He Cursed at a Police Officer. Now He’s Caught in a Free Speech Fight.

Tony Rupp didn’t intend to become a fighter for the First Amendment. He was really just out for some pasta.

In December 2016, Mr. Rupp, a Buffalo-area lawyer, was leaving Chef’s Restaurant, a popular Italian place in the city’s downtown, when he said he saw a black SUV — its lights off — bearing down on two women crossing the street.

The driver came to a halt just short of the women, and then, disaster averted, kept going as Mr. Rupp shouted, “Turn your lights on, asshole!”

Little did the lawyer know that the driver was a Buffalo police officer, Todd C. McAlister, who turned into the parking lot, followed Mr. Rupp and told him that he was being detained. After about a half-hour, which Mr. Rupp spent arguing with the police in the parking lot, he was stunned when the police handed him a ticket for violating the city’s noise ordinance, despite the argument occurring on a nonresidential street near a buzzing freeway.

“Nobody was offended by my noise,” he said, adding: “This was about the content of my speech.”

That interaction on a cold Buffalo night more than seven years ago has set off a winding legal battle that has reached the upper echelons of federal courts. In late January, the United States Court of Appeals for the Second Circuit ruled that Mr. Rupp, 56, could continue a suit against the city and its police commissioner for malicious prosecution, First Amendment retaliation and wrongful arrest. The suit also names three officers involved in the incident at Chef’s: Mr. McAlister, Nicholas Parisi and a lieutenant, Jeffrey Giallella.

The case could result in an important decision regarding how citizens can criticize public officials at a time of widespread re-evaluation of the lengths and limits of free speech. That debate has raged everywhere from online forums and college campuses to protests over racial bias in law enforcement and the Israel-Hamas war. Book bans and other acts of government censorship have troubled some First Amendment experts.

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