Court Opinion

ID: 2960021
Source: CourtListenerOpinion
Date Created: 2015-09-17 17:39:00.174343+00
Date Added: 2024-06-11T11:59:47.958171
License: Public Domain

06-3886-cv
Ruotolo v. City of New York

 1                      UNITED STATES COURT OF APPEALS
 2                          FOR THE SECOND CIRCUIT
 3
 4                             August Term, 2007
 5
 6
 7    (Argued: September 25, 2007          Decided: February 6, 2008)
 8
 9                            Docket No. 06-3886-cv
10
11   - - - - - - - - - - - - - - - - - - - -X
12
13   ANGELO RUOTOLO,
14
15                   Plaintiff-Appellant,
16
17              - v.-
18
19   CITY OF NEW YORK; RAYMOND KELLY,
20   Commissioner of Police, City of New
21   York; PATRICK J. TIMLIN, Former Chief
22   of Police, City of New York, Bronx;
23   RAYMOND ROONEY, Deputy Inspector, New
24   York City Police Department, formerly
25   Commanding Officer 50th Precinct,
26   Bronx; WILLIAM RILEY, Lieutenant, New
27   York City Police Department, formerly
28   Integrity Control Officer, 50th
29   Precinct, Bronx,
30
31                   Defendants-Appellees.
32
33   - - - - - - - - - - - - - - - - - - - -X
34

35        Before:    JACOBS, Chief Judge, LEVAL and SOTOMAYOR,
36                   Circuit Judges.
37
38        Appeal from the judgment of the United States District
1    Court for the Southern District of New York (Stein, J.)

2    dismissing, under Fed. R. Civ. P. 12(b)(6), a police

3    officer’s claim that he was subjected to retaliation in

4    violation of his First Amendment rights for [i] writing an

5    official report about health concerns at his precinct, and

6    [ii] filing a lawsuit that challenged personnel action taken

7    against him in the wake of that report.    Also appealed is

8    the denial of leave to amend the complaint.

9        AFFIRMED.

10                                 ANDREW M. WONG, New York, NY,
11                                 for Plaintiff-Appellant.
12
13                                 TAHIRIH M. SADRIEH, Assistant
14                                 Corporation Counsel (Michael A.
15                                 Cardozo, Corporation Counsel for
16                                 the City of New York), New York,
17                                 NY, for Defendants-Appellees.
18
19   DENNIS JACOBS, Chief Judge:

20       Retired police sergeant Angelo Ruotolo (“Ruotolo”) sues

21   the City of New York (the “City”) and various officials and

22   members of the New York City Police Department

23   (collectively, the “NYPD”), alleging retaliation in

24   violation of the First Amendment for his speech regarding

25   health concerns at his precinct.    He appeals from a judgment

26   of the United States District Court for the Southern

27   District of New York (Stein, J.), granting defendants’

                                    2
1    motion to dismiss the “Second Amended and Supplemental

2    Complaint” (the “Complaint”) for failure to state a claim

3    under Fed. R. Civ. P. 12(b)(6).   Ruotolo’s speech consisted

4    of a report concerning health conditions at his precinct,

5    which he was directed to prepare in his role as precinct

6    Safety Officer, and a lawsuit he filed in the wake of

7    retaliatory personnel action taken against him after the

8    report was submitted.   The district court dismissed, citing

9    Garcetti v. Ceballos, 547 U.S. 410, 126 S. Ct. 1951 (2006),

10   on the ground that both the report and the lawsuit were

11   unprotected because Ruotolo was speaking as a public

12   employee in the course of his employment duties.     No appeal

13   is taken from the dismissal of the claim premised on

14   Ruotolo’s report.   As to Ruotolo’s lawsuit, we affirm on the

15   ground that it did not address a matter of public concern.

16   And we affirm the district court’s exercise of its

17   discretion to deny leave to amend the complaint based on

18   plaintiff’s delay and the undue burden and prejudice to

19   defendants.

20

21                            BACKGROUND

22       Ruotolo was an NYPD Sergeant with 20 years service when

                                   3
1    he retired in 2004.    In October 1999, Ruotolo was serving as

2    the Training and Safety Officer for the 50th Precinct in the

3    Bronx.     When a local newspaper reported possible

4    contamination and health risks at the precinct from

5    underground gasoline storage tanks, Ruotolo was assigned--in

6    his capacity as Safety Officer--to survey employee illnesses

7    and deaths that might be related to this potential

8    environmental hazard.     His two-page report, dated October

9    28, 1999 (the “October 1999 Report”), and titled “Survey

10   Pursuant to Request,” identified a seemingly large number of

11   cancers, miscarriages, birth defects and other health

12   problems afflicting individuals working at the precinct.

13   Ruotolo recommended a thorough environmental evaluation,

14   which was done.

15       The environmental experts reported that leakage from

16   the fuel storage tanks into the soil and air had raised

17   contaminant levels above OSHA and EPA safety standards.    At

18   great expense and over many months, the City undertook to

19   abate the hazard.     Representatives of the Patrolmen’s

20   Benevolent Association (“PBA”) came to the precinct in April

21   2000 to sign up potential plaintiffs for a personal injury

22   lawsuit.    One of the PBA lawyers asked to speak with Ruotolo

                                     4
1    because he was the author of the October 1999 Report.     As

2    Ruotolo testified in his March 2005 deposition in this

3    lawsuit, he answered the PBA’s questions with the knowledge

4    of his commanding officer, spoke to no one else about the

5    proposed lawsuit, did not himself enlist as a plaintiff, and

6    never learned whether an action was filed.   This encounter

7    was not pled in any version of Ruotolo’s complaint prior to

8    dismissal of the action, but it is relevant to our analysis.

9        Ruotolo alleges that he experienced on-the-job

10   retaliation starting soon after submitting the October 1999

11   Report to his commanding officer, and continuing until he

12   retired.   The retaliation included: frequent reassignments

13   to undesirable shifts and to duties he considered beneath

14   his rank and tenure, denial of use of leave time, transfer

15   to a less desirable precinct, and discipline for trivial or

16   fabricated reasons.   After Ruotolo alleged those acts of

17   retaliation (in the original complaint in this lawsuit,

18   filed in July 2003), Ruotolo alleged (in amended complaints)

19   that the retaliation took additional forms, including verbal

20   harassment by superior officers, denial of overtime

21   assignments, the first negative performance review of his

22   career, and excessive discipline for a minor infraction.

                                   5
1    As a result of that discipline, Ruotolo was put on “modified

2    duty,” and was stripped of his badge, shield, identification

3    card and weapons.    He was still on modified duty when he

4    retired on July 26, 2004, which meant he lost the privilege

5    of carrying a firearm after retirement (thus reducing his

6    prospect for future income in the security field).      Based on

7    these experiences, Ruotolo attributed to the City a

8    “municipal custom and practice of tolerance of the violation

9    of [whistle-blowers’] rights.”

10       As compensatory damages, Ruotolo alleges lost income

11   and reduced pension benefits.       Ruotolo also seeks punitive

12   damages, and an injunction to (i) expunge from his

13   employment records the retaliatory disciplinary charges and

14   performance reviews, and (ii) restore impaired retirement

15   benefits and privileges.

16       The original complaint identified the October 1999

17   Report as the single episode of speech underlying his First

18   Amendment claim.    Over the next three years of active

19   litigation, Ruotolo was twice given leave to amend his

20   complaint, notably to add the filing of his lawsuit as the

21   second--and only other--instance of speech for which Ruotolo

22   alleged retaliation.    By May 2006, the parties had concluded

                                     6
1    extensive discovery, narrowed the claims through multiple

2    dispositive motions (various state law claims were dismissed

3    on an earlier Rule 12(b)(6) motion), litigated numerous

4    discovery and trial-related motions, and submitted their

5    final joint pretrial order.

6        Trial on Ruotolo’s surviving claims was two weeks away

7    when the Supreme Court ruled in Garcetti v. Ceballos that

8    “when public employees make statements pursuant to their

9    official duties, the employees are not speaking as citizens

10   for First Amendment purposes, and the Constitution does not

11   insulate their communications from employer discipline.”

12   126 S. Ct. 1951, 1960 (2006).       Upon the defendants’ renewed

13   motion to dismiss, the district court ruled that the First

14   Amendment claim succumbed to Garcetti because Ruotolo

15   admittedly wrote the October 1999 Report in his capacity as

16   Safety Officer, and because the lawsuit was premised solely

17   on non-actionable speech.   As to the lawsuit, the court

18   explained:

19            After Garcetti, for a lawsuit adequately to charge
20            a First Amendment retaliation claim, the lawsuit
21            must be predicated on speech made by a public
22            employee as a citizen, and not pursuant to his or
23            her official duties. To hold otherwise--that
24            filing a lawsuit alleging retaliation for non-
25            protected speech would give rise to a First
26            Amendment complaint--would defy logic, allowing a

                                     7
1               plaintiff to bootstrap a non-actionable objection
2               to legitimate employer discipline into a valid
3               First Amendment claim.
4
5    (Emphasis in original).

6        In opposing the Rule 12(b)(6) motion, Ruotolo

7    unsuccessfully attempted to rehabilitate his Complaint by

8    reference to his deposition testimony about the April 2000

9    conversation with a PBA representative.    For the first time,

10   Ruotolo argued that he was not then speaking in his official

11   capacity as Safety Officer (and author of the October 1999

12   Report), but rather was speaking as a private citizen on a

13   health matter of public concern.   As Ruotolo had as yet

14   never alleged the April 2000 PBA conversation, the district

15   court decided that the exchange with the PBA was outside the

16   pleadings and not properly considered on a motion to

17   dismiss.

18       Final judgment was entered on July 21, 2006.    Ruotolo

19   moved to vacate the judgment and for leave to file a Third

20   Amended and Supplemental Complaint.   The district court

21   denied vacatur because Ruotolo “failed to demonstrate a need

22   to prevent manifest injustice or correct a clear error that

23   would affect the outcome of the case.”    The district court

24   also denied leave to amend to add the PBA conversation

                                    8
1    because of undue delay, and the undue burden and prejudice

2    that would result to defendants.     Ruotolo timely appealed

3    these rulings and the final judgment.

4

5                               DISCUSSION

6        We review de novo a district court’s dismissal of a

7    complaint pursuant to Rule 12(b)(6), “accepting all factual

8    allegations in the complaint and drawing all reasonable

9    inferences in the plaintiff’s favor.”    ATSI Commc’n, Inc. v.

10   Shaar Fund, Ltd., 493 F.3d 87, 98 (2d Cir. 2007).      To

11   survive a motion to dismiss, a complaint must plead “enough

12   facts to state a claim to relief that is plausible on its

13   face.”     Bell Atlantic Corp. v. Twombly, -- U.S. --, 127 S.

14   Ct. 1955, 1974 (2007).

15

16                                   A

17            On appeal, Ruotolo concedes that Garcetti mandates

18   dismissal of the First Amendment claim premised on the

19   October 1999 Report.     Ruotolo argues, however, that the

20   district court erred in reading Garcetti to require

21   dismissal of the claim premised on his filing a federal

22   lawsuit.    We hold that Ruotolo’s claim based on his lawsuit

                                     9
1    must fail because his lawsuit did not address a matter of

2    public concern.

3        Whether public employee speech is protected from

4    retaliation under the First Amendment entails two inquiries:

5    (1) “whether the employee spoke as a citizen on a matter of

6    public concern” and, if so, (2) “whether the relevant

7    government entity had an adequate justification for treating

8    the employee differently from any other member of the

9    general public.”   Garcetti, 126 S. Ct. at 1958 (citing

10   Pickering v. Bd. of Educ. of Township High Sch. Dist. 205,

11   Will County, 391 U.S. 563, 568 (1968)); see also Skehan v.

12   Vill. of Mamaroneck, 465 F.3d 96, 106 (2d Cir. 2006)

13   (rephrasing the test for a First Amendment retaliation claim

14   as three-pronged, requiring plaintiffs to prove: “(1) they

15   engaged in constitutionally protected speech because they

16   spoke as citizens on a matter of public concern; (2) they

17   suffered an adverse employment action; and (3) the speech

18   was a motivating factor in the adverse employment decision”

19   (internal quotation marks and citation omitted)). The

20   majority opinion in Garcetti focused on the first inquiry,

21   and specifically its operation as a limiting principle when

22   the government is acting as an employer, exercising control

                                   10
1    over employee speech in the interest of the “efficient

2    provision of public services.”     Garcetti, 126 S. Ct. at

3    1958.   Recognizing that government employers (like private

4    employers) “have heightened interests in controlling speech

5    made by an employee in his or her professional capacity,”

6    the Supreme Court ruled that a public employee speaking in

7    his official capacity is not speaking as a citizen for First

8    Amendment purposes, id. at 1960, and employer retaliation

9    for such speech does not justify the “displacement of

10   managerial discretion by judicial supervision,” id. at 1961.

11       The principal episode of speech at issue in Garcetti

12   was a memo in which a deputy district attorney alerted his

13   supervisors to perceived irregularities in how a search

14   warrant was obtained in a particular case.     In precluding

15   that First Amendment claim, the Court emphasized that the

16   memo was written as part of the employee’s official duties

17   and that the employer’s negative reaction to it “simply

18   reflects the exercise of employer control over what the

19   employer itself has commissioned or created.”     Id. at 1960.

20   The Garcetti plaintiff “did not act as a citizen when he

21   went about conducting his daily professional activities . .

22   . . When he went to work and performed the tasks he was paid

                                   11
1    to perform, [plaintiff] acted as a government employee.”

2    Id.   Similarly (as is undisputed here), Ruotolo prepared his

3    October 1999 Report as part of his official duties, and for

4    that reason Ruotolo has not appealed from this aspect of the

5    district court’s ruling.1

6          Ruotolo argues that his First Amendment retaliation

7    claim nonetheless survives as to damages arising out of

8    post-lawsuit retaliation, because this lawsuit was filed in

9    his capacity as a private citizen.   The district court

10   rejected this argument, holding that under Garcetti, the

11   First Amendment does not protect a government employee from

12   retaliation for filing a lawsuit in which the underlying

13   retaliation claim rests on non-actionable official speech.

14   We need not decide whether Ruotolo’s lawsuit amounts to

15   speech by a “citizen” rather than by a “public employee”

16   within the meaning of Garcetti: a simpler ground is

17   available because in any event that speech is not “on a

           1
           As the Garcetti Court observed, public employees who
     suffer retaliation for their official speech are not without
     recourse, and should avail themselves of the “powerful
     network of legislative enactments--such as whistle-blower
     protection laws and labor codes--available to those who seek
     to expose wrongdoing.” Garcetti, 126 S. Ct. at 1962. We
     express no opinion as to the availability of such recourse
     to Ruotolo.

                                   12
1    matter of public concern.”   Id. at 1958.

2        “Whether an employee’s speech addresses a matter of

3    public concern is a question of law for the court to decide,

4    taking into account the content, form, and context of a

5    given statement as revealed by the whole record.”    Lewis v.

6    Cowen, 165 F.3d 154, 163 (2d Cir. 1999) (citing Connick v.

7    Myers, 461 U.S. 138, 147-48 and n.7 (1983)).    The heart of

8    the matter is whether the employee’s speech was “calculated

9    to redress personal grievances or whether it had a broader

10   public purpose.”   Lewis, 165 F.3d at 163-64.   Ruotolo’s

11   lawsuit sought to redress his personal grievances.    It did

12   not seek to advance a public purpose.   We therefore hold

13   that his lawsuit did not constitute speech on a matter of

14   public concern, and we affirm the district court’s dismissal

15   on that basis.

16       As to the personal nature of Ruotolo’s grievances, the

17   Complaint alleges that Ruotolo wrote the October 1999 Report

18   because he was assigned to do so as part of his job, and

19   that the Report led to retaliatory acts affecting Ruotolo

20   alone.   The acts of alleged retaliation against Ruotolo bear

21   upon the circumstances and perquisites of his employment,

22   such as reassignment, transfer, time off, and discipline.

                                   13
1    The section of the Complaint titled “Consequences of the

2    Retaliation” enumerates adverse career, financial and

3    emotional effects that Ruotolo suffered personally.     The

4    relief sought is also almost entirely personal to Ruotolo,

5    including compensatory damages and an injunction relating to

6    Ruotolo’s employment records.

7        The Complaint accuses the City of routinely tolerating

8    the violation of whistleblower rights, and seeks punitive

9    damages to deter “future illegal and retaliatory conduct,”

10   arguably hinting at some broader public purpose.     However,

11   retaliation against the airing of generally personal

12   grievances is not brought within the protection of the First

13   Amendment by “the mere fact that one or two of [a public

14   employee’s] comments could be construed broadly to implicate

15   matters of public concern.”     Ezekwo v. New York City Health

16   & Hosp. Corp., 940 F.2d 775, 781 (2d Cir. 1991).

17        In Ezekwo, a physician complained about aspects of her

18   hospital residency program, including unfair evaluation of

19   her by attending physicians, the lack of opportunity to

20   perform surgery and learn specialized skills, and

21   discrimination on the basis of race, sex and national

22   origin.   She also complained generally about the attending

                                     14
1    physicians’ poor management skills and teaching methods,

2    their lack of punctuality, and the lack of proper hospital

3    maintenance.   Viewing these complaints “objectively and as a

4    whole,” we held that, for First Amendment purposes, these

5    complaints were not matters of public concern.   Id.

6    Although the quality of a physician-training program may

7    affect the public, we concluded that the plaintiff “was not

8    on a mission to protect the public welfare.   Rather her

9    primary aim was to protect her own reputation and individual

10   development as a doctor.”   Id.; see also Tiltti v. Weise,

11   155 F.3d 596, 603 (2d Cir. 1998) (finding no public concern

12   in complaints about working conditions made by customs

13   officers who alleged retaliation when they were reassigned,

14   despite their claim that the relocations would adversely

15   affect homeland security); Cotarelo v. Vill. of Sleepy

16   Hollow Police Dep’t, 460 F.3d 247, 252 (2d Cir. 2006)

17   (finding police officer’s lawsuit is a matter of public

18   concern because his allegations concerned “discrimination

19   problems generally and were not limited to instances

20   affecting only [the plaintiff].”).

21       As the Eleventh Circuit observed, “[a] public employee

22   may not transform a personal grievance into a matter of

                                   15
1    public concern by invoking a supposed popular interest in

2    the way public institutions are run.”    Boyce v. Andrew, 510

3    F.3d 1333, 1343 (11th Cir. 2007) (quoting Ferrara v. Mills,

4    781 F.2d 1508, 1516 (11th Cir. 1986)).    A generalized public

5    interest in the fair or proper treatment of public employees

6    is not enough.   Because Ruotolo’s lawsuit concerns

7    essentially personal grievances and the relief he seeks is

8    for himself alone, the lawsuit is not speech on a matter of

9    public concern and cannot sustain a First Amendment

10   retaliation claim.

11

12                                 B

13       After final judgment was entered dismissing the

14   Complaint, Ruotolo moved to vacate the judgment and file a

15   Third Amended and Supplemental Complaint.    Thus Ruotolo

16   sought to plead another instance of speech that would not be

17   vulnerable to the specific Garcetti analysis that had

18   defeated the claim premised on the October 1999 Report.     The

19   proposed amended pleading frames Ruotolo’s April 2000

20   conversation with PBA representatives as an episode of

21   protected speech made in his capacity as a private citizen.

22   A denial of a motion to vacate a judgment under Rule 60(b)

                                   16
1    is reviewed for abuse of discretion, see Transaero, Inc. v.

2    La Fuerza Aerea Boliviana, 162 F.3d 724, 729 (2d Cir. 1998),

3    likewise, a denial of leave to amend a complaint under Rule

4    15(a), see Ruffolo v. Oppenheimer & Co., 987 F.2d 129, 131

5    (2d Cir. 1993) (per curiam).

6        A party seeking to file an amended complaint post-

7    judgment must first have the judgment vacated or set aside

8    pursuant to Fed. R. Civ. P. 59(e) or 60(b).   See Nat’l

9    Petrochemical Co. of Iran v. M/T Stolt Sheaf, 930 F.2d 240,

10   244-45 (2d Cir. 1991) (noting that Rule 15(a)’s liberal

11   amendment policy should not “be employed in a way that is

12   contrary to the philosophy favoring finality of judgments

13   and the expeditious termination of litigation” (internal

14   quotation marks and citation omitted)).    Ruotolo moved to

15   set aside the judgment pursuant to Rule 60(b), a mechanism

16   for “extraordinary judicial relief” invoked only if the

17   moving party demonstrates “exceptional circumstances.”

18   Paddington Partners v. Bouchard, 34 F.3d 1132, 1142 (2d Cir.

19   1994) (citation omitted).   The district court found no such

20   “exceptional circumstances,” and Ruotolo’s appeal does not

21   press for relief on that ground.    Nor does there appear to

22   be a basis for Rule 60(b) relief.    Therefore, ordinarily “it

                                    17
1    would be contradictory to entertain a motion to amend the

2    complaint.”    Nat’l Petrochemical Co. of Iran, 930 F.2d at

3    245.    However, we have said in dicta that “in view of the

4    provision in rule 15(a) that ‘leave [to amend] shall be

5    freely given when justice so requires,’ it might be

6    appropriate in a proper case to take into account the nature

7    of the proposed amendment in deciding whether to vacate the

8    previously entered judgment.”        Id. (citing Foman v. Davis,

9    371 U.S. 178, 182 (1962)).    Even assuming that a post-

10   judgment motion to amend can be heard, we see no basis for

11   finding any abuse of discretion here.

12          Leave to amend, though liberally granted, may properly

13   be denied for:    “undue delay, bad faith or dilatory motive

14   on the part of the movant, repeated failure to cure

15   deficiencies by amendments previously allowed, undue

16   prejudice to the opposing party by virtue of allowance of

17   the amendment, futility of amendment, etc.”       Foman, 371 U.S.

18   at 182.    “Mere delay, however, absent a showing of bad faith

19   or undue prejudice, does not provide a basis for the

20   district court to deny the right to amend.”       State Teachers

21   Ret. Bd. v. Fluor Corp., 654 F.2d 843, 856 (2d Cir. 1981);

22   see also 6 Charles Allen Wright, Arthur R. Miller & Mary Kay

                                     18
1    Kane, Federal Practice and Procedure: Civil 2d, § 1487, at

2    613 (1990 & 2007 Supp.) (citing prejudice to the opposing

3    party as “the most important factor” and “the most frequent

4    reason for denying leave to amend”).        In denying Rule 15(a)

5    relief, the district court found that Ruotolo’s delay in

6    seeking leave to amend was inexcusable given the previous

7    opportunities to amend, and the defendants’ burden and

8    prejudice.    These findings were well within the bounds of

9    its discretion.

10       When the original complaint was filed in 2003, Ruotolo

11   certainly knew about his own conversation with the PBA back

12   in 2000.     Ruotolo seeks to excuse his delay in pleading this

13   conversation on the ground that he did not realize its

14   significance until the Supreme Court spoke in Garcetti.

15   True, Ruotolo was not required to plead every conversation

16   he had as a private citizen; but he may be expected to have

17   pled every such conversation as to which he was asserting

18   unconstitutional retaliation.        Nothing in the law pre-

19   Garcetti prevented or inhibited him from pleading the PBA

20   conversation.    Even after Ruotolo testified about it at his

21   March 2005 deposition, he evidently did not believe that he

22   suffered unconstitutional retaliation on that account, and

                                     19
1    therefore did not mention it in his Second Amended and

2    Supplemental Complaint filed in August 2005.   “When the

3    moving party has had an opportunity to assert the amendment

4    earlier, but has waited until after judgment before

5    requesting leave, a court may exercise its discretion more

6    exactingly.”    State Trading Corp. of India, Ltd. v.

7    Assuranceforeningen Skuld, 921 F.2d 409, 418 (2d Cir. 1990)

8    (denying leave to amend complaint to plead additional causes

9    of action based on foreign law long known to movant).

10       In gauging prejudice, we consider, among other factors,

11   whether an amendment would “require the opponent to expend

12   significant additional resources to conduct discovery and

13   prepare for trial” or “significantly delay the resolution of

14   the dispute.”   Block v. First Blood Assocs., 988 F.2d 344,

15   350 (2d Cir. 1993).   Undue prejudice arises when an

16   “amendment [comes] on the eve of trial and would result in

17   new problems of proof.”   Fluor Corp., 654 F.2d at 856

18   (reversing denial of leave to amend sought promptly after

19   learning new facts, where “no trial date had been set by the

20   court and no motion for summary judgment had yet been filed

21   by the defendants” and where “the amendment will not involve

22   a great deal of additional discovery”).

                                    20
1        Ruotolo argues that he should not be faulted for his

2    delay in seeking to amend his complaint prior to the

3    Garcetti decision because prior to Garcetti he had no good

4    reason to do so.   We need not decide what would be the force

5    of this argument because Ruotolo did not move promptly

6    following the Garcetti decision, when the vulnerability of

7    his complaint became evident.        Ruotolo waited until after

8    the district court dismissed his complaint to propose an

9    amendment.

10       Ruotolo’s proposed amendment comes post-judgment in a

11   case that had been trial-ready, and pleads a new scenario

12   that would prevent disposition of the case until either

13   further motion practice or a trial--and any trial or motion

14   practice would likely be delayed pending discovery on open

15   questions.   Did Ruotolo participate in the PBA conversation

16   in his official capacity?   Who said what?      Did that

17   conversation provoke retaliation?        Can that retaliation be

18   teased apart from the retaliation allegedly premised on the

19   October 1999 Report?   Because the proposed amendment would

20   unduly burden and prejudice defendants in the circumstances

21   of this case, it is properly barred.        See Bradick v. Israel,

22   377 F.2d 262, 263 (2d Cir. 1967) (per curiam) (affirming

                                     21
1    denial of motion to amend brought on eve of trial, adding

2    new theories of law and new problems of proof); 6 Wright,

3    Miller & Kane, § 1487, at 623 and n.9 (amendment is

4    prejudicial when it “substantially changes the theory on

5    which the case has been proceeding and is proposed late

6    enough so that the opponent would be required to engage in

7    significant new preparation”).     We therefore see no ground

8    for vacatur or other post-judgment relief.

9

10                                 C

11       Ruotolo’s remaining arguments pertain to his due

12   process claim and the New York State whistle-blower

13   protection statute.   Those claims are not properly before us

14   because they were raised for the first time on appeal.     See

15   Bogle-Assegai v. Connecticut, 470 F.3d 498, 504 (2d Cir.

16   2006).

17

18                            CONCLUSION

19       For the foregoing reasons, the judgment of the district

20   court is affirmed.

                                   22