How A Rising Florida Political Player Landed Behind Bars

When failed local shock jock Joel Greenberg decided to run for Seminole County tax collector, he called out his opponent’s questionable ethics in office.

At one point, Greenberg told a local newspaper reporter he thought it was “disgusting” his opponent was “using his position to get rich” — but, after Greenberg was elected 2016, he found himself at the center of a federal investigation over allegations that he stole from his office, paid for sex with a minor and schemed against the government during a worldwide pandemic, according to CNBC's "American Greed," which returns Wednesday, Jan. 5 for its 15th season.

Greenberg, who had been considered a rising star in Florida Republican politics and even once spoke at a rally for President Donald Trump, also ensnared his former friend Rep. Matt Gaetz into the investigation — although no charges have been filed against Gaetz to date.

“There was a boldness, an in-your-face disregard for the law that went on here that I certainly had never seen in another elected office,” Michael S. Schmidt, reporter The New York Times, told the show. “[It was] just one example after another of different parts of ways of breaking the law that you didn’t think were possible.”

Greenberg hailed from a wealthy Florida family that made its fortune from a mini-empire of dental clinics throughout the state, but he was always seen as a bit of a black sheep, according to the show.

“He was brought up in a family of overachievers and that was not Joel,” Lauren Ritchie, a retired columnist with the Orlando Sentinel, said.

As a teenager, Greenberg was sent to a military academy, spent years in college — although he never graduated — and encountered some legal troubles, but his family always came to his rescue.

“The money, I think, was a problem, because it seemed like every time Joel got in trouble, somebody from the family would step forward with some cash,” Ritchie said.

Drawing on his family's wealth and resources, Greenberg set out to begin a career as a Howard Stern-type shock jock. He bought time on a local AM radio station and created “The Joel Greenberg Show” but, after a few years, he turned his focus to local politics.

Greenberg decided to run for Seminole County tax collector, the person tasked with collecting taxes and issuing driver’s and other licenses. It was a surprising career move for someone who had seemingly once craved the spotlight.

“In the hierarchy of local government, I mean the tax collector is kind of like the long snapper on the punt team,” John Horan, a former Seminole County chairman, said. “You know, he’s important, but he’s got a limited job.”

Greenberg was elected and settled into the new position in January 2017. He soon made headlines by deciding to create his own security force within the department and to allow his employees to openly carry firearms. He later received more media attention after he allegedly pulled over a woman for speeding, using just his tax collector's badge.

The county’s commissioners also started to question how Greenberg was spending taxpayer money, given his department’s high budget, as well as some newly created executive positions that came with lofty salaries and other questionable expenses. However, the commission had no legal authority over the spending, which was regulated by Florida’s Department of Revenue.

In 2019, as Greenberg was facing re-election, his unusual spending habits caught the eye of Orlando Sentinel columnist Lauren Ritchie, who revealed in an article that Greenberg had spent $3.5 million by awarding jobs and contracts to his allies.

“He was just giving out contracts to friends, three groomsmen in his wedding party, you know, people that he just ran around with,” Ritchie told “American Greed.”

An auditor would later conclude that many of the contracts had been unnecessary or vague and that those he had hired were often not needed.

Brian Beute, a local school teacher in Seminole County, decided to run against Greenberg because he wanted to “replace someone who's taking advantage of regular citizens like me,” according to Wednesday’s episode.

Yet just days after he announced his run, the school at which Beute worked received a series of a letters claiming to be from a “a very concerned student” falsely claiming that Beute had been having sex with a student. Investigators would later find Greenberg’s DNA on the envelope and handed the information off to federal authorities — who were already investigating him for his office's financial improprieties.

Greenberg was charged with stalking — and it would be just one of six different federal counts he’d later admit to as part of a plea deal.

He was also accused of using his access to the tax collector’s office to steal identities for himself and others and using that information to produce false identification cards.

As tax collector, Greenberg had also been an outspoken advocate for cryptocurrency and accepted it as a form of tax or licensure payment. Federal officials now say that Greenberg used hundreds of thousands of taxpayer cryptocurrency payments to make cryptocurrency investments to benefit himself.

“None of that cryptocurrency profit was ever returned to the tax collector’s office,” Ritchie said.

Federal prosecutors charged Greenberg with wire fraud in connection to the scheme.

Greenberg also admitted in the plea deal to sex trafficking of a child after it was revealed that he had used a popular escort service pairing “sugar daddies” with young women. In two years, authorities said Greenberg paid more than $70,000 for these women — one of whom was just 17 years old when the relationship began — to have sex with him.

“Greenberg was so out there and, for lack of a better term, open about this that he was using the credit cards he had from work to pay for some of these transactions,” Schmidt said.

Greenberg allegedly paid the women more if they agreed to take the drug ecstasy

After he was charged with stalking his opponent, Greenberg resigned from office but authorities say it wasn’t the end of his scheming. As the COVID-19 pandemic gripped the nation, Greenberg joined with a federal employee to fraudulently gain access to $432,700 in COVID-19 relief funds, according to the plea agreement.

“He is willing to go as far as to bribe someone on the inside working for the federal government to help him do that,” Schmidt said.

When he found out his applications for the relief loans had been submitted, Greenberg allegedly texted his friend “How quickly can I blow this on p---y,” according to “American Greed.”

Greenberg agreed to plead guilty to six of the counts against him in May. Prosecutors have said he is facing at least 12 years behind bars, but he has yet to be sentenced and is said to be cooperating with authorities.

To learn more, tune in to “American Greed” at 10 pm ET/PT Wednesday on CNBC.