WASHINGTON — About a decade ago, the leaders of a Florida city held a closed-door meeting to discuss how to intimidate and silence a critic named Fane Lozman. So far, their plan has not worked.
Mr. Lozman calls himself “a persistent and tenacious underdog,” which may be an understatement. He is an indefatigable gadfly and an unusually successful litigant.
In 2013, he won his first Supreme Court case against the city, Riviera Beach. By a 7-to-2 vote, the justices ruled that the city had misused maritime law to seize and destroy his houseboat. Chief Justice John G. Roberts Jr. called the decision his favorite of the term.
Last month, the Supreme Court agreed to hear another appeal from Mr. Lozman. Repeat appearances in the court by the same adversaries are unusual, and they tend to involve different stages in the same case. Mr. Lozman has pulled off the rare feat of hauling the city into the Supreme Court in two separate cases.
The new one has its roots in that closed-door session, which took place in June 2006. According to a transcript, which was later made public under Florida’s freedom-of-information law, the city’s leaders spoke freely about finding a way to investigate and threaten Mr. Lozman.
Elizabeth Wade, a city councilwoman, said “it would help to intimidate” Mr. Lozman and to make him feel “unwarranted heat.”
Five months later, Mr. Lozman rose to address the City Council during the part of a public session set aside for comments from residents. He had barely started talking when Ms. Wade called for a police officer.
“Carry him out,” she said.
Mr. Lozman refused to go. “I have a right to make my public comment,” he said.
Ms. Wade disagreed. “Take him out,” she said.
A video of the episode shows Mr. Lozman being handcuffed and led away.
He was charged with disorderly conduct and resisting arrest, but prosecutors dropped the charges, saying there was “no reasonable likelihood of successful prosecution.”
Mr. Lozman sued, saying he had been arrested in retaliation for exercising his First Amendment rights. The arrest was payback, he said, for his criticism of the city’s plan to redevelop the waterfront by taking private property using eminent domain.
The federal appeals court in Atlanta said Mr. Lozman had made a compelling point. “He seems to have established a sufficient causal nexus between Councilperson Wade and the alleged constitutional injury of his arrest,” the court said in an unsigned opinion in February.
Despite that, the court ruled that Mr. Lozman could not sue. Since there had been probable cause for the arrest, the court said, it did not matter that it might also have been motivated by retaliation.
Oddly, the court did not say there had been probable cause to arrest Mr. Lozman for the crimes he had been charged with. Instead, the court said the officer had had probable cause to believe that Mr. Lozman “was committing, or about to commit, the offense of disturbing a lawful assembly.”
In an interview, Mr. Lozman said he found this perplexing. “Can you arrest somebody and come up with some probable cause argument even if it’s eight years later?” he asked.
The question of whether the existence of probable cause is always enough to defeat a lawsuit claiming retaliatory arrest has divided the appeals courts. The Supreme Court agreed in 2011 to decide the question but ended up ducking it.
At the argument in that case, Reichle v. Howards, two members of the court sketched out the competing arguments.
Justice Sonia Sotomayor said that it was almost always possible to concoct probable cause for an arrest. “If you’re jaywalking, there’s probable cause,” Justice Sonia Sotomayor said.
But Chief Justice Roberts worried that people could game the system. For instance, he said, drivers could put “I Hate the Police” bumper stickers on their cars and then claim that any arrest was in retaliation for exercising their First Amendment rights.
“It’s not because I was going 60 miles an hour,” Chief Justice Roberts said, imaging what a driver might say. “It’s because of my bumper sticker.”
In urging the Supreme Court to hear the case, Pamela S. Karlan, a lawyer for Mr. Lozman, wrote that conflicts between the government and its critics were on the rise.
“Recent years have seen a fresh surge of civic engagement, much of it involving criticism of the government,” she wrote. “Thus, the risk of retaliatory arrests remains a pressing concern.”
A supporting brief from the First Amendment Foundation said the appeals court decision in Mr. Lozman’s case effectively made it impossible to sue for retaliatory arrest on First Amendment grounds. “Given the wide range of offenses that can lead to arrest in today’s world,” the brief said, “the decision below effectively immunizes municipalities and officials against First Amendment retaliatory arrest claims.”
In a brief urging the justices not to hear Mr. Lozman’s appeal, Shay Dvoretzky, a lawyer for Riviera Beach, said the decision to arrest Mr. Lozman had been made by the police officer, who did not know him and bore him no ill will. Mr. Dvoretzky cautioned the court against setting a precedent that “would create a federal case almost every time an officer arrests someone, as there is almost always some verbal interaction between officer and arrestee.”
For his part, Mr. Lozman said he was thrilled that the Supreme Court had agreed to hear from him a second time. He added that he hoped the justices would protect critics of the government.
“What makes America beautiful is our personal freedoms,” he said. “Constitutionally protected free speech cannot be suppressed at the whim of elected officials and public servants.”