Trapani v. Sypniewski et al

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UNITED STATES DISTRICT COURT
NORTHERN DISTRICT OF NEW YORK
DAMIAN R. TRAPANI,
Plaintiff,
1:25-CV-1846
v. 	(LEK/DJS)
MATTHEW J. SYPNIEWSKI, Schenectady County
Court Judge, et al.,
Defendants.
APPEARANCES:
DAMIAN R. TRAPANI
Plaintiff, Pro Se
Geneva, New York 14456
DANIEL J. STEWART
United States Magistrate Judge
REPORT-RECOMMENDATION and ORDER1
Plaintiff filed the Complaint on December 29, 2025. 	Dkt. No. 1. 	An Amended
Complaint was then filed on January 16, 2026, Dkt. No. 2, and a Second Amended
Complaint on January 27, 2026. Dkt. No. 3, Sec. Am. Compl. Consistent with the special
solicitude to be afforded pro se parties, and the Court’s broad discretion under FED . R.
CIV . P. 15(a)(2), the Court deems the Second Amended Complaint the operative pleading.
1 This matter was referred to the undersigned pursuant to L.R. 72.3(d).
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Plaintiff has also filed an application to proceed in forma pauperis, Dkt. No. 4, which was
granted by separate order.
The Complaint before the Court is 79 pages in length. It consists of 952 numbered
paragraphs and contains 64 causes of action. 	Over two dozen identified individuals or
entities are specifically named, and more than ten John Does are named as Defendants in
the action. 	While the Complaint was originally filed in December 2025, it contains
allegations dating back as far as April 2019. 	Many of the allegations made here mirror
those that were previously dismissed in Trapani v. Sypniewski, 23-CV-1433 (N.D.N.Y.).
The Court notes additionally that Plaintiff is a frequent litigator in this District, having
filed several other cases. Trapani v. Carney, 10-CV-1353; Trapani v. Bonafede, 14-CV-
556; Trapani v. Cuomo, 14-CV-683; Trapani v. Dagostino, 18-CV-805; Trapani v.
Annucci, 21-CV-681; Trapani v. St. Peters Hospital of the City of Albany, 25-CV-1479.
Rule 8 of the Federal Rules of Civil Procedure provides that a pleading must
contain:
(1) a short and plain statement of the grounds for the court’s jurisdiction . .
. ;
(2) a short and plain statement of the claim showing that the pleader is
entitled to relief; and
(3) a demand for the relief sought, which may include relief in the
alternative or different types of relief.
F ED . R. CIV . P. 8(a). Rule 8 serves “to give fair notice of the claim being asserted so as
to permit the adverse party the opportunity to file a responsive answer [and] prepare an
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adequate defense.” Powell v. Marine Midland Bank, 162 F.R.D. 15, 16 (N.D.N.Y. 1995)
(citation omitted). 	A complaint that fails to comply with basic pleading requirements
presents too heavy a burden for defendants to craft a defense “and provides no meaningful
basis for the Court to assess the sufficiency of [the plaintiff’s] claims,” and may properly
be dismissed. Gonzales v. Wing, 167 F.R.D. 352, 355 (N.D.N.Y. 1996).
“While ‘a court is obliged to construe pro se pleadings liberally, particularly when
they allege civil rights violations,’ McEachin v. McGuinnis, 357 F.3d 197, 200 (2d
Cir.2004), even pleadings submitted pro se must meet the notice requirements of Rule 8
of the Federal Rules of Civil Procedure.” 	West v. Goord, 2012 WL 1161508, at *3
(W.D.N.Y. Feb. 15, 2012) (internal alterations omitted), report and recommendation
adopted, 2012 WL 1161438 (W.D.N.Y. Apr. 6, 2012); see also Gunter v. Carrion, 2009
WL 10709657, at *1 (E.D.N.Y. Oct. 20, 2009) (noting that pro se litigants are “not
excused . . . from complying with the Federal Rules of Civil Procedure.”).
“It is well within the Court’s discretion to dismiss the pleading pursuant to Rule 8
for its length alone.” 	Rubin v. New York City Bd. of Educ., 2023 WL 1972729, at *9
(S.D.N.Y. Jan. 6, 2023), report and recommendation adopted, 2023 WL 2344731
(S.D.N.Y. Mar. 3, 2023) (citing cases). The Second Circuit has noted repeatedly that a
court can dismiss a claim under Rule 8 based on its length and lack of clarity. Blakely v.
Wells, 209 F. App’x 18, 20 (2d Cir. 2006); Owens v. McCall, 5 F. App’x 15, 16 (2d Cir.
2001). 	In Salahuddin v. Cuomo, the Second Circuit warned that “unnecessary prolixity
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in a pleading places an unjustified burden on the court and the party who must respond to
it because they are forced to select the relevant material from a mass of verbiage.”
Salahuddin v. Cuomo, 861 F.2d 40, 42 (2d Cir. 1988). Here, as noted above, the operative
pleading is anything but short. Apart from being verbose, it is also unclear in that many
of the allegations are undated and many of the causes of action do not specifically identify
the conduct giving rise to the claims. See, e.g., Sec. Am. Compl. at ¶¶ 664-680. This is
particularly problematic given the fact that the allegations in the pleading date back as far
as 2019 and many of the claims, therefore, would be subject to dismissal based on the
applicable three year statute of limitations for claims under 42 U.S.C. § 1983. Murphy v.
Lynn, 53 F.3d 547, 548 (2d Cir. 1995).
Here, while Plaintiff may be able to state a viable claim for relief, the nature of
Plaintiff’s Complaint makes that impossible to fully assess. Cognizant of the admonition
that “a court should not dismiss a complaint filed by a pro se litigant without granting
leave to amend at least once ‘when a liberal reading of the complaint gives any indication
that a valid claim might be stated,’” Bruce v. Tompkins Cnty. Dep’t of Soc. Servs. ex rel.
Kephart, 2015 WL 151029, at *4 (N.D.N.Y. Jan. 7, 2015) (quoting Branum v. Clark, 927
F.2d 698, 704-05 (2d Cir. 1991)), the Court recommends that the Complaint here be
dismissed with leave to replead. This will afford Plaintiff the opportunity to specifically
set forth the factual basis for his claims (rather than having the Court presume them) and
connect those factual allegations to his legal claims.
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Should Plaintiff be directed by the District Judge to file an amended complaint, I
offer the following guidance. Any such amended complaint, which shall supersede and
replace in its entirety the previous Complaint filed by Plaintiff, must clearly state the
nature of the suit and the basis for this Court’s jurisdiction. The body of Plaintiff’s
amended complaint must contain sequentially numbered paragraphs, as he did here,
containing only one act of misconduct per paragraph and should state with specificity the
legal claim for relief and the basis for damages. 	The pleading should be short and
specifically identify each cause of action, the specific facts given rise to each claim, and
the defendants associated with each. Plaintiff is referred to F ED . R. CIV . P. 8 and 10 as to
the proper form for his pleadings.
CONCLUSION
For the reasons stated herein, it is hereby
RECOMMENDED, that Plaintiff’s Complaint be DISMISSED with leave to
amend as set forth above pursuant to 28 U.S.C. §§ 1915(e) & 1915(A); and it is
ORDERED, that the request for additional time (Dkt. No. 7) is DENIED as moot;
and it is further
ORDERED, 	that 	the 	Clerk 	of 	the 	Court 	serve 	a 	copy 	of 	this 	Report-
Recommendation and Order upon the parties to this action.
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Pursuant to 28 U.S.C. § 636(b)(1), the parties have fourteen (14)2 days within
which to file written objections to the foregoing report. 	Such objections shall be filed
with the Clerk of the Court. FAILURE TO OBJECT TO THIS REPORT WITHIN
FOURTEEN (14) DAYS WILL PRECLUDE APPELLATE REVIEW. 	Roldan v.
Racette, 984 F.2d 85, 89 (2d Cir. 1993) (citing Small v. Sec’y of Health and Human Servs.,
892 F.2d 15 (2d Cir. 1989)); see also 28 U.S.C. § 636(b)(1); F ED . R. CIV . P. 72 & 6(a).
Dated: 	February 23, 2026
Albany, New York
2 If you are proceeding pro se and are served with this Order by mail, three additional days will be added to the
fourteen-day period, meaning that you have seventeen days from the date the order was mailed to you to serve and
file objections. F ED. R. CIV. P. 6(d). If the last day of that prescribed period falls on a Saturday, Sunday, or legal
holiday, then the deadline is extended until the end of the next day that is not a Saturday, Sunday, or legal holiday.
FED. R. C IV. P. 6(a)(1)(C).
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