Massimino v. Benoit

Court of Appeals for the Second Circuit·Decided August 17, 2026·No. 25-1104·Published

Opinion

25-1104 Massimino v. Benoit

In the

United States Court of Appeals for the Second Circuit

August Term 2025

Argued: March 2, 2026

Decided: August 17, 2026

No. 25-1104

KEITH MASSIMINO,

Plaintiff-Appellant,

v.

MATTHEW BENOIT, FRANK LAONE, Defendants-Appellees.

Appeal from the United States District Court for the District of Connecticut No. 21-cv-1132, Robert N. Chatigny, District Judge.

Before: RAGGI, PÉREZ, and MERRIAM, Circuit Judges.

Keith Massimino alleges that two police officers—Matthew Benoit and Frank Laone—violated his rights under the First and Fourth Amendments to the United States Constitution when they detained and arrested him while he recorded the exterior of the Waterbury Police Department building from a public sidewalk. He argues that the First Amendment protects his right to record law

25-1104 Massimino v. Benoit

enforcement activity in public, and that this right encompasses recording a police department building from a public sidewalk. Thus, he contends, Benoit and Laone lacked any reasonable basis to detain, arrest, and prosecute him. On competing summary judgment motions, the District Court ruled in favor of the officers on all of Massimino’s claims. We affirm.

We begin by joining a growing chorus of our sister circuits that have recognized a First Amendment right to record law enforcement activity in public. That right encompasses Massimino’s recording of the exterior of a police station from a public sidewalk. However, because that right was not clearly established at the time in question, Benoit and Laone are entitled to qualified immunity as to Massimino’s First Amendment claim.

Next, although Massimino engaged in First Amendment-protected activity, we nevertheless conclude that Benoit and Laone had reasonable suspicion to briefly detain and question him. Massimino’s subsequent failure to comply with the officers’ order that he produce identification afforded the officers probable cause to believe Massimino had violated Conn. Gen. Stat. § 53a-167a. These related conclusions defeat Massimino’s Fourth Amendment claims concerning his detention and arrest. Because the officers had probable cause to arrest Massimino, and there was probable cause to continue at each stage of the prosecution, Massimino cannot maintain a malicious prosecution claim either.

Judge Raggi concurs in a separate opinion.

DAN BARRETT (Elana Bildner, Jaclyn Blickley, on the brief), American Civil Liberties Union Foundation of Connecticut, Hartford, CT, for Plaintiff-Appellant.

JOSEPH A. MENGACCI (Daniel J. Foster, on the brief), Office of the Corporation Counsel, Waterbury, CT, for Defendants-Appellees.

25-1104 Massimino v. Benoit

MYRNA PÉREZ, Circuit Judge:

Keith Massimino alleges that two police officers—Matthew Benoit and Frank Laone—violated his rights under the First and Fourth Amendments to the United States Constitution when they detained and arrested him while he recorded the exterior of the Waterbury Police Department building from a public sidewalk. He argues that the First Amendment protects his right to record law enforcement activity in public, and that this right encompasses recording a police department building from a public sidewalk. Thus, he contends, Benoit and Laone lacked any reasonable basis to detain, arrest, and prosecute him. On competing summary judgment motions, the District Court ruled in favor of the officers on all of Massimino’s claims. We affirm.

We begin by joining a growing chorus of our sister circuits that have recognized a First Amendment right to record law enforcement activity in public. That right encompasses Massimino’s recording of the exterior 1 of a police station from a public sidewalk. However, because that right was not clearly established

1 Exterior, as it is used throughout this opinion, means the areas visible from a publicly accessible area outside the police station.

25-1104 Massimino v. Benoit

at the time in question, Benoit and Laone are entitled to qualified immunity as to Massimino’s First Amendment claim.

Next, although Massimino engaged in First Amendment-protected activity, we nevertheless conclude that Benoit and Laone had reasonable suspicion to briefly detain and question him. Massimino’s subsequent failure to comply with the officers’ order that he produce identification afforded the officers probable cause to believe Massimino had violated Conn. Gen. Stat. § 53a-167a. These related conclusions defeat Massimino’s Fourth Amendment claims concerning his detention and arrest. Because the officers had probable cause to arrest Massimino, and there was probable cause to continue at each stage of the prosecution, Massimino cannot maintain a malicious prosecution claim either.

BACKGROUND

I. Massimino’s Detention and Arrest Keith Massimino is a self-described “First Amendment auditing hobbyist.”

Appellant’s Br. at 3. On the evening of October 30, 2018, he conducted a so-called “First Amendment audit” outside the Waterbury Police Department in Waterbury, Connecticut. The “audit” consisted of Massimino walking around the

25-1104 Massimino v. Benoit

exterior of the police station recording a video of the station and its surrounding areas. These areas included the closed door of the entrance to the “Youth Division” and the first level of an open-air parking garage attached to the police station containing police vehicles. At all times, Massimino remained on a public sidewalk.

After Massimino had been recording for roughly six and a half minutes, Officers Matthew Benoit and Frank Laone approached and questioned him. Massimino said that he was “a journalist getting content for a story” but declined to answer the officers’ follow-up questions. Benoit and Laone told Massimino he was not allowed to videotape the police station and requested he produce identification. They expressed concern that Massimino could be planning some kind of attack on the building. When Massimino refused to provide identification, the officers asserted that their request was “a lawful order.” Massimino again refused to produce identification, and the officers arrested him.

Massimino was charged with violating Conn. Gen. Stat. § 53a-167a, which prohibits certain acts of interference with police activity, such as “obstruct[ing], resist[ing], hinder[ing] or endanger[ing] any peace officer . . . in the performance

25-1104 Massimino v. Benoit

of such peace officer’s . . . duties.” He was held for several hours and then released. The lone charge against Massimino was ultimately dismissed roughly two and a half years later. See State v. Massimino, No. U04W-CR18-0454740-S (Conn. Super. Ct. May 21, 2021).

II. Procedural History Massimino brings three claims against Benoit and Laone pursuant to 42 U.S.C. § 1983: (1) a First Amendment claim for violating his right to record the police station; (2) a Fourth Amendment claim for detaining and subsequently arresting him; and (3) a malicious prosecution claim. The officers assert they are entitled to qualified immunity as to all of Massimino’s claims. The parties cross- moved for summary judgment, and the District Court granted the officers’ motion.

The District Court concluded that the officers were entitled to qualified immunity as to Massimino’s First Amendment claim, and to summary judgment on the merits of the Fourth Amendment claims. See Massimino v. Benoit, No. 3:21- cv-1132, 2025 WL 975177, at *2–5 (D. Conn. Mar. 31, 2025). On the First Amendment claim, the District Court concluded that Massimino lacked a clearly established right to record the police station. Id. at *2–3. On the Fourth

25-1104 Massimino v. Benoit

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