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@[Link]
June 7, 2017

Reproduced on Recycled Paper

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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

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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

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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

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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

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TABLE OF AUTHORITIES (cont’d)

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

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TABLE OF AUTHORITIES (cont’d)

Page(s)

The Special Commissioner of Investigation, [Link]

(last visited Jun. 7, 2017) ................................................................... 14

United Federation of Teachers Collective Bargaining

Agreement, Art. 21(G)(8), [Link] (last
visited Jun. 7, 2017) ............................................................................ 37

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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
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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

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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

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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).

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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

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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 [Link], separate

from the Department’s official website, for the school’s use (A. 601).

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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 [Link] 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).

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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.

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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

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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).

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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 [Link] 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

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he could not access his [Link] 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).

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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 [Link] 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

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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, [Link] (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).

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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 [Link] (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).

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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

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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

[Link], which was an expired website initially

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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, [Link], 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

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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 [Link] 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

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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

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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

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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.

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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

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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

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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).

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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

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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.

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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

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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

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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

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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

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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

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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).

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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.

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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).

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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

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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, [Link] (last visited Jun. 7, 2017).

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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

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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

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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

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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

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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.

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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

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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.

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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.

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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

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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.

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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@[Link]
SCOTT SHORR
KATHY C. PARK
of Counsel

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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

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