But last June his reputation fell apart in spectacular fashion when federal investigators arrested him on stalking and child sex trafficking charges, prompting his resignation.
On Tuesday, the case against Greenberg, 36, gained national prominence after the New York Times reported that it had also sparked a separate criminal investigation into allegations that Gaetz had a sexual relationship with a teenage girl.
The Justice Department is investigating allegations that Gaetz had a sexual relationship with a 17-year-old girl and paid for her to travel across state lines, The Washington Post reported Tuesday. Gaetz confirmed the inquiry in an interview with Axios, but has said the allegations are an attempt to extort his family. The FBI is separately investigating the extortion claim, The Post reported.
It’s unclear exactly how Greenberg’s criminal case is connected to the Gaetz investigation; Greenberg’s lawyers did not immediately respond to messages from The Post. But it is clear that the two men, who posed for a photo together outside the White House in 2019, had ties in Florida, where they both first gained power in the GOP around 2016.
Greenberg’s entire stint in office was tumultuous, with both high-profile political battles and repeated scandals marring his tenure in Seminole County in Central Florida near Orlando.
In 2016, Greenberg — who owned an Orlando-based advertising company before running for office — rose to local prominence by defeating a three-decade incumbent in the Republican primary for Seminole County tax collector. His opponent had been embroiled in controversy over questionable but legal real estate practices he and his family members had engaged in, the Orlando Sentinel reported at the time.
“People are sick of crony capitalism and with politicians using their offices for political gain,” Greenberg said after winning the primary.
Shortly after his victory, Greenberg made headlines again as he pushed for his deputy tax collectors to be allowed to carry guns to work — a move opposed by then-attorney general Pam Bondi (R). He began wearing his tax collector badge around his neck like a police official, and in December 2017, flashed the badge to pull over a woman and accuse her of speeding, WESH reported. A month later, he used his title while trying to sway an actual police officer who stopped him for driving 39 mph in a 25 mph zone.
“If there’s any way on earth — I’m just trying to stay off the front page of the damn newspaper: ‘Tax collector gets ticket.’ This is the kind of political crap I have to deal with,” Greenberg said in a plea captured on a police body camera. He got the ticket anyway.
Greenberg also navigated a political quagmire after the Orlando Sentinel reported he had inappropriately funneled $3.5 million of taxpayer dollars to his friends, including three men who were in his wedding party.
An independent audit conducted for the county also found he had used public funds to buy body armor, weapons, ammunition and a drone. He also purchased a $90,000 server room to benefit a cryptocurrency company he created. Those servers overloaded a circuit breaker inside a county building, sparking a fire that caused $6,700 in damages that weren’t covered by insurance, the audit said.
Last summer, Greenberg’s political career came to a crashing halt with federal charges. On June 23, federal officers raided his home in Heathrow, Fla., and arrested the tax collector on charges that he had stalked a political adversary. He resigned the next day.
The federal investigators said Greenberg had posed as a “very concerned student” in anonymous letters sent to the school where the political rival worked as a teacher. The letters accused the teacher of having inappropriate sexual contact with a student. The tax collector also created impostor Facebook and Twitter accounts made to look like they belonged to the teacher and wrote posts that portrayed his adversary as a “segregationist and in favor of white supremacy,” the indictment said. (Greenberg himself had a documented history of posting anti-Muslim rhetoric, as Orlando Weekly reported in 2018.)
In August, federal investigators added charges that Greenberg had used his government position to commit identity theft and accused him of sex trafficking a child.
Investigators said they found several fake IDs inside Greenberg’s home and accused the tax collector of improperly accessing a state database to access personal information of people he was in “sugar daddy” relationships with, including a minor victim between the ages of 14 and 17. Greenberg allegedly made the fake IDs to help “facilitate his efforts to engage in commercial sex acts,” according to the indictment.
Greenberg was released on bond to await his trial, but was taken into custody again in early March after he violated the conditions of his pretrial release by leaving his home after curfew to search for his wife, who told police she had left to “take a break from the stressful situation with Joel.”
He allegedly used his wife’s Snapchat account to track her location and showed up at his mother-in-law’s home uninvited around 5 a.m. His mother-in-law called the police, and Greenberg was arrested in Seminole County.
According to court records, a judge ruled Greenberg should remain in detention until his trial in June.