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.
Just last week, the Supreme Court heard arguments about a pair of laws — in Florida and Texas — limiting the ability of social media companies like Facebook to ban certain content from their platforms.
“In the recent climate, there’s been an erosion of the principles and values of First Amendment speech,” said Norman Siegel, a former executive director of the New York Civil Liberties Union. He said the Buffalo case could serve a “valuable purpose” in educating “judges and the lower courts as to the meaning and significance of free speech.”
In Mr. Rupp’s case, a district-court ruling — which the appeals court overturned in late January — had held that he did not deserve First Amendment protection, in part because he did not know he was addressing a police officer.
Such reasoning boggles Adam Steinbaugh, a lawyer with the Foundation for Individual Rights and Expression, who said that the Rupp case shows “that we’re constantly fighting the same old battles.”
“The Supreme Court said long ago that what distinguishes us from totalitarian states is the ability to criticize police officers, often in colorful language, without having to fear that you’re going to wind up in cuffs,” he said, adding, “Police officers, above any other employee of the state, should be trusted or expected not to use the force of the state in response to verbal criticism. We expect them to have thicker skins.”
Mr. Rupp says he never would have filed his suit had it not been for a far more serious incident involving the same officer about two months later, in February 2017.
Officer McAlister and his partner, Officer Parisi, confronted a 20-year-old man on suspicion of a drug offense. The officers tackled the man, Wardel Davis III, when he tried to flee and resisted arrest. Officer Parisi admitted to “punching Mr. Davis several times in the face,” according to an investigation by the New York attorney general.
Mr. Davis — who had asthma — was handcuffed and placed on his stomach for several minutes. He stopped breathing and died shortly after. His death set off protests in Buffalo, though the attorney general cleared the officers in December 2017, saying Mr. Davis died because of his medical condition, not his injuries.
Mr. Rupp said that if the Police Department had responded to his complaints about the three officers at Chef’s — outlined in a lengthy letter to the commissioner soon after — Mr. Davis might not have died.
“Nobody heeded my letter, nobody gave them training and now a guy is dead,” Mr. Rupp said. “If they had just trained them on how to turn the other cheek and not be retaliatory, which they were with me, with the summons, I thought this guy might still be alive. So it troubled me.”
Mr. Rupp’s noise ticket was dismissed in fall 2017, but he sued anyway, arguing that the police had acted “intentionally, maliciously and with a deliberate indifference” in their treatment of him and issuing the noise citation. Four years later, however, a district court judge in Buffalo ruled against him, essentially saying that he had been loud and crude.
“Given both the volume and nature of Rupp’s yell in the presence of bystanders, a reasonable person of normal sensitivities could be annoyed and have their quiet, comfort and repose disturbed,” wrote Judge William M. Skretny, of the Western District of New York, echoing Buffalo’s criminal code.
The judge also wrote that because Mr. Rupp “did not know that he was yelling at a police officer,” his speech was not “protected by the First Amendment in the form of law enforcement criticism.”
Mr. Steinbaugh, the lawyer with the Foundation for Individual Rights and Expression, said Mr. Rupp’s speech seemed clearly protected, even though he used a profanity and didn’t know at first that he was yelling at a police officer.
“It doesn’t matter if it’s a police officer at all,” he said, citing precedent dating back decades. “You have the right to use four-letter words.”
David Pozen, a professor of law at Columbia Law School, said criticism of public officials is a core constitutional right. “It would be odd to think that a slightly salty version of critical speech loses First Amendment protection on that basis,” he said.
State Senator Patrick Gallivan, a former captain with the New York State Police and Erie County sheriff, said while he could see the rationale for both the district and circuit court decisions, the lawsuit also showed the challenges in navigating contentious situations amid changing societal norms.
“There’s a higher level of scrutiny,” said Mr. Gallivan, a Republican, adding, “This case simply illustrates how difficult it can be for a police officer to do their jobs.”
Mr. Siegel, the former executive director of the N.Y.C.L.U., said that Mr. Rupp’s initial defiance may have led to the ticket.
“My experience, after 54 years of doing this stuff, is that the cops don’t like when you talk back that way,” he said. “Nobody does. But especially cops.”
Faiza Patel, the senior director of the Brennan Center for Justice’s Liberty and National Security Program, says that Mr. Rupp’s case is happening during “a period of tumult for free speech.”
“We’re in a period of re-evaluation,” said Ms. Patel, mentioning thorny issues like hate speech, social-media disinformation and online threats.
The city, police force and a lawyer for the three police officers did not return requests for comment on the suit. Officer McAlister, who has been active in a group in Buffalo that aims to bridge relations between the community and the police, was recently promoted.
The case has also altered the trajectory of Mr. Rupp’s career. After years of primarily working as a defense lawyer, he has expanded his firm’s practice into the realm of civil rights, taking up dozens of cases, parceled among a small coterie of newly hired lawyers.
Mr. Rupp is seeking only $1 in damages and legal fees, though he hopes “to send a message” to the city. And while he says he wasn’t seeking this fight, he is hopeful that he wins, and adds to others’ understanding of free speech rights.
“The most interesting famous case that I’m ever going to be involved in is my own case,” he said, adding: “I contributed to the body of constitutional law. And I feel pretty good about that.”