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He swore at a police officer. Now he is embroiled in a battle for freedom of speech.

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Tony Rupp didn’t set out to become a fighter for the First Amendment. He was actually just looking for pasta.

In December 2016, Mr. Rupp, a Buffalo-area attorney, left Chef’s restauranta popular Italian spot in the center of the city, when he said he saw a black SUV – lights off – approaching two women crossing the street.

The driver came to a stop just in front of the women and, after disaster had been averted, continued driving as Mr. Rupp shouted, “Turn your lights on, you son of a bitch!”

The lawyer did not know that the driver was a Buffalo police officer, Todd C. McAlister, who pulled into the parking lot, followed Mr. Rupp and told him he was being detained. After about a half hour of arguing with the police in the parking lot, Mr. Rupp was stunned when the police handed him a ticket for violating the city’s noise ordinance, despite the argument taking place in a non -residential street near a busy highway. .

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

That interaction on a cold evening in Buffalo more than seven years ago set off a winding legal battle that has reached the upper echelons of the federal courts. At the end of January the United States Court of Appeals for the Second Circuit ruled that Mr. Rupp, 56, could pursue a lawsuit against the city and its police commissioner for malicious prosecution, First Amendment retaliation and wrongful arrest. The lawsuit 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 a major decision on how citizens can criticize government officials at a time of widespread reevaluation of the length and limits of freedom of expression. That debate has raged everywhere, from online forums and college campuses to protests racial bias in law enforcement and the war between Israel and Hamas. Book bans And other forms of government censorship have alarmed some First Amendment experts.

Last week, the Supreme Court heard arguments on a pair of laws — in Florida and Texas — that limit the ability of social media companies like Facebook to ban certain content from their platforms.

“In the In the recent climate, there has been an erosion of the principles and values ​​of the First Amendment speech,” said Norman Siegel, former executive director of the New York Civil Liberties Union. He said the Buffalo case could serve a “valuable purpose” in educating “judges and lower courts about the meaning and significance of freedom of speech.”

In Mr. Rupp’s case, a district court ruling — which the appeals court overturned in late January — had ruled that he did not deserve First Amendment protection, in part because he did not know he was addressing a police officer.

Such reasoning baffles Adam Steinbaugh, an attorney at the Foundation for Individual Rights and Expression, who said the Rupp case shows “we’re constantly fighting the same old battle.”

“The Supreme Court said long ago that what sets us apart from totalitarian states is the ability to criticize police officers, often in colorful language, without fear of being cuffed,” he said, adding: From officials should be expected, above any other employee of the state, not to use state violence in response to verbal criticism. We expect them to have thicker skin.”

Mr. Rupp says he would never have filed his charges if there had not been a much 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. Officers tackled the man, Wardel Davis III, when he tried to flee and resisted arrest. Officer Parisi admitted that he “struck Mr. Davis in the face several times,” an investigation by the Attorney General of New York.

Mr Davis – who had asthma – was handcuffed and placed on his stomach for several minutes. He stopped breathing and died shortly afterwards. Are dead led to protests in BuffaloAlthough the Attorney General cleared officers in December 2017, saying Mr. Davis died because of his medical condition, not his injuries.

Mr. Rupp said that if the police had responded to his complaints about the three officers at Chef’s — outlined in a lengthy letter to the commissioner soon afterward — Mr. Davis might not have died.

“No one listened to my letter, no one trained them and now a man is dead,” Mr Rupp said. “If they had just taught them how to turn the other cheek and not retaliate, like they did to me, with the summons, I thought this man might still be alive. So it worried me.”

Mr. Rupp’s noise fine was dismissed in the fall of 2017, but he filed a lawsuit anyway, arguing that the police had acted “intentionally, maliciously and with deliberate indifference” in treating him and issuing the noise ticket. However, four years later, a judge in Buffalo ruled against him, essentially saying he had been loud and rude.

“Given both the volume and nature of Rupp’s scream in the presence of bystanders, a reasonable person with normal sensitivities could become irritated and have their peace, comfort and tranquility disturbed,” wrote Judge William M. Skretny, of the Western District of New Yorkfollowing Buffalo criminal code.

The judge also wrote that because Mr. Rupp “did not know he was yelling at a police officer,” his speech was not “protected by the First Amendment in the form of criticism of law enforcement.”

Mr. Steinbaugh, the lawyer for the Foundation for Individual Rights and Expression, said that Mr. Rupp’s speech seemed clearly protected, even though he was uses a profanity and didn’t know that was him at first yelling at a police officer.

“It doesn’t matter at all if it’s a police officer,” he said, citing precedent dates back decades. “You have the right to use four-letter words.”

David Pozen, a law professor at Columbia Law School, said criticism of government officials is a fundamental constitutional right. “It would be strange to think that a slightly salty version of critical speech would lose First Amendment protection on that basis,” he said.

Sen. Patrick Gallivan, a former captain in the New York State Police and Erie County sheriff, said that while he could see the rationale behind both the district and circuit court decisions, the lawsuit also showed the challenges in navigating through controversial situations amidst changing social norms.

“There is a higher level of scrutiny,” said Gallivan, a Republican, adding: “This case simply illustrates how difficult it can be for a police officer to do their job.”

Mr. Siegel, the former executive director of the NYCLU, said Mr. Rupp’s initial resistance may have led to the ticket.

“My experience, after 54 years of doing this kind of thing, is that the police don’t like it when you talk back that way,” he said. “No one does. But especially the police.”

Faiza Patel, the senior director of the Liberty and National Security Program at the Brennan Center for Justice, said Mr. Rupp’s case comes during “a period of tumult for free speech.”

“We are in a period of reevaluation,” Ms Patel said, citing thorny issues such as hate speech, social media misinformation and online threats.

The city, the police department and an attorney for the three police officers did not return requests for comment on the lawsuit. Agent McAlister, who has been active in a group in Buffalo which aims to bridge relations between the community and the police, recently promoted.

The case also redefined the trajectory of Mr. Rupp changed. After working primarily as an attorney for many years, he expanded his firm’s practice into the realm of civil rights, handling dozens of cases across a small group of newly hired attorneys.

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 looking for this fight, he’s hopeful he wins and contributes to others’ understanding of the right to free speech.

“The most interesting famous case I will ever be involved in is my own case,” he said, adding: “I have contributed to the body of constitutional law. And I have a good feeling about that.”

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