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With his legal appeals exhausted, Bonn Clayton knows the time has come to write a $600 check. That's the penalty for lying about an election.

Clayton is a 76-year-old Republican activist who lives in Chanhassen, wears a cowboy hat and carries strong views about the need for his party to help elect like-minded judges.

In May 2012, Clayton tried and failed to persuade delegates at the Minnesota Republican Convention to endorse candidates for the Minnesota Supreme Court. Undeterred, he sent out an e-mail blast that October featuring the party's name and recommending three candidates.

That action landed him in trouble with his party, and then with the state of Minnesota, for violating a law prohibiting a "false claim of support" for a candidate.

Minnesota courts upheld the resulting $600 fine. Last month, the U.S. Supreme Court declined to take up his appeal.

Clayton's case demonstrates, once again, Minnesota's uneasy relationship with free expression.

This goes back to the Minnesota Constitution itself, where free speech carries an asterisk: "The liberty of the press shall forever remain inviolate, and all persons may freely speak, write and publish their sentiments on all subjects, being responsible for the abuse of such right."

Back in 1931, the landmark U.S. Supreme Court case that guaranteed freedom of the press threw out a Minnesota law that allowed the government to stop "nuisance" publications.

"As a fundamental thing, Minnesota has a bad history when it comes to free speech," said Erick Kaardal, Clayton's attorney.

Harry Niska, a Republican activist who brought the complaint against Clayton, agrees that there are "a lot of concerns" about cases that limit speech. But he said it's also important to protect the integrity of elections.

"It's been well recognized that fraud, meaning lies that are actually meant to induce people to do something, are not protected by the First Amendment in the same way [as] even innocent or even white lies," Niska said.

The ban on false claims of endorsement dates back at least 50 years. Candidates risk a fine of up to $5,000 if they wrongly say they're endorsed by the DFL or Republican Party.

These complaints don't come up often. A state lawyer estimates that the Minnesota Office of Administrative Hearings handled five of these cases in the past decade.

After the convention kerfuffle over judicial candidate endorsements, Clayton sent e-mails to 7,000 people directing them to a website, with a "voter's guide" naming three candidates. The website declared it was "Prepared and paid for by the Republican Party of Minnesota-Judicial District Republican Chairs."

Clayton altered the language somewhat after party leaders complained. But Niska decided to file a complaint after Clayton "persisted in his effort to mislead voters."

"A $600 fine for engaging in that is hardly a grave threat to free speech," Niska said.

Perhaps not.

Yet as Kaardal put it: "If you take the view he's lying, that doesn't mean the government should investigate it."

Kaardal pointed out that other cases working their way through the courts could eliminate these kinds of speech restrictions. In September, the Eighth U.S. Court of Appeals threw out a 1913 Minnesota law that criminalized false political statements about ballot questions.

Last week, Clayton was mostly taking a break from Minnesota politics while basking in the sun in Orlando, Fla. He still doesn't admit he lied in his e-mail.

So will the $600 fine chill his speech?

"Not at all," he said. "Now I've got this to complain about."

Contact James Eli Shiffer at james.shiffer@startribune.com or 612-673-4116. Read his blog at startribune.com/fulldisclosure.