ORLANDO, Fla. (AP) — A Florida politician who emerged as a central figure in the Justice Department’s sex trafficking investigation into Rep. Matt Gaetz pleaded guilty Monday to six federal charges and agreed to cooperate with prosecutors as part of a plea deal.

Joel Greenberg, a longtime associate of Gaetz’s, appeared in federal court in Orlando. He pleaded guilty to six of the nearly three dozen charges he faced, including sex trafficking of a minor, and he admitted that he had paid at least one underage girl to have sex with him and other men.

Gaetz was not mentioned in the plea agreement or during the court hearing. But Greenberg’s cooperation — as a key figure in the investigation and a close ally of Gaetz’s — may escalate the potential legal and political liability that the firebrand Republican congressman is facing.

Federal prosecutors are examining whether Gaetz and Greenberg paid underage girls and escorts or offered them gifts in exchange for sex, according to two people familiar with the matter. Investigators have also been looking at whether Gaetz and his associates tried to secure government jobs for some of the women, the people said. They are also scrutinizing Gaetz’s connections to the medical marijuana sector, including whether his associates sought to influence legislation Gaetz sponsored.

The people had knowledge of the investigation but were not allowed to publicly discuss the ongoing investigation and spoke to The Associated Press on the condition of anonymity.

Gaetz has denied the allegations and any accusation of wrongdoing and has said repeatedly he will not resign from Congress. A spokesperson for the congressman has said Gaetz “never had sex with a minor and has never paid for sex.”

During the nearly hourlong hearing Monday, Greenberg, 36, acknowledged he understood the charges he was pleading guilty to and the possible punishment he faced and told the judge he was of a sound frame of mind.

U.S. Magistrate Judge Leslie Hoffman told Greenberg that even though prosecutors may request some leniency from his sentencing judge because of his cooperation, there was no guarantee a judge would agree to the prosecutors’ recommendations and Greenberg would be unable to change his plea. No sentencing date was immediately set.

Monday’s court appearance marked the first time Greenberg has been seen in court since the Gaetz investigation blew into the public spotlight in March. Outside the courthouse, a plane flew over during the hearing pulling a banner that read: “TICK TOCK MATT GAETZ.”

After the hearing Greenberg was taken back to jail in handcuffs and shackles, wearing a dark inmate uniform and looking worn down.

“Mr. Greenberg has pleaded guilty subject to a plea agreement that has certain requirements and obligations on him, and he intends to honor them,” Fritz Scheller, Greenberg’s attorney, said after the hearing. “He definitely feels a sense of remorse.”

Asked if Gaetz should be nervous, Scheller said, “I will leave that up to Matt Gaetz’s attorneys to answer.”

As part of his plea deal, Greenberg, a Republican who served as the tax collector in Seminole County, admitted he recruited women for commercial sex acts and paid them more than $70,000 from 2016 to 2018, sometimes through online payment services like Venmo. They include at least one underage girl he paid to have sex with him and others, the plea agreement says.

Prosecutors wrote in the plea agreement that Greenberg had introduced the girl to others, who also “engaged in commercial sex acts” with her. The agreement does not identify the men.

Greenberg first met the girl online from a website where she was posing as an adult and first paid her $400 after a meeting on a boat, the documents said. He later invited her to hotels in Florida where he and others would have sex with her and supplied her and other people with ecstasy, according to the plea deal.

In total, prosecutors say Greenberg had sex with the girl at least seven times.

Greenberg’s legal scrutiny began when he was arrested last summer on charges of stalking a political opponent, Brian Beute. Prosecutors said he mailed fake letters to the school where his opponent worked, signed by a nonexistent “very concerned student,” who alleged the opponent had engaged in sexual misconduct with another student.

“I wouldn’t want to be him,” Beute, who showed up at the courthouse on Monday, said after the hearing.

Greenberg also is accused of embezzling $400,000 from the Seminole County tax collector’s office, according to the indictment filed against him.