Greenberg is a key target of federal prosecutors who want him to provide evidence against Gaetz in a separate case. It’s a step he appears ready to take now that the federal court in Orlando on Thursday announced a change-of-plea hearing for Greenberg scheduled for Monday.
The likely plea by Greenberg, whom Gaetz once called his “wingman,” is a new development that signals Gaetz may be facing increasing legal peril. Federal investigators have interviewed more than a dozen people in the case, according to four sources familiar with the inquiry. Two friends of Gaetz’s ex-girlfriend, who is not the 17-year-old, say she is in talks to be a witness for the prosecution but she wants an immunity deal for possible obstruction. And another source familiar with the investigation previously told POLITICO that the alleged sex-trafficking victim was “100 percent” talking to prosecutors about Gaetz, but her level of cooperation or the information she gave is not clear. The people spoke on condition of anonymity to discuss the legal proceedings.
A spokesman for Gaetz denounced the recent development, noting that Greenberg has a history of fabricating allegations of underage sex.
“The first indictment of Joel Greenberg alleges that he falsely accused another man of sex with a minor for his own gain. That man was apparently innocent. So is Congressman Gaetz,” the congressman’s spokesperson, Harlan Hill, said in a statement.
Greenberg, a former Seminole County, Fla., tax collector, has faced a series of federal indictments over the past year on charges including sex trafficking of a child, identity theft, producing fake driver’s licenses, stalking and fraud. He was also accused of making false claims against a political rival.
The latest indictment that was filed on March 30 contains 33 counts against Greenberg. It’s not clear which charges he may plead guilty to on Monday or whether prosecutors might substitute other charges as part of the plea deal. His attorney, Fritz Scheller, did not respond to a message seeking comment.
Spokespeople for the Justice Department and the U.S. Attorney’s Office in Orlando declined to comment beyond confirming the hearing is scheduled before a federal magistrate there on Monday.
Those familiar with the investigation — and Greenberg’s history — say he could be a problematic witness against Gaetz because of Greenberg’s history of lying. That’s why the potential testimony of Gaetz’s ex-girlfriend and the alleged sex-trafficking victim would be so important for prosecutors.
Gaetz’s former girlfriend
Gaetz’s ex-girlfriend, whom POLITICO is not identifying to protect her from harassment, initially met him through Greenberg and has been talking to prosecutors about an immunity deal for months, according to two sources who had discussed the issue with her. Those talks have intensified in recent days, they said. Her lawyer, Tim Jansen, would not comment.
The woman had her phone seized by federal agents in December as she went to work in Tallahassee and, her friends said, felt intimidated by them.
“You can either be on the right side of this or the wrong side of it,” an agent said, according to two of her friends.
The woman grew increasingly concerned with the investigation because she may face obstruction charges after calling the alleged 17-year-old victim and her roommate, who were friends of hers from Central Florida, multiple sources said. The woman suspected that the 17-year-old and her roommate recorded her call perhaps because they were cooperating with the federal government, her friends said. That conversation could have exposed her to an obstruction of justice charge because she was opposed to talking to the feds, the friends said.
“She’s worried about being hit with an obstruction charge, and she wants an immunity deal,” one of the friends said.
If the alleged victim, the ex-girlfriend and Greenberg all cooperate against Gaetz, the chances of him being charged with sex trafficking a minor could rise substantially, legal experts tracking the case said. POLITICO is not identifying the 17-year-old because it does not name the alleged victims of sex crimes.
According to associates of both men, Greenberg and Gaetz regularly attended parties with women, some of whom were located through sugar daddy websites such as SeekingArrangement.com.
The indictment against Greenberg says one girl he enticed to engage in a “commercial sex act” with him was under 18. Gaetz has acknowledged sometimes paying for meals and hotel rooms for women he was “dating” but has said that is commonplace.
Another potential witness
As recently as May 3, a close Gaetz associate was interviewed by federal investigators for more than two hours at an FBI office in Maitland, Fla., which is less than a 10-minute drive from Orlando. A majority of the interview focused on past parties that involved key players tied to the sex trafficking probe, including Gaetz and Greenberg, according to the Gaetz associate, who spoke on a condition of anonymity.
The person said they were unable to provide many specifics to federal investigators, but roughly 90 percent of the interview focused on past parties, drugs and social gatherings. On April 30, days before speaking with federal investigators, the Gaetz associate took a polygraph test that focused on whether the associate had any sexual contact with the alleged victim and provided the results to prosecutors to show nothing happened between the two.
Beyond the Gaetz investigation, agents also briefly questioned the Gaetz associate about a 2020 sham no-party-affiliation candidate that ran in a key Florida Senate seat as part of a scheme to siphon votes from the Democratic candidate. The race was won by state Sen. Jason Brodeur, a central Florida Republican and longtime Gaetz friend. Agents also focused briefly on marijuana policy, a longtime area of focus for Gaetz who has become one of Republicans’ biggest boosters for the industry since joining Congress.
The federal probe also includes whether a Sept. 2018 trip to the Bahamas that included five young women, including the 17-year-old key to the investigation, was an attempt by Jason Pirozzolo, a politically-connected Orlando surgeon and marijuana entrepreneur, to use the trip to get favors from Gaetz. Pirozzolo was on the trip and his private plane was one of two used on the weekend getaway.
At a hearing last month in Orlando, a prosecutor and an attorney for Greenberg told a federal judge that they expected a plea deal for Greenberg rather than a trial in his case. He faces a strong incentive to cooperate with prosecutors since the sex trafficking charge alone carries a mandatory 10-year prison term when a 17-year-old is involved.
Federal law also allows defendants to be charged and convicted even if they did not know that the victim was underage, as long as they had a reasonable opportunity to observe the person.
“Most crimes say you have to have criminal intent, this doesn’t,” said Bernie Martinez, a Texas attorney who appealed an unrelated client’s conviction under the law on the grounds that his client did not know the victim was under 18.
“The law says that if a suspect had a ‘reasonable opportunity to observe’ the victim, then it doesn’t matter if they didn’t know she was underage,” Martinez said. “If they can prove that she was 17 at the time, that’s enough to move forward with an indictment.”
Three sources familiar with the investigation say prosecutors are also examining whether other men had sexual contact with the alleged victim in the case, including an unindicted co-conspirator in an unrelated fraud case related to Greenberg and a former employee in his tax office who also had relations with the victim’s roommate.
In the latest indictment of Greenberg, which includes the sex-trafficking allegation, the former tax official was also charged with unlawfully using a state drivers license system to “obtain and disclose” personal information on the 17-year-old that he looked up on Sept. 4, 2017. She turned 18 on Dec. 20, 2017.
Greenberg made multiple fake drivers licenses for himself and used them in so-called “sugar daddy” relationships with women he met on SeekingArrangement.com and through other apps, according to the indictment and associates of his. Three sources said that, when Greenberg was first arrested in June 2020, federal agents found he was in possession of multiple fake IDs, including one that belonged to the alleged sex-trafficking victim.
Prior to that, friends said Greenberg had boasted to them about having had sex with a 17-year-old — and bragged that she then went on to work in pornography, where she still is today.
One source familiar with the investigation said Greenberg was recently moved to more secure confinement as leaks from him began surfacing in the press. Another informed source said Greenberg started asking inmates on how to strike a deal with prosecutors to avoid decades in prison.
Greenberg’s lawyer, Scheller, would not comment when asked about his client’s jail accommodations or the driver licenses he allegedly had in his possession.
The news of Greenberg’s likely plea deal was celebrated by David Bear, the lawyer of the teacher who had been falsely accused by Greenberg of being a pedophile.
“I look forward to this being the first act cleaning up the corruption that has permeated far too many of our politicians,” Bear said in an email. “The network of corrupt politicians which I expert Greenberg’s testimony to lead towards the prison gates should serve as a blinking neon light that … there are committed and ethical individuals who will stand up to their threats as well as federal prosecutors who will show them that just because they are rich and powerful does not mean that they are above the law.”