The Supreme Court is considering whether someone who believes he was arrested in violation of his free speech rights can pursue a claim of retaliation against the police when there was probable cause for the arrest. (Ricky Carioti/The Washington Post)

Some legal questions are knotty enough that the Supreme Court can’t decide them on the first try. Or the second.

And, after Monday’s oral argument over a familiar problem, there was reason to believe that the third time might not be the charm, either.

The issue is whether someone who believes he was arrested in violation of his free speech rights can pursue a claim of retaliation against the police when there was probable cause for the arrest.

Justice Samuel A. Alito Jr. presented the dilemma that faced the court.

On the one hand, suppose a police officer makes an arrest in the heat of the moment in perhaps a dangerous situation where threats are exchanged. No one wants the officer regularly hauled into court to defend himself against charges that the arrest was because the person mouthed off, Alito said.

On the other hand, Alito imagined a journalist who writes a critical story about the police department. He soon finds himself being pulled over for going 30 mph in a 25-mph zone.

The probable cause rule would be good for the first case, Alito said, but a problem for the second.

Which of these unattractive outcomes should we accept? he asked.

Alaska Assistant Attorney General Dario Borghesan was representing a state trooper being sued for a 2014 arrest made at a festival called Arctic Man. (Chief Justice John G. Roberts Jr. described the scene as “10,000 mostly drunk people in the middle of nowhere and you’ve got eight police officers.”)

Borghesan said the rule about dismissing a suit when there were reasonable grounds for the arrest is the only workable rule.

He was supported by the Department of Justice. Claims of retaliatory arrest are “easy to allege and difficult and expensive to defend against,” said Deputy Solicitor General Jeffrey B. Wall.

But the justices weren’t so sure.

Justice Elena Kagan imagined the police officer who “decides to arrest for jaywalking somebody wearing a Black Lives Matter T-shirt or, alternatively, a Make America Great Again cap.” There are lots of laws police do not actively enforce, she said.

“It makes no difference to the First Amendment that there might have been probable cause for an arrest if, in fact, the arrest occurred as a result of retaliation for protected speech,” she said.

But as in the past, the justices bogged down in trying do decide exactly how a judge should know which cases should be nipped in the bud and which should proceed to a trial.

The court faced the same question last term, and it found a way to punt. Fane Lozman sued the Riviera Beach, Fla., city council because he was arrested at a council meeting for refusing to stop talking during a public comments portion of the meeting.

He faced charges of “disorderly conduct” and “resisting arrest without violence,” but the charges were dropped. Still, lower courts refused to let his case go forward because there was probable cause for the arrest under an obscure Florida law.

The Supreme Court ruled 8 to 1 that a plaintiff can bring a retaliatory arrest claim if he can prove the arrest was the result of an official municipal policy of intimidation.

The court ruled in 2006 that a person pursing a retaliatory prosecution case has to prove the absence of probable cause. But the question of retaliatory arrest has proved harder to decide.

The case now before the court is Nieves v. Bartlett.