At a status conference in Greenberg’s case on Thursday, federal prosecutor Roger Handberg told a judge that he expected a plea, though negotiations are ongoing. Fritz Scheller, an attorney for Greenberg, asked the judge to set a deadline of May 15 for the two sides to either reach a deal or move toward a trial in the summer.
It was not immediately clear how far the negotiations had gotten, or to what extent a plea agreement would require Greenberg to cooperate with investigators, though Greenberg’s attorney hinted he was willing to share information. If prosecutors were to get Greenberg on their side as a cooperator, it is possible he could help bolster the case against Gaetz, a higher-profile target. A person who pleads guilty in a criminal case can often lessen their potential penalty by providing information that might be helpful to investigators in other matters.
Asked after the court hearing if the possible plea could spell trouble for Gaetz, Scheller said, “I’m sure Matt Gaetz is not feeling very comfortable today.” He said his client was “uniquely situated” to help prosecutors and was seeking a deal “with the least exposure possible.” He declined to say specifically what Greenberg knew.
The Justice Department has been exploring whether Greenberg procured women for Gaetz, who represents a mostly conservative district in Florida’s panhandle, and whether the two men sometimes shared sexual partners, including the 17-year-old girl at issue in Greenberg’s case.
Gaetz, known for his fierce allegiance to former president Donald Trump, would boast to people in Florida politics that he met women through Greenberg, and he also showed them videos on his phone of naked or topless women on multiple occasions, including at parties with Greenberg, people familiar with the matter have said. Like others quoted in this article, they spoke on the condition of anonymity to discuss the investigation.
After news was reported of Greenberg’s likely plea, Gaetz’s office issued a statement that it said came from “The Women of the Office of U.S. Congressman Matt Gaetz,” though it listed no names. The statement praised Gaetz’s character and disputed the allegations against him.
“In our office and under Congressman Gaetz’s leadership, women are not only respected, but have been encouraged time and time again to grow, achieve more, and ultimately, know our value,” the statement said. “On every occasion he has treated each and every one of us with respect. Thus, we uniformly reject these allegations as false.”
Gaetz’s office did not immediately respond to a request for comment on the development in Greenberg’s case.
Greenberg was a colorful political player in Seminole County, where he unseated a longtime incumbent in the race for tax collector, won a political battle to allow his deputies to carry guns on the job and flaunted his connections to prominent Republicans.
A 2019 photograph that Greenberg posted on Twitter shows him with Gaetz at the White House. He also posted a picture in 2017 of him with Gaetz and Roger Stone, another well-known political ally of Trump’s.
Prosecutors say Greenberg abused his access to a statewide database, using it to look up the personal information of people with whom he was in “sugar daddy” relationships, including the girl at the center of his sex-trafficking charge, and to help produce fake identification documents to “facilitate his efforts to engage in commercial sex acts.”
Greenberg is known to have brought Gaetz to the tax collector’s office, including during one instance when the two came to the Lake Mary Office on a weekend, according to a person familiar with the matter and a text message obtained by The Washington Post showing that Greenberg confirmed to an employee he was there with the congressman. Another set of texts appear to show Greenberg asking an employee for help getting Gaetz a replacement ID after he apparently lost his, according to a screenshot of the message.
Greenberg had previously pleaded not guilty and was scheduled to go to trial this summer. He resigned as tax collector after the first indictment against him. Brian H. Bieber, a lawyer representing the tax collector’s office, said the office had turned over materials to federal investigators and that no other employees were implicated in criminal wrongdoing.
“The result of the government’s investigation thus far has revealed not a single individual in the tax collector’s office was complicit in any of the alleged criminal conduct committed by Greenberg inside or outside of the office,” Bieber said. “We do not anticipate that changing in any way.”
In addition to exploring Gaetz’s contact with the 17-year-old, investigators have been exploring whether the congressman paid for sex with women in a way that might have violated federal sex-trafficking laws. Of particular interest, people familiar with the matter said, is a flight Gaetz took to the Bahamas in recent years with women and an Orlando hand surgeon, Jason Pirozzolo. Authorities’ interest in the flight was first reported by CBS News.
Gaetz has described Pirozzolo and his partner, Savara Hastings, as “two of my best friends.” In the congressman’s 2020 book, he described a trip to Key West on New Year’s Eve at the end of 2019, where he stayed at a home owned by Pirozzolo and Hastings and spent time with a woman he described as his date.
The two men have also bonded publicly over their mutual efforts to decriminalize marijuana. Gaetz was a keynote speaker at the 2017 conference for the American Association of Medical Marijuana, which Pirozzolo co-founded, and the doctor has praised Gaetz’s work on marijuana issues, saying they could benefit the industry.
“Congressman Matt Gaetz is in the process of working on legislation up in Washington, D.C., that will help facilitate research on the nationwide level,” Pirozzolo said in a 2018 interview with Ganjapreneur, a website that tracks the marijuana industry.
Pirozzolo, a licensed pilot, served as a fundraiser during the gubernatorial campaign for Ron DeSantis and is listed as a $50,000 donor to DeSantis on an invite to a Sept. 19, 2018, event for the Florida governor. After DeSantis (R) was elected, Gaetz pushed unsuccessfully for Pirozzolo to be appointed as the state’s surgeon general. Pirozzolo won a DeSantis appointment to the Greater Orlando Aviation Authority board in early 2019. He joined DeSantis later that year to greet Trump on the tarmac in Orlando before a campaign event.
On July 17, 2020, Pirozzolo resigned from the board, explaining in an email to the organization that his work as a physician during the pandemic required him to “focus on my family and my patients.”
Pirozzolo also earned a brief cameo in a 2020 HBO documentary “The Swamp,” which tracked Gaetz’s life as a politician. He appears briefly in a scene where Gaetz travels to the Trump International Hotel in D.C., standing by the bar with a drink in hand.
Efforts to reach Pirozzolo in recent weeks, including visits to his home and workplace, have been unsuccessful.
Gaetz has not been charged with any crimes and has denied wrongdoing, specifically disputing that he ever slept with a 17-year-old when he was an adult or paid for sex.
The charges against Greenberg initially centered only on his bid to fabricate accusations and evidence of racism and sexual misconduct against an opponent in the tax collector race, teacher Brian Beute. He now faces a 33-count indictment, giving him significant incentive to plead guilty and cooperate with investigators to help winnow potential prison time.
Asked about Gaetz in an interview, Beute noted the congressman had not been charged with any crimes.
“I don’t like seeing hearsay. And that’s not because he’s a Republican, it’s because I have a great concern about these politics being weaponized and political parties weaponizing stories like this,” Beute said. “The interesting parallel here is that I was accused of something. Okay, well, indict someone then.”
If Greenberg does become a witness for the government, he would probably face significant questions about his credibility. In addition to being accused of fabricating evidence to smear his political opponent, Greenberg is charged with wire fraud and submitting false claims to get an Economic Injury Disaster Loan while he was out of jail on bond. It is possible, though, that Greenberg could turn over documents or point investigators toward other evidence that would corroborate his story.
Zapotosky and Scherer reported from Washington.