The former mayor of Islamorada was charged this week with conspiracy to commit tax fraud.
Michael Reckwerdt faces five years in federal prison if convicted. He is scheduled to be arraigned on Tuesday in front of a U.S. District Court magistrate in Miami.
The Wednesday charging document alleges Reckwerdt intentionally under-reported salaries paid to employees of several companies he controls in order to reduce payments to the Internal Revenue Service.
Reckwerdt, 47, owns Robbie's Marina, a popular tourist spot on Lower Matecumbe Key that offers shopping, charter fishing and tarpon feeding.
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Reckwerdt did not return phone calls for comment. His attorney, Ben Kuehne did not return text and phone messages for this story.
But last month, Kuehne told The Reporter/Keynoter that there were no "pending federal charges" against Reckwerdt.
Asked then if Reckwerdt planned on taking a plea deal, Kuehne became agitated.
"What are you possibly saying? I am not commenting on that assertion. I made a very specific statement to you," he said.
The mile marker 77 business was raided by dozens of federal agents in November 2011, but no charges were filed until Wednesday. The raid involved agents with the IRS, the U.S. Bureau of Alcohol, Tobacco, Firearms and Explosives and the FBI.
Reckwerdt also has a Robbie's location on Stock Island, which the feds also raided.
Reckwerdt briefly addressed the raids during a Nov. 10, 2011, Village Council meeting. He told colleagues and constituents that "interesting times" were ahead. He also vowed not to resign from the council, which he never did.
"I'm not going anywhere. I'm not leaving. I didn't run. I never did run," he said. "That's not what I do."
In the nearly four years that have passed since the raids, periodic check-ins with the IRS and U.S. Attorney's Office were responded to with a "neither can confirm or deny the existence of an investigation" quote.
Reckwerdt finished his final term on the Islamorada Village Council in 2012. He served for more than eight years, more than any other council member in the village's short history.
Several of Reckwerdt's former colleagues on the dais, including current Mayor Mike Forster, chose not to comment on the criminal charges filed this week.
Along with Robbie's Marina, Reckwerdt's charges involve payroll taxes at other businesses he owns, including Flamingo Air of the Florida Keys Inc., Rent-A-Boat Inc., Robbie's Charter Enterprises Inc., Robbie's Marine Enterprises Inc. and Robbie's of Key West LLC.
The IRS and the U.S. Attorney's Office would not comment when asked if more charges were pending against Reckwerdt or if any of the conspirators referenced in the charging document faced prosecution.
"The U.S. Attorney's Office will not be commenting on this matter," agency spokeswoman Annette Castillo said Friday.