Natalia Danielle Middleton v. Police Officer Claire Infante

Opinion

UNITED STATES DISTRICT COURT SOUTHERN DISTRICT OF NEW YORK NATALIA DANIELLE MIDDLETON, Plaintiff, _ against - OPINION & ORDER 24-cv-8217 (ER) POLICE OFFICER CLAIRE INFANTE, Defendant.

RAMOS, D.J.: Natalia Danielle Middleton, proceeding pro se, filed a complaint on October 28, 2024, pursuant to 42 U.S.C. § 1983, asserting claims for excessive force and false arrest against police officer Claire Infante of the New York Police Department (“NYPD”). Doc. 1. Before the Court is Infante’s motion for judgment on the pleadings and Ms. Mid- dleton’s motion for leave to file to file an amended complaint. Docs. 22, 48. For the rea- sons stated below, Infante’s motion for judgment on the pleadings is DENIED without prejudice and Ms. Middleton’s motion for leave to file an amended complaint is GRANTED.

I. BACKGROUND

A. Factual Background Tn early 2024, Ms. Middleton was living in an apartment in the Bronx. Doc. 1 at 3. On May 1, 2024, she decided that she no longer wanted to live in the apartment, and between 10:00 p.m. and 11:00 p.m., she attempted to leave with her one-year-old son. Id. Ms. Middleton’s mother and brother tried to stop her, and they eventually called 911 for police assistance. /d. Two officers from the NYPD’s 41st Precinct arrived, and Ms. Middleton and her mother each gave a statement to a male officer. /d. at 1-2. Neither

police officer informed Ms. Middleton that she was not free to leave. Jd. Ms. Middleton then began walking away with her child, intending to return to the apartment. /d. At that point, a group of police officers, including Officer Infante, rushed toward her and her child. Jd. Officer Infante put Plaintiff in a ““chokehold” and handcuffed her. /d. Ms. Middleton states she was not read her rights nor informed of the grounds of her detention. Id. Ms. Middleton states that she suffers from PTSD due to the excessive force used by Officer Infante. /d. She further alleges that she was taken in handcuffs to the emergency room at Lincoln Medical Center, and was eventually involuntarily admitted to a psychiat- ric facility, where she remained until May 14, 2024. Id.

B. Procedural Background Ms. Middleton filed her pro se complaint on October 28, 2024. Doc. 1. She brings this action pursuant to 42 U.S.C. § 1983, asserting claims for excessive force and false arrest against Infante of the NYPD’s 41st precinct. Jd. She seeks compensatory damages for her emotional and physical harm, punitive damages for Infante’s alleged un- lawful actions, and injunctive relief “to prevent further violation[s] of civil rights by 41st precinct officers.” /d. at 4. On June 11, 2025, Infante filed a motion for judgment on the pleadings. Doc. 22. On August 19, 2025, Ms. Middleton filed six documents, one of which was styled as “Verified Declaration and Lawful Challenge to Respondent’s Motion to Dismiss.” Doc. 38.! On September 16, 2025, Infante filed her reply brief in support of her motion for judgment on the pleadings. Doc. 43.

' Tn addition to the “Verified Declaration and Lawful Challenge to Respondent’s Motion to Dismiss,” on August 19, 2025, Ms. Middleton filed a “Judicial Mandate for Preservation of Claims, Evidence and

On February 10, 2026, Ms. Middleton filed a motion for leave to file an amended complaint, which Infante opposed on February 24, 2026. Docs. 48, 52. On February 27, 2026, Ms. Middleton filed a “Supplemental Memorandum of Law in Support” of her mo- tion for leave to file an amended complaint. Doc. 55. Also on February 27, 2026, Ms. Middleton filed a motion for leave to file an op- position to officer Infante’s June 11, 2025 motion for judgment on the pleadings, arguing that she did not realize the motion was “fully briefed” and that her earlier submissions, while responsive to defendant’s motion, did not constitute a comprehensive opposition addressing all legal and factual issues raised by defendant. Doc. 54 at 1-3. Ms. Middle- ton attached her proposed opposition brief. Jd. at 18-44. On March 5, 2026, Ms. Middleton filed a reply in support of her motion for leave to amend the complaint. Doc. 57.

Il. DISCUSSION The Court will first address the motion to amend. See GGC International Limited v. Ver, No. 24 Civ. 1533 (JPC), 2025 WL 81319, at *1 (S.D.N.Y. Jan. 13, 2025) (“When a court is faced with [a] motion[ ] to dismiss one complaint and a motion for leave to file an amended complaint, the court may focus first on the motion for leave to amend be- cause granting the motion for leave to amend moots the pending motion[ ] to dismiss.”’) (quoting Cummins, Inc. v. New York Life Insurance, No. 10 Civ. 9252 (TPG), 2012 WL 3870308, at *2 (S.D.N.Y. Sept. 6, 2012))).

Equitable Adjudication”; a “Notice of Obligation to Acknowledge and Record Delivered Instruments”; a “Constitutional Notice of Claim’; a “Notice of Claim and Declaration of Status”; and an “Affidavit of Beneficiary Standing in the State Claim.” Docs. 34-39.

A. Motion for Leave to Amend the Complaint Legal Standard

Rule 15 of the Federal Rules of Civil Procedure allows a party to amend its com- plaint pursuant to the other party’s written consent or the court’s leave. Fed. R. Civ. P. 15. Rule 15(a) states that “[t]he court should freely give leave [to amend] when justice so requires.” Fed. R. Civ. P. 15(a)(2). Under Rule 15(a), “a motion to amend should be de- nied only if the moving party has unduly delayed or acted in bad faith, the opposing party will be unfairly prejudiced if leave is granted, or the proposed amendment is futile.” See Agerbrink v. Model Service LLC, 155 F. Supp. 3d 448, 452 (S.D.N.Y. 2016). As a gen- eral rule, leave to amend a complaint should be freely granted. Jin v. Metropolitan Life Insurance Co., 310 F.3d 84, 101 (2d Cir. 2002). District courts have broad discretion in deciding whether to grant leave to amend. Pasternack v. Laboratory Corp. of America,

892 F. Supp. 2d 540, 549 (S.D.N.Y. 2012) (citation omitted). The Court notes that Ms. Middleton is proceeding pro se. “A pro se litigant’s pa- pers must be construed liberally ‘to raise the strongest arguments they suggest.’” Jules v. Andre Balazs Properties, No. 20-cv-10500 (LGS), 2023 WL 5935626, at *2 (S.D.N.Y. Sept. 12, 2023) (quoting Publicola v. Lomenzo, 54 F.4th 108, 111 (2d Cir. 2022)). The obligation to be lenient while reading a pro se plaintiff's pleadings “applies with particu- lar force when the plaintiff's civil rights are at issue.” Jackson v. N.Y.S. Department of Labor, 709 F. Supp. 2d 218, 224 (S.D.N.Y. 2010) (citing McEachin v. McGuinnis, 357 F.3d 197, 200 (2d Cir. 2004)). At the same time, pro se status “does not exempt a party from compliance with relevant rules of procedural and substantive law.” Triestman v.

Federal Bureau of Prisons, 470 F.3d 471, 477 (2d Cir. 2006). 2. Analysis In her initial motion for leave to amend the complaint, Ms. Middleton states that the motion is made for “the limited purpose of correcting misidentified parties and cor- recting the lawful identity of the [Plaintiff], without altering the underlying facts or sub- stantive claims asserted.” Doc. 48 at 1. With respect to the misidentified party, Ms. Mid- dleton writes that she “was unaware that, as a matter of law, the proper municipal [defendant] is the City of New York, rather than individual municipal employees or agen- cies” and as such, she wants to substitute the City of New York as the defendant. /d. at 2.2 With respect to her lawful identity, Ms. Middleton argues that the original complaint is brought in the name of “Natalia Middleton,” and not her full and lawful legal name “Natalia Danielle Middleton.” /d. at 2. Officer Infante opposes Ms. Middleton’s request, arguing mainly that such an amendment would be futile. Doc. 52 at 1. With respect to the request to substitute the City of New York as defendant, Infante argues that: (1) “even liberally construed, [Ms. Middleton]’s [c]omplaint contains no allegations plausibly suggesting that a municipal policy or custom caused the purported constitutional violations. . . . [Ms. Middleton] does not identify any specific policy or custom or suggest the existence of ‘widespread munic- ipal practice,’” and (2) the proposed amendment would not “salvage or support any state

2 Ms. Middleton also writes that she “has . . . learned that claims arising from the acts of NYPD officers must be brought against the City of New York, as NYPD is not a suable entity.” Doc. 48 at 2. Ms. Middleton is correct, insofar as the police department is not a suable entity. See Jenkins v. City of New York, 478 F.3d 76, n.19 (2d Cir. 2007) (“The district court correctly noted that the NYPD is a non-suable agency”). However, lawsuits based on the actions of a police officer may be brought both against the City of New York and the officer in his individual capacity, though that officer may be protected by qualified immunity. See e.g. Garnes y. City of New York, No. 22-CV-01769 (ER), 2025 WL 605466, at *1 (S.D.N-Y. Feb. 25, 2025) (plaintiff bringing claims against the City of New York and the individual police officers who arrested him).

law claim against the City.” Id. at 3. With respect to updating Middleton’s name, Infante argues that, because “Plaintiff’s [initial] [c]omplaint already identifies her as ‘Natalia Danielle Middleton’ in the caption,” the request is unnecessary. Id. After Infante’s opposition was filed, Ms. Middleton filed two additional docu- ments to support her motion: a “Supplemental Memorandum of Law in Support” of the

motion, Doc. 55, and a reply brief, Doc. 57. In those documents, Ms. Middleton includes a host of new allegations, including that: in the 911 call, her mother falsely alleged that a person she identified as “Natalia Middleton” had a history of Borderline Personality Dis- order and posed a danger to herself and others; at no point did the responding officers re- quest or examine any form of identification from Ms. Middleton, nor did they ask for her name; the officers did not attempt to verify whether she was the same person described in her mother’s 911 call; the officers tackled her to the ground; and in documenting the inci- dent, the NYPD created a report identifying her as “Natalia Middleton” with a birthdate that was incorrect. Doc. 55 at 3–8; see Doc. 57 at 7–11. Ms. Middleton further asserts

that this incident “was not an isolated mistake . . . but reflects a pattern, practice and pol- icy of the City of New York” and that there is a “systematic failure to verify identity be- fore [police officers] execut[e] seizures, particularly in cases involving psychiatric allega- tions. . .” Doc. 55 at 11; Doc. 57 at 7–11. She argues that the City of New York has a policy or custom of failing to verify the identity of a person prior to seizure; that the city has a policy or custom of relying on unverified third-party allegations; that the city has failed to train officers on fourth amendment requirements; that the policy permits invol- untary psychiatric detention and warrantless entry into private dwellings without due pro- cess; that the city failed to train officers on parental rights; and that the city is deliberately indifferent to these constitutional risks. Doc. 55 at 20-27; Doc. 57 at 7-11.° She further re-alleges her assertion that it is necessary to correct her name from “Natalia Middleton” to “Natalia Danielle Middleton” to clearly and unambiguously identify the real party in interest. Doc. 57 at 14. The Second Circuit has held that leave to amend may be denied on the basis of fu- tility when it is “beyond doubt that the plaintiff can prove no set of facts in support of his amended claims.” Pangburn v. Culberston, 200 F.3d 65, 71 (2d Cir. 1999) (citation and internal quotation marks omitted). In determining whether an amendment ts futile, the court evaluates the amended complaint “through the prism of a Rule 12(b)(6) analysis.” Henneberry v. Sumitomo Corp. of America, 415 F. Supp. 2d 423, 433 (S.D.N-Y. 2006). Following this standard, courts accept a plaintiffs factual allegations as true and draw reasonable inferences in their favor. /d.; see also Erickson v. Pardus, 551 U.S. 89, 94 (2007). The trial court “has broad discretion in determining whether to grant leave to amend.” Gurary v. Winehouse, 235 F.3d 792, 801 (2d Cir. 2000). With respect to updating Ms. Middleton’s name to “Natalia Danielle Middleton,” the Court agrees with officer Infante, that such a request is not sufficient grounds to grant a motion to amend the complaint. See Doc. 52 at 3. Ms. Middleton’s initial complaint already lists her full name as “Natalia Danielle Middleton” in the caption. Doc. 1 at 1. To the extent that Ms. Middleton wants her name to be updated in the docket, the Clerk of Court is respectfully directed to change plaintiffs name from “Natalia Middleton” to “Natalia Danielle Middleton.”

>In her reply brief, Ms. Middleton also clarifies that she asserts “claims under 42 U.S.C. § 1983 for violations of the Fourth and Fourteenth Amendments to the United States” and that she “does not assert any state law claims.” Doc. 57 at 12.

With respect to Ms. Middleton’s arguments concerning the liability of the City of New York, as a preliminary matter, while it is generally improper to consider new argu- ments in a reply brief; due to the liberal standard concerning motions for leave to amend a complaint, Ms. Middleton’s pro se status, and concerns as to judicial economy," the Court considers the new allegations raised in her supplemental memorandum and her re- ply brief. Monell liability is a particular theory of liability for § 1983 claims against munici- palities. See Monell v. Department of Social Services of the City of New York, 436 U.S. 658, 694 (1978) (“[I]t is when execution of a government’s policy or custom .. . inflicts the injury that the government as an entity is responsible under § 1983”); see also Con- nick v. Thompson, 563 U.S. 51, 60 (2011) (“A municipality or other local government may be liable under this section [1983] if the governmental body itself ‘subjects’ a person to a deprivation of rights or ‘causes’ a person ‘to be subjected’ to such deprivation.”) (quoting Monell, 436 US. at 692). “[T]o hold a city liable under § 1983 for the unconsti- tutional actions of its employees, a plaintiff is required to plead and prove three elements: (1) an official policy or custom that (2) causes the plaintiff to be subjected to (3) a denial of a constitutional right.” Wray v. City of New York, 490 F.3d 189, 195 (2d Cir. 2007) (quotation marks and citation omitted). Infante correctly identifies that the initial complaint did not make any allegation that Infante’s conduct was pursuant to a policy, custom, or widespread municipal

+ The Court notes that, if it were to deny Ms. Middleton leave to amend her complaint on the grounds that her reply brief includes additional proposed facts that were not mentioned in her initial brief; Ms. Middleton would be free subsequently to file another motion for leave to amend her complaint with those city-wide policy allegations.

practice. See Doc. 52 at 3 (“Indeed, [Ms. Middleton] does not identify any specific pol- icy or custom or suggest the existence of a ‘widespread’ municipal practice . . .”); Doc. 1. Therefore, merely adding the City of New York as a defendant without updating any of the factual allegations would be legally insufficient to demonstrate Monell liability, and therefore futile. See e.g. Megginson v. City of New York, No. 23 Civ. 6798 (ER), 2025

WL 902644, at *9 (S.D.N.Y. Mar. 25, 2025) (“[Plaintiff] nowhere claims that any of the alleged constitutional violations took place as a result of a City policy, practice or cus- tom, a failure to train or supervise its employees. . . . Therefore, [Plaintiff] has not ade- quately pleaded a Monell claim against the City, and his claims against it are dismissed.”) (internal citations omitted). However, it is clear from Ms. Middleton’s reply and her “supplemental memoran- dum” that she now intends to amend her complaint to include allegations that her experi- ence was a part of a city-wide policy, practice, custom, and a failure to train. See Docs. 55, 57. Deciding whether these allegations are sufficiently plausible to withstand a mo-

tion to dismiss or for judgment on the pleadings is premature, as Ms. Middleton’s amended complaint is yet to be filed and Infante’s arguments concerning futility are premised on an absence of allegations concerning a city policy, custom, or wide-spread practice. See Doc. 52; see also Ciotti v. City of New York, No. 23 CIV. 10279 (ER), 2025 WL 308022, at *21 (S.D.N.Y. Jan. 27, 2025) (“Mere allegations of a municipal custom, a practice of tolerating official misconduct, or inadequate training and/or supervision are insufficient to demonstrate the existence of such a custom unless supported by factual de- tails.”); Megginson v. City of New York, No. 23 Civ. 6798 (ER), 2025 WL 902644, at *8 (S.D.N.Y. Mar. 25, 2025) (“In the context of a motion to dismiss, ‘a plaintiff must make factual allegations that support a plausible inference that the constitutional violation took place pursuant either to a formal course of action officially promulgated by the munici- pality’s governing authority or the act of a person with policymaking authority for the municipality.’) (quoting Missel v. County of Monroe, 351 F. App’x 543, 545 (2d Cir. 2009) (summary order)).° Accordingly, Ms. Middleton’s motion for leave to amend her complaint is GRANTED.

B. Motion for Judgment on the Pleadings: Because the Court has granted Ms. Middleton leave to amend her complaint, it denies the motion for judgment on the pleadings as moot. See GGC International Lim- ited, 2025 WL 81319, at *1 (“[G]ranting the motion for leave to amend moots the pend- ing motions to dismiss.” (quoting Cummins, 2012 WL 3870308, at *2)). The motion is denied without prejudice. Infante is granted leave to renew the motion after Ms. Middle- ton files the amended complaint. Il. CONCLUSION For the reasons stated below, Infante’s motion for judgment on the pleadings is DENIED without prejudice and Ms. Middleton’s motion for leave to file an amended

> Infante also briefly argues that “requiring Defendant to re-brief the same legal arguments in response to unchanged allegations would needlessly duplicate prior motion practice, impose unnecessary prejudice, and delay the potential resolution of this action.” Doc. 52 at 3. The Court is sympathetic to those arguments; however, as a preliminary matter, the Second Circuit has asserted that “mere delay . .. absent a showing of bad faith or undue prejudice, does not provide a basis for a district court to deny the right to amend.” Altowaiti v. Cissna, 2020 WL 2036703, at *4 (S.D.N.Y. Apr. 28, 2020) (quoting State Teachers Retirement Board v. Fluor Corp., 654 F.2d 843, 856 (2d Cir. 1981)). Further, to the extent that Infante 1s concerned about additional motion practice, as the Court discusses below, Infante is granted leave to renew her motion for sudgment on the pleadings after Ms. Middleton files her amended complaint.

complaint is GRANTED. Ms. Middleton 1s directed to file her amended complaint by April 30, 2026. The Clerk of Court is respectfully directed to change plaintiff's name from “Nata- lia Middleton” to “Natalia Danielle Middleton,” on the docket. The Clerk of Court is also respectfully directed to terminate the motions, Docs. 22, 48, 54.

It is SO ORDERED.

Dated: March 25, 2026 20%" New York, New York FE \V ve EDGARDO Ramos, U.S.D.J.