24-2051-cv Caraballo v. City of New York et al.
UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT
SUMMARY ORDER RULINGS BY SUMMARY ORDER DO NOT HAVE PRECEDENTIAL EFFECT. CITATION TO A SUMMARY ORDER FILED ON OR AFTER JANUARY 1, 2007, IS PERMITTED AND IS GOVERNED BY FEDERAL RULE OF APPELLATE PROCEDURE 32.1 AND THIS COURT’S LOCAL RULE 32.1.1. WHEN CITING A SUMMARY ORDER IN A DOCUMENT FILED WITH THIS COURT, A PARTY MUST CITE EITHER THE FEDERAL APPENDIX OR AN ELECTRONIC DATABASE (WITH THE NOTATION “SUMMARY ORDER”). A PARTY CITING A SUMMARY ORDER MUST SERVE A COPY OF IT ON ANY PARTY NOT REPRESENTED BY COUNSEL.
At a stated term of the United States Court of Appeals for the Second Circuit, held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, on the 19th day of May, two thousand twenty-five.
PRESENT: REENA RAGGI, SUSAN L. CARNEY, ALISON J. NATHAN, Circuit Judges. ___________________________________________
Thomas Caraballo,
Plaintiff-Appellant,
v. No. 24-2051-cv
City of New York, Detective Kaiser Surriga, Detective Wayne Costello, Detective Robert DiFalco, Defendants-Appellees. * ___________________________________________
FOR PLAINTIFF-APPELLANT: Brian J. Isaac, Kenneth J. Gorman, Pollack, Pollack, Isaac & DeCicco, LLP, New York, NY.
FOR DEFENDANTS-APPELLEES: Richard Dearing, Doborah A. Brenner, Geoffrey E. Curfman, of Counsel, Muriel Goode-Trufant, Corporation Counsel of the City of New York, New York, NY.
Appeal from a judgment of the United States District Court for the Eastern
District of New York (Ross, Judge).
UPON DUE CONSIDERATION, IT IS HEREBY ORDERED,
ADJUDGED, AND DECREED that the August 2, 2024 judgment is AFFIRMED.
Thomas Caraballo sued the City of New York and three of its employees,
Detectives Kaiser Surriga, Wayne Costello, and Robert DiFalco, in January 2021
under 42 U.S.C. § 1983 in the Eastern District of New York for claims arising out of
a January 2019 arrest. While discovery was being conducted, Caraballo filed a
notice of claim against the City of New York in state small claims court. The City
and Caraballo settled that case and, in that process, executed, among other things,
* The Clerk of Court is respectfully directed to amend the official case caption as set forth above. 2 a General Release, pursuant to which, in exchange for $1,816.86, “Carabello [sic] .
. . release[d] and forever discharge[d] the City of New York, and all past and
present officers, directors, managers, administrators, employees, agents,
assignees, lessees, and representatives of the City of New York . . . from any and
all state and federal tort claims, causes of action, suits, occurrences, and damages,
whatsoever, known or unknown, including but not limited to state and federal
civil rights claims, actions, and damages, which” Caraballo “had, now has, or
hereafter can, shall, or may have, either directly or through subrogees or other
third persons . . . upon or by reason of any matter, cause, or thing whatsoever that
occurred through the date of” the release. App’x at 22.
Later, in federal court, the City and the Detectives filed a motion for
summary judgment, but did not raise the General Release as a defense. The
District Court granted the motion in part, among other things, dismissing
Caraballo’s claims against the City entirely. On July 2, 2024, however, the
Detectives moved to hold a pre-motion conference regarding an anticipated
second motion for summary judgment pursuant to the General Release, which the
Detectives’ attorney averred to having just discovered while preparing a list of
impeachment exhibits. Over Caraballo’s objection, the District Court considered
3 the second motion for summary judgment, which it granted. Caraballo timely
appealed. We assume the parties’ familiarity with the other relevant facts,
procedural history, and issues on appeal.
As a preliminary matter, we conclude that the District Court did not abuse
its discretion in permitting a second motion for summary judgment. “[D]istrict
courts enjoy considerable discretion in entertaining successive dispositive
motions.” Sira v. Morton, 380 F.3d 57, 68 (2d Cir. 2004). We have held that it may
be an abuse of discretion to permit a second dispositive motion if the arguments
in the second motion could have been brought into the first. Brown v. City of
Syracuse, 673 F.3d 141, 147 n.2 (2d Cir. 2012). But here the discovery of the General
Release meant “Appellees had reason to move again for summary judgment[.]” Id.
And insofar as the City was on notice of the General Release the moment it was
signed, it is unclear why the Detectives—who were the only defendants remaining
in the suit by this point—were. Given these circumstances, it was no abuse of
discretion to permit a second motion for summary judgment.
We turn to the merits and conclude that the District Court did not err in
granting summary judgment in light of the release.
Under New York law, “a written agreement that is complete, clear and
4 unambiguous on its face must be enforced according to the plain meaning of its
terms[.]” Greenfield v. Philles Recs., Inc., 98 N.Y.2d 562, 569 (2002). When
determining whether a contract is ambiguous, “language should not be read in
isolation because the contract must be considered as a whole[.]” Brad H. v. City of
New York, 17 N.Y.3d 180, 185 (2011). We agree with the District Court that the
General Release is not ambiguous as a matter of New York law and that its plain
terms release the Detectives from this suit.
Here, the General Release “release[d] and forever discharge[d] the City of
New York, and all past and present . . . employees . . . of the City of New York . . .
from any and all state and federal tort claims, causes of action, suits, occurrences,
and damages, whatsoever, known or unknown, including but not limited to state
and federal civil rights claims, actions, and damages, which” Caraballo “had, now
has, or hereafter can, shall, or may have, either directly or through subrogees or
other third persons . . . upon or by reason of any matter, cause, or thing whatsoever
that occurred through the date of” the release. App’x at 22. We have had several
occasions to interpret virtually identical language in general releases crafted by
the City of New York. Each time, we have summarily affirmed the grant of a
dispositive motion where claims in one action were released based on a general
5 release signed in a separate action. See Mateo v. Carinha. 799 F. App’x 51, 52–54
(2d Cir. 2020), Valdiviezo v. Greer, 787 F. App’x 48 (2d Cir. 2019); Walker v. Corizon,
764 F. App’x 78 (2d Cir. 2019); Fernandez v. City of New York, 502 F. App’x 48 (2d
Cir. 2012); Tromp v. City of New York, 465 F. App’x 50 (2d Cir. 2012)). New York’s
courts have reached similar results. Smith v. City of New York, 236 A.D.3d 414, 416
(1st Dep’t 2025). It is undisputed that the arrest giving rise to the underlying
claims occurred before the signing of the release. It is also undisputed that the
underlying claims are federal civil rights claims. And it is also undisputed that the
Detectives are New York City employees.
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24-2051-cv Caraballo v. City of New York et al.
UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT
SUMMARY ORDER RULINGS BY SUMMARY ORDER DO NOT HAVE PRECEDENTIAL EFFECT. CITATION TO A SUMMARY ORDER FILED ON OR AFTER JANUARY 1, 2007, IS PERMITTED AND IS GOVERNED BY FEDERAL RULE OF APPELLATE PROCEDURE 32.1 AND THIS COURT’S LOCAL RULE 32.1.1. WHEN CITING A SUMMARY ORDER IN A DOCUMENT FILED WITH THIS COURT, A PARTY MUST CITE EITHER THE FEDERAL APPENDIX OR AN ELECTRONIC DATABASE (WITH THE NOTATION “SUMMARY ORDER”). A PARTY CITING A SUMMARY ORDER MUST SERVE A COPY OF IT ON ANY PARTY NOT REPRESENTED BY COUNSEL.
At a stated term of the United States Court of Appeals for the Second Circuit, held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, on the 19th day of May, two thousand twenty-five.
PRESENT: REENA RAGGI, SUSAN L. CARNEY, ALISON J. NATHAN, Circuit Judges. ___________________________________________
Thomas Caraballo,
Plaintiff-Appellant,
v. No. 24-2051-cv
City of New York, Detective Kaiser Surriga, Detective Wayne Costello, Detective Robert DiFalco, Defendants-Appellees. * ___________________________________________
FOR PLAINTIFF-APPELLANT: Brian J. Isaac, Kenneth J. Gorman, Pollack, Pollack, Isaac & DeCicco, LLP, New York, NY.
FOR DEFENDANTS-APPELLEES: Richard Dearing, Doborah A. Brenner, Geoffrey E. Curfman, of Counsel, Muriel Goode-Trufant, Corporation Counsel of the City of New York, New York, NY.
Appeal from a judgment of the United States District Court for the Eastern
District of New York (Ross, Judge).
UPON DUE CONSIDERATION, IT IS HEREBY ORDERED,
ADJUDGED, AND DECREED that the August 2, 2024 judgment is AFFIRMED.
Thomas Caraballo sued the City of New York and three of its employees,
Detectives Kaiser Surriga, Wayne Costello, and Robert DiFalco, in January 2021
under 42 U.S.C. § 1983 in the Eastern District of New York for claims arising out of
a January 2019 arrest. While discovery was being conducted, Caraballo filed a
notice of claim against the City of New York in state small claims court. The City
and Caraballo settled that case and, in that process, executed, among other things,
* The Clerk of Court is respectfully directed to amend the official case caption as set forth above. 2 a General Release, pursuant to which, in exchange for $1,816.86, “Carabello [sic] .
. . release[d] and forever discharge[d] the City of New York, and all past and
present officers, directors, managers, administrators, employees, agents,
assignees, lessees, and representatives of the City of New York . . . from any and
all state and federal tort claims, causes of action, suits, occurrences, and damages,
whatsoever, known or unknown, including but not limited to state and federal
civil rights claims, actions, and damages, which” Caraballo “had, now has, or
hereafter can, shall, or may have, either directly or through subrogees or other
third persons . . . upon or by reason of any matter, cause, or thing whatsoever that
occurred through the date of” the release. App’x at 22.
Later, in federal court, the City and the Detectives filed a motion for
summary judgment, but did not raise the General Release as a defense. The
District Court granted the motion in part, among other things, dismissing
Caraballo’s claims against the City entirely. On July 2, 2024, however, the
Detectives moved to hold a pre-motion conference regarding an anticipated
second motion for summary judgment pursuant to the General Release, which the
Detectives’ attorney averred to having just discovered while preparing a list of
impeachment exhibits. Over Caraballo’s objection, the District Court considered
3 the second motion for summary judgment, which it granted. Caraballo timely
appealed. We assume the parties’ familiarity with the other relevant facts,
procedural history, and issues on appeal.
As a preliminary matter, we conclude that the District Court did not abuse
its discretion in permitting a second motion for summary judgment. “[D]istrict
courts enjoy considerable discretion in entertaining successive dispositive
motions.” Sira v. Morton, 380 F.3d 57, 68 (2d Cir. 2004). We have held that it may
be an abuse of discretion to permit a second dispositive motion if the arguments
in the second motion could have been brought into the first. Brown v. City of
Syracuse, 673 F.3d 141, 147 n.2 (2d Cir. 2012). But here the discovery of the General
Release meant “Appellees had reason to move again for summary judgment[.]” Id.
And insofar as the City was on notice of the General Release the moment it was
signed, it is unclear why the Detectives—who were the only defendants remaining
in the suit by this point—were. Given these circumstances, it was no abuse of
discretion to permit a second motion for summary judgment.
We turn to the merits and conclude that the District Court did not err in
granting summary judgment in light of the release.
Under New York law, “a written agreement that is complete, clear and
4 unambiguous on its face must be enforced according to the plain meaning of its
terms[.]” Greenfield v. Philles Recs., Inc., 98 N.Y.2d 562, 569 (2002). When
determining whether a contract is ambiguous, “language should not be read in
isolation because the contract must be considered as a whole[.]” Brad H. v. City of
New York, 17 N.Y.3d 180, 185 (2011). We agree with the District Court that the
General Release is not ambiguous as a matter of New York law and that its plain
terms release the Detectives from this suit.
Here, the General Release “release[d] and forever discharge[d] the City of
New York, and all past and present . . . employees . . . of the City of New York . . .
from any and all state and federal tort claims, causes of action, suits, occurrences,
and damages, whatsoever, known or unknown, including but not limited to state
and federal civil rights claims, actions, and damages, which” Caraballo “had, now
has, or hereafter can, shall, or may have, either directly or through subrogees or
other third persons . . . upon or by reason of any matter, cause, or thing whatsoever
that occurred through the date of” the release. App’x at 22. We have had several
occasions to interpret virtually identical language in general releases crafted by
the City of New York. Each time, we have summarily affirmed the grant of a
dispositive motion where claims in one action were released based on a general
5 release signed in a separate action. See Mateo v. Carinha. 799 F. App’x 51, 52–54
(2d Cir. 2020), Valdiviezo v. Greer, 787 F. App’x 48 (2d Cir. 2019); Walker v. Corizon,
764 F. App’x 78 (2d Cir. 2019); Fernandez v. City of New York, 502 F. App’x 48 (2d
Cir. 2012); Tromp v. City of New York, 465 F. App’x 50 (2d Cir. 2012)). New York’s
courts have reached similar results. Smith v. City of New York, 236 A.D.3d 414, 416
(1st Dep’t 2025). It is undisputed that the arrest giving rise to the underlying
claims occurred before the signing of the release. It is also undisputed that the
underlying claims are federal civil rights claims. And it is also undisputed that the
Detectives are New York City employees.
Many of Caraballo’s arguments venture beyond the writing’s four corners.
But under New York law, we are obliged to consider only intrinsic evidence of
ambiguity. Brad H., 17 N.Y.3d at 186. The primary such evidence Caraballo raises
is the General Release’s subtitle: “Property Damage Case.” App’x at 22. This does
not make the contract reasonably susceptible to Caraballo’s preferred
interpretation. This subtitle merely points to which case is being settled. Read in
context, there is no reason think the subtitle circumscribes the general language of
the General Release. Similarly, Caraballo points to the portion of the document
that describes the releasor as “Thomas Carabello [sic], the plaintiff in the action
6 entitled Thomas Carabello vs. The City of New York, Civil Court, Queens County”
and includes the index number of that case. App’x at 22. The inclusion of this
caption in the text of the Release does not change the result: in context, it is plainly
meant to identify Caraballo as the releasor, not to limit the scope of the release. In
light of the unambiguous text of the General Release, the District Court did not err
in granting summary judgment in favor of the Defendants.
Especially given that Caraballo was pro se in reviewing and signing the
General Release, we fully understand that he might not have actually understood
it to cover his pending federal claims. Nonetheless, New York law proscribes such
considerations. LeMay v. H.W. Keeney, Inc., 508 N.Y.S.2d 769, 770 (4th Dep’t 1986)
(“Where, as here, the language of a release is clear, effect will be given to the
intention of the parties as indicated by the language employed and the fact that
one of the parties may have intended something else is irrelevant.”).
We have considered Caraballo’s remaining arguments and conclude they
are without merit. Accordingly, we AFFIRM the judgment of the District Court.
FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court