He's belittled City Manager Mac Craig's 29-year Army career. He's called Largo leaderless. He's accused Craig of following Hitler's tactics.
But this time, three high-ranking city staffers say he's gone too far.
Now, Leo Coughlin, who writes for the weekly Clearwater Gazette, has claimed "Largo, pound for pound, is probably the most corrupt city in America."
Craig, Assistant City Manager Henry Schubert and finance director Kim Adams are threatening to sue Coughlin, the Gazette and its editor if the paper doesn't publish an "immediate retraction and apology" to them, according to a letter written by their lawyer, Alan Zimmet.
"There's no corruption in the city of Largo," Craig said. "His article is an outright lie."
The Nov. 19 story and another by Coughlin a week earlier attack Craig's integrity and discredit all of the city's upper management, Craig said.
"I think Mr. Coughlin needs to check his facts before he makes allegations he can't support," said Adams, who has worked 22 years for Largo.
Zimmet, Largo's city attorney, is handling the matter. But the men, not the city, are footing the bill, they say.
They also dispute comments that claim the city's plans to borrow money to build a new community center were a "carefully hidden secret," according to the letter sent to the Gazette last week.
Schubert said borrowing for the center was mentioned in seven city documents, including the last two city budgets.
Sandy Pollick, Gazette editor, said she hasn't received the letter. The paper moved in January and the letter was sent to a former post office box, she said.
"I would have to see the letter before I would comment on it," said Pollick, who declined a reporter's offer to send her the correspondence.
Three phone messages were left for Coughlin on Monday and Tuesday. The Times also e-mailed a request for comment on Tuesday, but received no response.
Florence Snyder, a First Amendment lawyer in Tallahassee, reviewed the articles and the letter and said she didn't see much of a case if the men sue.
"This is America. We are allowed to call our overlords venal, corrupt and stupid," Snyder said.
Commissioner Curtis Holmes said Coughlin, 76, has a right to criticize the city.
"That's a man's opinion," said Holmes, who was championed in Coughlin's stories during the recent election.
But Zimmet said the corruption comment was framed not as an opinion, but as fact. It was preceded by the phrase "so many observers already know."
Zimmet acknowledged that public officials have a greater challenge in proving libel. They must show that the statements were both defamatory and made with reckless disregard for the truth.
"We believe he made those statements with total reckless disregard for the actual facts," Zimmet said.
Coughlin regularly writes a column called "Around Here." But he doesn't attend City Commission meetings and several officials say they haven't seen him in years. His residential phone number, which was also registered to his former blog, is listed in Baltimore County, Md.
From late 2007 through early this year, Coughlin's stories and columns were absent from the Gazette. During that time, he created a blog called LeoReports, which also featured controversial material.
In an April 2008 blog, for example, Coughlin complained about racial divisiveness in America, saying the "chief perpetrators" were African-Americans.
"There is no pleasing these people who constitute less than 15 percent of the U.S. population but want to have the chief say about everything," Coughlin wrote.
After Craig refused to put Coughlin on the city's press distribution list last year, Coughlin wrote a blog, claiming "Craig's method is exactly that followed by Adolf Hitler, Josef Stalin and Fidel Castro."
Craig said he did so because Coughlin was not affiliated with any local paper.
He commonly refers to the St. Petersburg Times as the BP for big paper. Coughlin also worked for a big paper, the Baltimore Sun, where he was foreign editor in the 1970s. He was also the Sun's Perspective section editor before resigning in 1983, and later worked as a copy editor for Aegis, a weekly newspaper owned by the Baltimore Sun, the paper reported.
Ironically, the man accusing the city of impropriety has at least one black mark of his own.
In 1993, Coughlin was convicted of fraudulent misappropriation by a fiduciary, Harford County, Md., Circuit Court records show.
Coughlin, then 60, and a business partner unlawfully spent more than $370,000 of investors' money, authorities said. The men were officers of a company called Valco International and collected money from investors to develop and market a device that prevented drunken drivers from starting a car, but the device, called Drunkguard, was never manufactured by the company, according to the Sun.
Coughlin pleaded guilty and was sentenced in 1994 to five years with all but 10 months suspended, records show. He was also ordered to pay restitution and sentenced to five years' probation.
The prosecutor, Norman L. Smith, a former assistant attorney general who now works in private practice in Baltimore, said the sentence was relatively severe and not unusual "for those type of white-collar crimes."