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Rep. Matt Gaetz gives his opening statement during a House Judiciary Committee markup of the articles of impeachment against President Donald Trump on Capitol Hill in Washington on Dec. 11, 2019.

Patrick Semansky/The Associated Press

An associate of Representative Matt Gaetz’s is working toward a plea deal with federal prosecutors investigating a sex trafficking operation, potentially escalating the legal and political jeopardy facing the Florida congressman.

The revelation that a political ally of Mr. Gaetz’s, Joel Greenberg, is seeking to strike a plea deal with investigators came during a hearing Thursday at federal court in Orlando. It’s a significant step in the case and signals that Mr. Greenberg could potentially serve as a witness in the Justice Department’s investigation into Mr. Gaetz.

“I am sure Matt Gaetz is not feeling very comfortable today,” Fritz Scheller, a lawyer for Greenberg, said after the hearing.

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Federal prosecutors are examining whether Mr. Gaetz and Mr. Greenberg paid underage girls or offered them gifts in exchange for sex, according to two people familiar with the matter who spoke on condition of anonymity because they could not discuss details publicly. Mr. Gaetz has denied the allegations and insists he will not resign his seat in Congress.

A call to the congressman’s cellphone on Thursday yielded a message that he was not accepting calls at this time. He also did not respond to a text message.

When asked directly if Greenberg, a former local tax collector outside Orlando, was co-operating with prosecutors on the Mr. Gaetz case, Mr. Scheller cited attorney-client privilege. But he said Mr. Greenberg’s co-operation would likely be contingent on whether it was required by prosecutors to get a plea deal.

“If someone signs a co-operation agreement, they are required to co-operate,” Mr. Scheller told reporters outside the federal courthouse in Orlando.

Mr. Scheller also refused to answer when asked if Greenberg had any incriminating evidence against Mr. Gaetz.

“I think if Mr. Greenberg accepts a plea agreement, he will want to show his sense of remorse, which he does have, and his sense of acceptance of responsibility,” Mr. Scheller said. “He’s uniquely situated.”

Mr. Greenberg’s legal problems began last summer when he was arrested on charges of stalking a political opponent. Mr. Greenberg mailed fake letters to his opponent’s school signed by a non-existent “very concerned student” who alleged the opponent had engaged in sexual misconduct with another student, according to an indictment from last June.

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In August, 2020, Mr. Greenberg was charged with sex trafficking a girl between ages 14 and 17 and using a state database to look up information about the girl and other people with whom he was engaged in “sugar daddy” relationships, according to an indictment.

He has pleaded not guilty to the charges. Additional charges accusing Mr. Greenberg of embezzling $400,000 from the Seminole County Tax Collector’s office were added last month, according to the indictment.

Mr. Greenberg had been scheduled to go to trial in Orlando in June.

U.S. District Judge Gregory Presnell said Thursday that the trial would be pushed back to July if Mr. Greenberg is unable to reach a deal with prosecutors by the middle of next month.

Even before his arrest, Mr. Greenberg, 36, was a lightning rod for controversy.

He was elected Seminole County’s tax collector in 2016, promising to be a breath of fresh air against an incumbent who had been in office for almost three decades.

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Months after taking office in 2017, he started allowing employees to carry guns. In late 2017, he pulled over a driver for speeding while wearing a tax collector badge that resembled a police shield. Local prosecutors declined to file charges of impersonating an officer. Not long after that, Mr. Greenberg was pulled over for speeding and asked not to be issued a ticket out of “professional courtesy.” The officer declined.

In 2018, Mr. Greenberg was widely criticized for posting an anti-Muslim tweet. A year later, the Orlando Sentinel revealed that Mr. Greenberg had spent $3.5-million in consultant contracts and salaries to friends and associates, including giving a combined $644,000 to three of his groomsmen and another $677,000 to a campaign adviser.

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