Ruotolo v. City of New York ( 2008 )


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  • 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