pursuant to his official duties, and thus
unprotected by the First Amendment.
Speech made pursuant to a public employee’s official duties is
defined as “speech that owes its existence to a public employee’s
30
professional responsibilities.” Weintraub v. Bd. of Educ., 593 F.3d 196,
201 (2d Cir. 2010) (quoting Garcetti, 547 U.S. at 421). Whether a public
employee spoke “pursuant to” his or her official duties is an objective,
practical inquiry. Id. at 202.
This Court has explained that, even if a public employee’s speech
“is not required by, or included in, [his] job description, or [made] in
response to a request by the employer,” he speaks as an employee and
not as a citizen if the speech is “‘part-and-parcel of his concerns’ about
his ability to ‘properly execute his duties.’” Weintraub, 593 F.3d at 203
(quoting Williams v. Dallas Indep. Sch. Dist., 480 F.3d 689, 694 (5th
Cir. 2007)). In Weintraub, for example, this Court held that the filing of
a union grievance by a teacher regarding school administrators’
handling of discipline problems in his classroom was not protected,
because it implicated the teacher’s “core duties” of “maintaining class
discipline.” Id. at 198.
So too here. The summary judgment record establishes that
Portelos’s speech in connection with his participation on the School
Leadership team directly involved his concerns about his ability to
perform his duties. Indeed, the School Leadership Team is primarily
31
responsible for developing the school’s Comprehensive Education Plan
(A. 284). Thus, when Portelos complained about Principal Hill’s
submission of the Comprehensive Education Plan without input from
the School Leadership Team, it squarely implicated his core duties as a
member of that team.
The summary judgment record also firmly demonstrates that
Portelos was acting as a teacher member, not a parent citizen, in his
communications about the School Leadership Team. Not only did the
school compensate Portelos for his service on the team, the meeting
minutes also listed Portelos as representing the constituency of teachers
(A. 112, 125-28, 285). Although Portelos insists that he held the status
of a parent because his children would one day attend I.S. 49, the
Chancellor’s Regulations make clear that parents may not serve as
parent members of the School Leadership Team in schools where they
work (A. 116, 285). Further, Portelos’s children were not even attending
I.S. 49 at the time.
Contrary to Portelos’s assertion, it is of no moment that he was
appointed to his position on the School Leadership Team, rather than
elected to it by other teachers (App. Br. at 28). That the school
32
appointed Portelos to the position only supports the notion that his
service on the School Leadership Team was part of his official duties as
a public employee.
And even if, as Portelos asserts in his brief, the school also
compensated parent members for their service on the School Leadership
Team (a fact that is nowhere to be found in the summary judgment
record), it would not change the outcome here. Compensation was just
one factor among the many considerations showing that Portelos spoke
in his capacity as a public employee.
Portelos also misguidedly insists that his allegations about
Principal Hill’s submission of the Comprehensive Education Plan raised
matters of public concern (App. Br. at 30). Because Portelos was
speaking as a public employee, it does not matter whether he spoke on
an issue of public concern: as a threshold requirement, he had to have
made those statements as a private citizen. See Ross v. Breslin, 693
F.3d 300, 306 (2d Cir. 2012) (finding that, even though plaintiff’s speech
concerning improper payments to school employees was on a matter of
public concern, it was not protected by the First Amendment because it
was made pursuant to her duties as a payroll clerk typist).
33
Equally meritless is Portelos’s assertion that he was unfairly
prejudiced by the court’s “very late” ruling on summary judgment that
his statements regarding the submission of the Comprehensive
Education Plan were unprotected (App. Br. at 28-30). Contrary to
Portelos’s argument, the district court’s earlier ruling on the motion to
dismiss—namely, that the complaint supported the “reasonable
inference” that Portelos was speaking as a private citizen on this
issue—did not “contradict” its later summary judgment ruling (App. Br.
at 28-29). The court’s ruling on the dismissal motion did not provide a
reasonable basis for Portelos to believe that the claim would also
survive summary judgment. Following discovery, the court properly
held that Portelos had failed to adduce evidence creating a genuine
issue of fact that he was speaking as a private citizen. After the court
rendered its summary judgment decision and order, Portelos could have
sought reconsideration of that ruling within 14 days of the court’s entry
of the order, if he truly believed that it would severely prejudice his
presentation of the case at trial. See Local Civil Rule 6.3, Local Rules of
the United States District Courts for the Southern and Eastern
Districts of New York. He did not.
34
Thus, the district court correctly ruled that when Portelos
complained about Principal Hill in his capacity as a member of the
School Leadership Team, he spoke as a public employee, without First
Amendment protections.
B. As the district court properly determined,

Portelos’s pseudonymous speech could not have
triggered retaliation.
At the summary judgment stage, the district court also correctly
dismissed Portelos’s First Amendment claim to the extent it was based
on the January 2012 emails he sent to SCI under the pseudonym “Liz
Simpson” (SA 11). The court determined that Portelos had failed to cite
record evidence creating a genuine issue of fact as to whether any of the
defendants were aware that he was “Liz Simpson” (SA 11). As long as
Portelos hid successfully behind his pseudonym, the court soundly
reasoned, it would have been impossible for the defendants to retaliate
again him based upon the content of his pseudonymous speech (SA 11).
Based on its summary judgment ruling, the district court correctly
granted defendants’ motion in limine to preclude Portelos from
presenting evidence regarding the allegations—of Principal Hill’s
supposed financial misconduct—made under this pseudonym (A. 569).
35
At the same time, the court permitted Portelos to present evidence
demonstrating that Principal Hill, independent of the “Liz Simpson”
complaints, later became aware that Portelos was investigating this
issue (A. 570, 644).
Indeed, as the district court noted in its summary judgment
ruling, the arbitrator had already found, after the Educ. Law § 3020-a
hearing, a lack of credible evidence that Principal Hill knew, before
mid-April 2012, that Portelos had reported these allegations
anonymously on January 26, 2012 (SA 11; E.D.N.Y. ECF No. 105, Ex.
R, at 43 n.17). The arbitrator’s finding, the court properly recognized,
was entitled to preclusive effect (SA 11; A. 569-71).
Under New York law, the doctrine of collateral estoppel bars re-
litigation of an issue when: “(1) the identical issue necessarily was
decided in the prior action and is decisive of the present action; and
(2) the party to be precluded from relitigating the issue had a full and
fair opportunity to litigate the issue in the prior action.” Evans v.
Ottimo, 469 F.3d 278, 281 (2d Cir. 2006). The bar can apply even if the
tribunals or causes of action differ. Lafleur v. Whitman, 300 F.3d 256,
271 (2d Cir. 2002). This Court has established that § 3020-a findings
36
are entitled to preclusive effect. Burkybile v. Bd. of Educ., 411 F.3d 306,
308 (2d Cir. 2005). Thus, following the arbitrator’s ruling, the district
court properly barred Portelos from relitigating the “Liz Simpson” issue
in his federal lawsuit.
Portelos protests that he was unable to present evidence that
Principal Hill had received a series of text messages between Portelos
and Candia that suggested her awareness, as of January 2012, that
Portelos had initiated an SCI investigation against her regarding the
time cards (App. Br. at 25). But the district court correctly determined
that Portelos was collaterally estopped from relitigating this fact.
Indeed, Portelos does not claim that he lacked a full and fair
opportunity to engage in the extensive discovery procedures available to
him at the § 3020-a hearing. 4
Next, Portelos mistakenly contends that when the jury
interrupted its deliberations to request and review his direct testimony
regarding when he reported Principal Hill’s misappropriation of funds
(A. 960), the court improperly prevented the jury from considering his
4See United Federation of Teachers Collective Bargaining Agreement, Art. 21(G)(8),

at 159-61, http://bit.ly/2r5FrUe (last visited Jun. 7, 2017).
37
testimony that Principal Hill mentioned Portelos’s time card inquiries
on February 14, 2012 (App. Br. at 27). That portion of Portelos’s
testimony did not answer the jury’s inquiry, however, because it did not
concern when he reported his suspicions (A. 960).
Portelos further cites Walton v. Safir, 122 F. Supp. 2d 466
(S.D.N.Y. 2000), in an effort to support the proposition that anonymous
speech could be considered protected speech (App. Br. at 27). But in
addition to being non-binding, that case is entirely inapposite. In
Walton, the court found that the defendants were aware of the speaker’s
identity, despite her attempts to disguise herself. Id. at 478-79. By
contrast here, no evidence created a genuine issue of fact regarding
defendants’ ability to connect “Liz Simpson” to Portelos. Thus, the
district court correctly ruled that as long as Portelos’s emails remained
anonymous, they could not have motivated retaliation.
C. The district court properly denied Portelos’s

motion for a new trial of his First Amendment
retaliation claim.
Based upon his assertion that the court had improperly instructed
the jury regarding protected speech, Portelos moved under Rule 59 for a
new trial of his First Amendment claim. Because the court’s instruction
38
was proper, this Court should affirm the district court’s denial of
Portelos’s Rule 59 motion.
The district court correctly instructed the jury that Portelos
engaged in protected speech only when he complained to OSI that
Principal Hill used her time card entries to misappropriate funds;
complained to the OSI and SCI that Assistant Principal Diacomanolis
placed an eighth-grader in a sixth-grade class and separately engaged
in corporal punishment; and, during a Community Education Council
meeting, complained of financial misconduct and accused the assistant
principal of inappropriately touching children (A. 528). The court
properly determined as a matter of law that Portelos did not engage in
any other protected speech.
Much of Portelos’s speech was unprotected because it did not
address matters of public concern. The U.S. Supreme Court has defined
“a matter of public concern” as one that “relat[es] to any matter of
political, social, or other concern to the community.” Connick v. Myers,
461 U.S. 138, 146 (1983). “Whether an employee’s speech addresses a
matter of public concern is a question of law for the court to decide,
taking into account the content, form, and context of a given statement
39
as revealed by the whole record.” Lewis v. Cowen, 165 F.3d 154, 163 (2d
Cir. 1999). In making this determination, the speaker’s motive is
relevant, see Lewis, 165 F.3d at 163-64, although “not dispositive,” see
Sousa v. Roque, 578 F.3d 164, 174 (2d Cir. 2009).
Here, Portelos insists that he engaged in over 20 instances of
protected speech (App. Br. at 31). But the court correctly ruled that the
bulk of these utterances were not protected because they were primarily
motivated by and dealt with Portelos’s individual employment
situation. “[S]peech on a purely private matter, such as an employee’s
dissatisfaction with the conditions of his employment, does not pertain
to a matter of public concern.” Lewis, 165 F.3d at 164; see also Ezekwo v.
N.Y.C. Health & Hosps. Corp., 940 F.2d 775, 781 (2d Cir. 1991) (holding
that medical resident’s complaints about aspects of residency program
that negatively affected her did not implicate matters of public concern).
Portelos argues, in particular, that his speech at the union
meeting and subsequent email to union members raised matters of
public concern, because he sought to address “strife between
administration and staff” in a public school (App. Br. 19-23). But the
record shows that his complaints were largely limited to his own
40
circumstances. At the meeting, he remarked, “et tu, Brutus?” (A. 635)—
a comment conveying his belief he had been betrayed. He further
lamented that staff members were stabbing each other in the back and
giving the administration meaningless Facebook posts (that he
authored) to “cause issues” and, significantly, complained that Principal
Hill had admonished him (A. 635).
Similarly, Portelos’s subsequent email responding to Candia’s
request for him to resign as a union delegate also mainly concerned his
own situation. Indeed, Portelos emphasized his personal “commitment
to our staff” and his intention to keep his commitment “throughout the
term” (A. 931). He further complained that, “[e]ver since [he] acquired
the position of delegate [Candia] stopped him from communicating with
the staff, met with the administration countless times without [him]
and rejected [his] requests to share important information [he] found at
delegate meetings” (A. 931). Portelos’s peripheral remarks that he had
“some ideas” and “hope[d] for the sake of the community this can be
worked out” falls short of raising a matter of public concern (A. 931),
given the overall context of the communication. Thus, Portelos’s
complaints about Candia were not protected under the First
41
Amendment, because they were “personal in nature and generally
related to [his] own situation.” Saulpaugh v. Monroe Cmty. Hosp., 4
F.3d 134, 143 (2d Cir. 1993).
Portelos does not attempt to explain why the court erred in
rejecting other instances of speech as protected by the First
Amendment, other than to suggest that the court did not give him
enough time to present his case (App. Br. at 30-31). And he distorts the
record in this regard, because the court simply urged Portelos to
proceed expeditiously, in a streamlined fashion (A. 467, 645). In fact,
the court made clear that it was not trying to “preclude [Portelos] from
presenting [his] case,” but urged him to “present it in as effective a
manner as possible, in light of the jurors’ time” (A. 645). In any event,
because Portelos never objected at trial to the amount of time he had to
present his case, he failed to preserve the issue for his Rule 59 motion,
or for this appeal.
Thus, the district court correctly denied Portelos’s motion for a
new trial with respect to his First Amendment retaliation claim.
42
POINT II
THE DISTRICT COURT PROPERLY

DISMISSED PORTELOS’S MONELL
CLAIMS
Under 42 U.S.C. § 1983, the City may not be held liable for the
unconstitutional conduct of its employees solely on the theory of
respondeat superior. Monell v. Dep’t of Soc. Servs. of the City of New
York, 436 U.S. 658, 691, 694 (1978); Roe v. City of Waterbury, 542 F.3d
31, 36 (2d Cir. 2008). Rather, a plaintiff must establish the existence of
an official policy or custom that caused the claimed deprivation of a
constitutional right. See Monell, 436 U.S. at 694; Canton v. Harris, 489
U.S. 378, 385 (1989). An official municipal policy or custom may be
(1) an act of a policymaking official; (2) a formal policy officially
promulgated or endorsed by the municipality; (3) a practice so
persistent and widespread as to practically have the force of law; or
(4) a practice inferred from the deliberate indifference of supervisory
officials. See, e.g., Connick v. Thompson, 563 U.S. 51, 61 (2011); Jones v.
Town of East Haven, 691 F.3d 72, 80-81 (2d Cir. 2012).
Here, the district court properly dismissed Portelos’s Monell
claims against the City and the Department. No evidence supports his
43
theory that a municipal policy or custom was the driving force behind a
constitutional deprivation that he suffered.
A. On summary judgment, the district court correctly

dismissed Portelos’s Monell claim against the City.
With respect to the City, the court correctly determined that
Portelos failed to allege or cite evidence of any municipal policy,
practice, or custom of the SCI or OSI that caused a deprivation of
Portelos’s constitutional rights (SA 16). Thus, the court properly
dismissed the City as a defendant at the summary judgment stage.
Portelos insists that he adequately demonstrated that the City
had engaged in an unofficial policy of whitewashing or delaying his
allegations reported to SCI (App. Br. 34-35). But even if this were true,
Portelos cited no evidence connecting the SCI’s practices to the school
administrators’ allegedly retaliatory practices, so as to establish that
the supposed policy “caused” him to suffer a constitutional violation.
Indeed, “[w]here a plaintiff claims that the municipality has not directly
inflicted an injury, but nonetheless has caused an employee to do so,
rigorous standards of culpability and causation must be applied” to
protect against respondeat superior liability. Bd. of the Cnty. Comm’rs v.
44
Brown, 520 U.S. 397, 405 (1997) (citations omitted). Here, Portelos
failed to cite evidence establishing the critical element of causation.
Moreover, Portelos cites only his own personal experience, falling
short of demonstrating the existence of a pervasive, systemic pattern of
constitutional violations involving other individuals. Because his theory
of liability with respect to the City involves only actors below the policy-
making level, a showing of a systemic pattern of violations was a
necessary first step in making out a viable Monell claim. See Ricciuti v.
N.Y.C. Transit Auth., 941 F.2d 119, 123 (2d Cir. 1991). And, in any
event, his Monell claim against the City would independently fail based
on the absence of a underlying constitutional violation. See City of Los
Angeles v. Heller, 475 U.S. 796, 799 (1986). This Court should therefore
reject Portelos’s effort to revive his Monell claim against the City.
B. At trial, the district court correctly dismissed

Portelos’s Monell claim against the Department.
The district court also correctly dismissed Portelos’s Monell claim
against the Department. After making that ruling, the court correctly
rejected Portelos’s two attempts to reinstate the claim, once in a motion
for reconsideration and again in his post-trial motion.
45
At the close of evidence, the court correctly noted that Portelos
had failed to identify authority establishing that anyone other than
Chancellor Walcott was a policymaker with final decision-making
authority to suspend or bring disciplinary charges against Portelos (A.
862-63). Portelos’s theory had been that Superintendent Claudio’s
exercise of final decision-making authority violated his rights, but he
failed to cite authority or evidence demonstrating that Superintendent
Claudio’s recommendation to remove him was in fact a final decision (A.
862-65). As for Chancellor Walcott, Portelos had failed to present
evidence that Chancellor Walcott (or his designees) were aware that
Portelos had lodged allegations of timesheet fraud against Principal
Hill, so as to provide a motivation for retaliation (A. 862-65). Thus, the
court properly concluded that the Department could not be liable on a
Monell theory of liability (A. 865-66).
The court also did not err in denying Portelos’s improper motion to
reconsider the Court’s decision to dismiss the Department as a
defendant after closing arguments. In that motion for reconsideration,
Portelos for the first time cited Educ. Law § 2590-j as authority
establishing that Superintendent Claudio was a policymaker with final
46
decision-making authority, and cited evidence outside the trial record
purportedly showing that she had exercised this authority (A. 951-53).
But the court properly found that, even if Claudio was a final decision-
maker, Portelos’s assertion that she exercised this authority was based
upon evidence outside the trial record, and that Fed. R. Civ. Pro. 51
additionally barred him from making belated objections to the jury
instructions after summations (A. 952-53).
In any event, had the court considered Portelos’s non-record
evidence, it would not have changed the outcome of the trial. The jury
returned a verdict finding that Superintendent Claudio had not acted
with retaliatory intent, thus establishing that she did not a commit a
First Amendment violation to which any Monell liability could attach.
Accordingly, the court rightly determined that Portelos failed to
establish his entitlement to a new trial on his Monell claim against the
Department. Not only did the jury determine that Portelos did not
suffer an underlying constitutional violation (which alone would be
sufficient to defeat his Monell claim), but he also failed to demonstrate
the existence of a municipal policy or custom that caused any alleged
violation.
47
CONCLUSION
This Court should affirm the district court’s judgment.
Dated: New York, NY

June 7, 2017
Respectfully submitted,
ZACHARY W. CARTER
Corporation Counsel
of the City of New York
Attorney for Appellees
By: _/s/ Kathy C. Park_______

KATHY C. PARK
Assistant Corporation Counsel
100 Church Street

New York, New York 10007
212-356-0855
kpark@law.nyc.gov
SCOTT SHORR
KATHY C. PARK
of Counsel
48
CERTIFICATE OF COMPLIANCE
I hereby certify that this brief was prepared using Microsoft
Word 2010, and according to that software, it contains 9,036
words, not including the table of contents, table of authorities, this
certificate, and the cover.
______ /s/ Kathy C. Park _____

KATHY C. PARK
49

The Clown

Transféré par

Informations du document

Copyright

Formats disponibles

Partager ce document

Partager ou intégrer le document

Options de partage

Avez-vous trouvé ce document utile ?

Ce contenu est-il inapproprié ?

Droits d'auteur :

Formats disponibles

The Clown

Transféré par

Droits d'auteur :

Formats disponibles

Case 16-3932, Document 66, 06/12/2017, 2055620, Page1 of 56

LINDA HILL, Principal of I.S. 49, in her official and

DENNIS WALCOTT, Chancellor of New York City

On Appeal from the United States District Court

BRIEF FOR APPELLEES

Reproduced on Recycled Paper

TABLE OF AUTHORITIES .....................................................................iii

PRELIMINARY STATEMENT ................................................................. 1

ISSUES PRESENTED FOR REVIEW ..................................................... 5

STATEMENT OF THE CASE .................................................................. 6

A. Portelos’s history of lashing out in response to perceived

1. After Principal Hill declined to promote anyone to a

2. After a union leader asked him to curtail his union

3. After Principal Hill admonished him for misconduct,

4. After an investigation of his conduct began, Portelos

B. Portelos’s temporary removal from his teaching duties,

1. The partial grant of summary judgment to defendants....... 20

2. The jury verdict in defendants’ favor ................................... 22

3. The denial of Portelos’s new-trial motion ............................. 25

TABLE OF CONTENTS (cont’d)

STANDARD OF REVIEW AND SUMMARY OF ARGUMENT ............ 26

THE COURT AND THE JURY PROPERLY REJECTED

A. As a matter of law, when Portelos spoke in his capacity

B. As the district court properly determined, Portelos’s

C. The district court properly denied Portelos’s motion for a

THE DISTRICT COURT PROPERLY DISMISSED

A. On summary judgment, the district court correctly

B. At trial, the district court correctly dismissed Portelos’s

CERTIFICATE OF COMPLIANCE ........................................................ 49

Bd. of the Cnty. Comm’rs v. Brown,

Burkybile v. Bd. of Educ.,

City of Los Angeles v. Heller,

Ezekwo v. N.Y.C. Health & Hosps. Corp.,

Jones v. Town of East Haven,

TABLE OF AUTHORITIES (cont’d)

Monell v. Dep’t of Soc. Servs. of the City of New York,

New Phone Co., Inc. v. City of New York,

Niagara Mohawk Power Corp. v. Jones Chem., Inc.,

Ricciuti v. N.Y.C. Transit Auth.,

Roe v. City of Waterbury,

Saulpaugh v. Monroe Cmty. Hosp.,

Sequa Corp. v. GBJ Corp.,

Shrader v. CSX Transportation, Inc.,

SongByrd, Inc. v. Estate of Grossman,

TABLE OF AUTHORITIES (cont’d)

Velez v. City of New York,

Weintraub v. Bd. of Educ.,

42 U.S.C. § 1983 ............................................................................ 1, 19, 43

Educ. Law § 2590-j ............................................................................ 23, 46

Educ. Law § 3020-a ........................................................................... 36, 37

Civil Service Law § 75-b ........................................................ 18, 20, 21, 22

U.S. Const. amend. I ....................................................................... passim

Fed. R. App. Pro. 3(c)(1)(B) ....................................................................... 4

Fed. R. Civ. Pro. 12(b)(6) ......................................................................... 19

Fed. R. Civ. Pro. 50.................................................................................. 23

Fed. R. Civ. Pro. 51............................................................................ 24, 47

Fed. R. Civ. Pro. 59.......................................................................... passim

Local Civil Rule 6.3, Local Rules of the United States

TABLE OF AUTHORITIES (cont’d)

The Special Commissioner of Investigation, http://nycsci.org

United Federation of Teachers Collective Bargaining

Plaintiff-appellant Francesco Portelos, a tenured science and

technology teacher for the New York City Department of Education,

never hesitated to retaliate when an administrator or union leader took