A change of plea hearing has been scheduled for Monday in federal court for Joel Greenberg, the former Seminole County tax collector who resigned in disgrace last June in a case that has reportedly since taken aim at his friend and ally U.S. Rep. Matt Gaetz.
Greenberg — who is required to attend the 10 a.m. hearing before U.S. Magistrate Judge Leslie Hoffman — is expected to plead guilty to federal charges as part of an agreement with prosecutors with the U.S. Attorney’s Office.
Details of the agreement have not yet been revealed, including whether he has agreed to testify against Gaetz, who is under federal investigation for accusations that he had sex with a 17-year-old girl.
Greenberg had been speaking to federal investigators since last fall and told them that he paid for sexual encounters involving himself and Gaetz, according to a New York Times report. Investigators have also been looking into whether the Republican congressman from Florida’s Panhandle paid for sex and travel with women Greenberg recruited online.
Gaetz has not been charged with any crime, and he has repeatedly denied any illegal activity, including that he paid for sex or had sex with anyone underage.
“The first indictment of Joel Greenberg alleges that he accused another man of sex with a minor for his own gain,” said Harlan Hill, a Gaetz spokesman, in an email to the Sentinel. “That man was apparently innocent. So is Congressman Gaetz.”
Still, news of Greenberg’s intent to change his plea comes days after a CNN report indicated that federal investigators assigned to the Gaetz probe were seeking to firm up the cooperation of Greenberg and a former Capitol Hill intern who dated Gaetz.
The report also indicated that investigators were “nearly finished” collecting evidence, with a charging decision “likely to take some time” and expected to be made by prosecutors in the Justice Department’s public integrity section.
If he is found to have had solicited sex with a minor, Gaetz could be prosecuted under the same federal child trafficking law as Greenberg. He also could be charged under the Mann Act, which bans bringing anyone across state or international lines for the purpose of prostitution, legal experts said.
Greenberg allegedly confirmed in a confession letter last year — written on the advice of notorious political operative Roger Stone, in an effort to seek a pardon from then-President Donald Trump — that he and Gaetz had sex with the girl before she was 18, according to a report by the Daily Beast.
According to the report, Greenberg wrote that he and Gaetz believed at the time that the girl was 19, but learned from an anonymous tip on Sept. 4, 2017, that she was underage.
“Immediately I called the congressman and warned him to stay clear of this person and informed him she was underage,” Greenberg reportedly wrote. “He was equally shocked and disturbed by this revelation.”
Under the Mann Act, there are “limited circumstances” in which defendants can argue that they reasonably but incorrectly believed a minor was 18 or older, according to Bruce Udolf, a Fort Lauderdale defense attorney and former federal prosecutor.
“That could be a hurdle the prosecution would have to overcome,” he said.
Greenberg and Gaetz reportedly used mobile payment apps like Venmo to pay the recruited women, describing it sometimes as “tuition” or “school.” Prosecutors would have to prove these payments were for sex, not just part of a relationship, Udolf said.
The attorney pointed to another Daily Beast report of an alleged $900 payment from Gaetz to Greenberg, who sent payments that totaled the same amount of money to three women hours later.
“If that is the case, it’s more problematic,” he said. “It suggests less of a sugar daddy relationship and more of a transaction that involves paying for sex.”
Whether he cooperates against Gaetz, Greenberg’s plea marks a final chapter of the former tax collector’s stunning rise in Florida Republican politics and sudden downfall.
Greenberg won the tax collector’s job at the age of 31 and without a college degree after defeating longtime incumbent Ray Valdes in the 2016 Republican primary and then beating a no-name candidate in the general election.
But soon after taking office, he became involved in one controversy after another — including using millions of dollars in taxpayer funds to hand out lucrative contracts to friends, business partners and political associates.
He banned a county commissioner from entering the county’s tax collector’s offices. He set up a Blockchain business within his government office. He armed many of his top-level managers with firearms, and even Greenberg, himself, often walked around in public with a pistol to his side.
He pulled over a woman for speeding while wearing a badge. He pitched an unpopular plan — that was rejected by state officials — to sell off the branch offices of the Tax Collector’s Office and then use the money to buy run-down shopping centers.
But last June, Greenberg was arrested at his home in the upscale Heathrow community after a grand jury indictment charged him with stalking and unlawful use of ID. Federal prosecutors said Greenberg sent fake letters to a private school from a “very concerned student” that accused teacher and political opponent Brian Beute of sexually abusing a student repeatedly.
Greenberg is also alleged to have created fake Facebook and Twitter accounts that were made to appear to belong to Beute.
Investigators said they later found Greenberg’s DNA and fingerprints on the letters, and the IP address from the fake social media accounts was traced back to Greenberg’s home address.
During that raid at his home on June 23, federal agents found several stolen IDs inside a backpack in his work vehicle, along with a pair of fakes in his wallet.
Under three more grand jury indictments that followed, Greenberg was charged with using equipment in his public office to create fake IDs by putting his photo with the personal information of other people.
He also is accused of soliciting a girl between the ages of 14 and 17 for sex, wire fraud, illegal money transactions, conspiracy to bribe a public official, and theft of government property.
The magnitude of the case against Greenberg and the nature of his alleged crimes creates obvious liabilities regarding his credibility as a witness, according to Patrick Cotter, a former federal prosecutor who now works as a defense attorney in Chicago.
“If it’s true, he’s a self-confessed sex trafficker,” Cotter said. “He’s a self-confessed guy who frames other people for molesting children. … To call him a flawed witness is to be kind — I mean, he is a mess.”
Prosecutors could overcome Greenberg’s credibility problem, though, with evidence that corroborates the former tax collector’s testimony, like hotel receipts, plane tickets, phone records and other financial documentation, said Stephen Saltzburg, a law professor at George Washington University and former deputy assistant attorney general.
“A woman who comes forward and basically testifies that [Gaetz] paid for her travel and she had sex, that person is going to be more believable probably than Greenberg,” he said.
mcomas@orlandosentinel.com; mcordeiro@orlandosentinel.com
