ORLANDO, Fla. — As Joel Greenberg stood inside a federal courtroom pleading guilty as part of a cooperation deal with prosecutors, a plane flying outside towed a banner with an ominous message to a prominent ally of the former Seminole County tax collector: “Tick tock Matt Gaetz.”
Greenberg, who resigned from the tax collector post in disgrace after his arrest last June, on Monday pleaded guilty to six felonies, including sex trafficking of a child.
Greenberg was led into court by U.S. Marshals and appeared in a dark-colored jail jumpsuit, shackled at the wrists and ankles and flanked by two attorneys. He spoke succinctly during the hearing, responding with one or two words to questions from a magistrate judge.
“Are you pleading guilty because you are guilty?” Magistrate Judge Leslie R. Hoffman asked Greenberg.
“I am,” he replied.
In all, Greenberg faced 33 federal charges. But prosecutors will drop the other 27 counts against him. Greenberg also pleaded guilty to identity theft, stalking, wire fraud and conspiracy to bribe a public official.
He could be sentenced to at least 12 years in prison. Greenberg will be required to register as a sex offender when he is released, according to the plea agreement.
Hoffman said Greenberg’s sentencing by District Judge Gregory A. Presnell would likely be set within 75 days. The magistrate judge warned Greenberg that Presnell does not have to accept prosecutors’ sentencing recommendations. Greenberg has 14 days to file an objection to his plea deal.
Greenberg’s attorney, Fritz Scheller, said after the hearing that the U.S. attorney’s office had done a “very thorough job” in building its case. Greenberg, he said, is “on the path of redemption, rehabilitation and he has a great deal of remorse.”
Greenberg’s cooperation with federal authorities will be a factor in his sentence, and prosecutors could also seek a sentence reduction later if he continues to cooperate after sentencing.
The agreement specifies that Greenberg will have to cooperate with any investigation by prosecutors.
It has been reported that federal authorities are looking into whether Gaetz, a Florida congressman and friend of Greenberg’s, had sex with the same 17-year-old Greenberg was accused of trafficking or paid for sex and travel with escorts.
Gaetz has said several times that he has never paid for sex or had sex as an adult with someone underage. Gaetz’s name does not appear in Greenberg’s plea deal.
Greenberg had been meeting with federal prosecutors since last November. If the information he presents is useful and of “substantial assistance” to them, prosecutors will recommend a lower prison sentence, according to the agreement.
Scheller was unwilling to talk about the implications of Greenberg’s plea on Gaetz or other allies of the ex-tax collector.
“I guess this is must-see television and you’ll just have to wait and see,” he said.
But Scheller said that Greenberg “intends to honor” the terms of the plea agreement.
The agreement also states that Greenberg will also forfeit at least $654,780 in assets he obtained through his illegal acts.
In the agreement, Greenberg admitted to paying more than $70,000, including with his American Express card from the Tax Collector’s Office, over two years to women for sex that he met on websites. And one of the people Greenberg paid for sex was 17 years old.
Greenberg also would take old driver’s licenses turned in by residents and create fake new ones for himself. He would also offer women he paid for sex the use of driver’s licenses that he took from the Tax Collector’s Office.
Prosecutors also said that Greenberg used his public office as his personal bank account, giving himself personal loans with public money. He would then use the money to trade cryptocurrency.
The plea agreement marks one of the final chapters in Greenberg’s short but stunning political life. He won the countywide office as a 31-year-old political newcomer in 2016, defeating longtime incumbent Ray Valdes.
But on his first day in office — Jan. 3, 2017 — Greenberg began using his public position to illegally manipulate information to cover his tracks for having created a fake ID nearly two years before, according to the plea agreement.
He also handed out millions of dollars in public money to friends and political associates by creating positions for them within the Tax Collector’s Office.
He posted anti-Muslim messages on social media. He armed many of his top-level managers with firearms. And he proposed a scheme — later 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.
Greenberg filed to run for reelection in early 2020. But he was arrested and charged on June 23 and resigned a day later.
He has been held at the Orange County Jail without bond.
Monday’s hearing was attended by one of Greenberg’s victims, Brian Beute, a teacher at Trinity Preparatory School who filed to run against Greenberg for tax collector.
Authorities say Greenberg embarked on a smear campaign against Beute, sending anonymous letters to Trinity Prep falsely alleging that the teacher had sexually abused a student, while also establishing social media profiles in Beute’s name that falsely portrayed him as a white supremacist.
Beute on Monday called on Gov. Ron DeSantis to expand state oversight of tax collectors and launch an investigation into why Greenberg wasn’t held accountable sooner, despite extensive media reports of questionable spending and inappropriate conduct.
“From 2016 to 2019, prior to my campaign, the state of Florida’s oversight system was either complicit with or failed to monitor the Seminole County Tax Collector Office. Why? Who is responsible for this failure?” Beute said. “We do have an oversight issue in Florida, and it needs to be addressed.”
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(Staff writers Jeff Weiner and Jason Garcia contributed to this story.)
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