The Strange Friendship That May Bring Down Matt Gaetz
Rep. Matt Gaetz is in the midst of one of the ugliest falls from political grace in decades. But, on a smaller and less public scale, Gaetz’s plummet largely mirrors one of his closest allies—the man who may have kickstarted his downfall: Joel Greenberg.
Gaetz, the Florida Republican, and Greenberg are friends. Until recently, both were wealthy players in the new Trumpist wave washing over the Florida GOP. Both were sons of successful fathers who made their names known across the state. Both hung out in the same circles, championed the same libertarian causes, and latched themselves onto the same Florida GOP icons, like Gov. Ron DeSantis and political operative Roger Stone.
And now, both have been ensnared in a federal probe looking into accusations that they recruited young women and paid them for sex, according to The New York Times.
As The Daily Beast reported on Friday, it was text messages about Gaetz and Greenberg’s off-hours trips to a government office that alerted investigators to the congressman’s involvement in alleged crimes—and eventually led them to what they determined to be a criminal sex ring.
But before Joel Greenberg was indicted for sex trafficking and directing attention to Gaetz, Greenberg was an eccentric tax collector with a political future and all the right connections.
Like Gaetz, Greenberg is the son of a wealthy local businessman. Dr. Andrew Greenberg co-founded a dental company with 92 offices across the state. Joel, who holds a stake in that company, went on to establish his own advertising agency, DG3. For a time, he also hosted “The Joel Greenberg Show,” a sports-themed talk radio show on WRSO 810 AM. He sold the ad company in 2015 and ran the next year for Seminole County tax collector, defeating the 78-year-old who had held the office since 1988.
Once in office, Greenberg immediately took outlandish steps for what should have been a low-profile and boring job. He moved the agency out of its rent-free government offices. He hired his friends. He handed out questionable contracts to longtime associates. He used his tax collector “badge” to pose as law enforcement and pull over a speeder. He even tried to get some tax employees to carry guns.
But it was another type of alleged abuse of power that would eventually rope in his friend, Matt Gaetz.
Greenberg, whose government agency was tasked with shredding expired drivers licenses, was illegally creating fake IDs, according to investigators. And Gaetz was with him when the pair was caught on surveillance footage visiting the Lake Mary branch of the tax collector’s office on a weekend in April 2018, according to several people with knowledge of the incident.
When asked by an employee if he had visited the office over the weekend, Greenberg responded via text: “Yes I was showing congressman Gaetz what our operation looked like. Did I leave something on?”
Images of text messages obtained by The Daily Beast show that Greenberg involved the congressman even further with a personal favor in September that year. That’s when he went outside of official protocol and directed an employee—on a Sunday afternoon—to quickly produce Gaetz a duplicate ID.
“Amy- is there anyway to assist one of our Congressmen in getting an emergency replacement ID or DL by Tuesday 2pm? His was lost yesterday and he’s got a flight Tuesday. Doesn’t have any other form of ID currently on him. Sorry to bother you on Sunday,” Greenberg wrote.
The favor was for his friend: “Matthew Louis Gaetz II,” born on May 7, 1982.
Those text messages made their way in early 2020 to the U.S. Secret Service, Florida Department of Law Enforcement, and most recently, another federal agency, according to a source with knowledge of agents’ requests.
In the years before these incidents, Gaetz and Greenberg had publicly displayed a bond that referenced their similar thinking, interests, and friendship. Gaetz, the son of a former president of the Florida State Senate, climbed to the upper tier of Florida state politics at a young age.
But he gained an unsavory reputation, even among fellow Republicans, for allegedly creating what one legislator called a sex game where “members of the FL House got ‘points’ for sleeping with aides, interns, lobbyists and married legislators.” Sources in Tallahassee told reporters that Gaetz frequented a restaurant popular with local college kids, part of his attempts to pick up undergrads.
Greenberg’s personal history during that period is much more obscure. It’s unclear when his friendship with Gaetz began, but by July 8, 2017, the two each shared a picture of their dinner with Roger Stone.
Gaetz repeatedly called Greenberg his friend, whether it was to support the tax collector’s idea to accept bitcoin, share his op-eds, or make inside jokes about their mutual lobbyist friend, Chris Dorworth.
By 2018, Greenberg was telling BuzzFeed News that Gaetz was his political mentor, an article Gaetz reposted in full on his official congressional website. Both of them visited the American Israel Public Affairs Committee that year, where they snapped a selfie with a 21-year-old woman who worked on Ron DeSantis’s campaign for Florida governor.
They’ve both pushed for marijuana legalization as well. In January 2019, Gaetz shared a video on Twitter with Greenberg and John Morgan, an Orlando attorney who refers to himself as “Pot Daddy.” Greenberg was an avid cannabis user who frequently carried around a marijuana vape pen, said three people who saw him use it either in the tax office, at work parties, or with friends. And he became Gaetz’s go-to person for cannabis vapes, according to one of those sources.
They were close enough to mingle with family. A video posted to YouTube features a photo of Gaetz cradling Greenberg’s newborn daughter. Greenberg’s wife, Abby, shared a Facebook photo of another instance in which Gaetz held her child in front of the White House, flanked by a smiling President Donald Trump.
This week, a Florida state legislator, Rep. Anna V. Eskamani, a Democrat, told The Daily Beast about her own odd interactions with Greenberg and Gaetz, who would personally approach her—sometimes together.
“There was all this weird engagement and being friendly with me,” she said. “Matt Gaetz too. I don’t have his number. I don’t have any engagement with him. He’s tried to engage with me on Twitter. I’m very careful about any response back to him.”
She said that Greenberg would frequently text her photos reminiscing about his party-boy past, and that in 2019 he and Gaetz teamed up on what she called a “weird” voicemail, which The Daily Beast published on Friday.
“We were just chatting about you, and talking about your lovely qualities,” Greenberg said in the message, followed by Gaetz’s comment: “We think you’re the future of the Democratic Party in Florida!”
On May 4, 2018, Gaetz took to Twitter to plug a new Greenberg policy innovation. “Pay your taxes in crypto currency? @MrJoelGreenberg says yes,” wrote Gaetz, now a member of the House Blockchain Caucus. He tagged a Greenberg parody account in the tweet, possibly by mistake.
A Seminole County audit last year showed that Greenberg had funneled about $66,000 in taxpayer funds to his own company, Government Blockchain Systems LLC. When auditors asked him about the company, Greenberg told them that he had been developing a new way to accept “cryptocurrency as payments” for taxes.
That innovation resurfaced this week in the form of new federal charges. Prosecutors allege that Greenberg stole hundreds of thousands of dollars from Seminole County taxpayers and sunk it into cryptocurrency. A millionaire, Greenberg also used about $240,000 in bitcoin to jump-start his doomed 2020 re-election bid.
Although Greenberg has never financially backed Gaetz’s federal campaign efforts, Greenberg’s parents have supported Gaetz, maxing out for him in the 2018 GOP primary. A year later, on June 9, 2020, Gaetz returned the favor, maxing out to Greenberg’s re-election.
Two weeks later, Greenberg was hit with his first indictment, on charges of stalking his Republican political opponent.
Prosecutors have vastly expanded those charges to a diverse list of crimes, ranging from wire fraud to sex trafficking, alleging that Greenberg had recruited at least one teenager between 14 and 17 years old to engage in a “commercial sex act” in 2017, in Central Florida and elsewhere.
That’s where Gaetz comes back in.
The New York Times revealed on Tuesday that federal investigators were also looking into whether Gaetz violated sex trafficking laws in his relations with an unnamed 17-year-old girl. The teen is allegedly the same victim at the center of the charges against Greenberg.
Follow-up reports from various outlets allege that Gaetz shared naked photos of his sexual partners on the House floor, induced underage women to have sex with his friends, and tapped ATMs, Apple Pay and Cash App to pay for sex, leaving a trail of receipts. Some of the men and women involved reportedly took ecstasy for the encounters.
Gaetz’s reputation in Congress hasn’t helped him refute these allegations. It’s well-known that Gaetz tended to date younger women, often in their early twenties, and had a prolonged relationship with a congressional intern just over the age of 21. CNN reported on Thursday that he was known to share nude photos of his sexual partners with other lawmakers on the House floor, and talked about having sex with them.
Lawmakers have gossiped about his drinking and drug use for years, complaining that his office often smelled like weed and speculating that his weight loss while in Congress was due to cocaine. And his adversarial relationship with his colleagues—particularly fellow Republicans that he deemed insufficiently supportive of Trump—has cost him in his search for allies willing to stick up for him and rebut a constant stream of negative stories, even as Gaetz’s claims about an extortion plot have a ring of truth to them.
Gaetz’s initial response—that he was the victim of an “organized, criminal extortion” scheme with geopolitical implications—has added a bizarre new dimension to the whole story. The convoluted production roped in a former DOJ prosecutor, a serial fraudster, and his own father, who Gaetz said wore a wire at the FBI’s direction in order to bust the crime.
Gaetz produced a document from his alleged extorters, containing the absurd inveiglement that the DOJ would drop its sex crimes investigation if Gaetz loaned them $25 million to help spring a Jewish-American held hostage in Iran. The hostage, Bob Levinson, was declared dead last year by the U.S. government.
The exposure of the pressure campaign has done little to convince Republicans in Washington to rally to Gaetz’s defense. His spokesperson quit on Friday. His political idol, Trump, has stayed mum, as have the vast majority of his fellow Republican congressmen.
“The last time I had a sexual relationship with a 17-year-old, I was 17,” Gaetz told The Daily Beast earlier in the week, one of his oddly-specific denials of the charges against him. “As for the Hill, I know I have many enemies and few friends. My support generally lies outside of Washington, D.C., and I wouldn’t have it any other way.”
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