ORLANDO — Joel Greenberg’s political career looked promising just over a year ago: He was set to run for reelection as Seminole County’s tax collector — pledging nearly half a million dollars of his Bitcoin investments to his campaign — and was even contemplating a run for Congress against U.S. Rep. Stephanie Murphy.
Having won elected office at just 31 years old in 2016, he had since expressed boredom with the job but seemed to relish his connections with people of wealth and influence, including developer and former state legislator Chris Dorworth.
But few were as visible a friend or as vocal an advocate for Greenberg — over four years of rolling controversies that earned him distinction as an iconoclast on the political right, but infamy among many on the left and center — as his friend from the Panhandle with a similar reputation, U.S. Rep. Matt Gaetz.
During an interview on WFLA News Radio in June 2017, Gaetz said Greenberg should run for Congress against Murphy. By then, both Greenberg and Murphy had been in office for just six months.
“Joel Greenberg has gone into the Seminole County Tax Collector’s Office. He’s taken it by storm,” Gaetz said. “And he’s been a disruptor … And if you look at what people want in the country right now, they want that disruptor. And they want someone who is not going to adhere to the dogma that has strangled progress in Washington, D.C., for a generation.”
Over the years that followed, Greenberg and Gaetz, a fellow Republican who represents Fort Walton Beach, were often spotted having dinner and drinks together at Seminole restaurants and bars. Former employees of the tax collector’s office said Greenberg often bragged how Gaetz visited him at his Heathrow home.
Greenberg also brought Gaetz into the tax collector’s administrative office in Lake Mary in late 2017 or early 2018, showing him around and introducing him to various employees, according to Alan Byrd, a spokesman for the office.
When Greenberg launched his reelection bid, Gaetz was the first person to donate, chipping in the personal maximum of $1,000 on June 9.
Two weeks later, Greenberg stood shackled in a federal courtroom in downtown Orlando, accused of stalking an election rival and identity theft. The federal case against Greenberg, who resigned from office the day after his initial arrest, has since ballooned.
And this week, that case, too, linked Greenberg to Gaetz, when The New York Times reported that the Panhandle congressman was being investigated for potential sex trafficking offenses — a probe that branched off from the Greenberg investigation.
Gaetz has not been charged with a crime and has denied all wrongdoing, claiming that the existence of the investigation into him was leaked to derail a separate investigation into a blackmail scheme targeting his family, with which they had been cooperating.
Today, Greenberg sits in the Orange County Jail facing 33 federal charges, including stalking, identity theft, wire fraud, bribery, theft of government property, conspiracy to bribe a public official, creating fake IDs and sex trafficking of a minor.
Talking to an Orlando Sentinel reporter last fall, by then already facing charges that could cost his freedom, he lamented the loss of his friends.
“No one wants to talk to me anymore,” he said, with his voice breaking. “You have no idea what I’ve been through, and what I’m going through now.”
Greenberg was elected in 2016 as a newcomer to Seminole County’s political scene after defeating longtime incumbent tax collector Ray Valdes in the Republican primary then beating a write-in opponent in the general.
Largely unknown at the time, but capable of self-funding his campaign as the scion of a dental empire owned by his father, Greenberg railed against Valdes for buying and selling tax-delinquent properties that are handled by the tax collector’s office.
Soon after taking office in January 2017, Greenberg redesigned and modernized the tax collector’s website and opened a new branch office in Winter Springs for rural residents in east Seminole.
But his term was quickly marred by controversies, including anti-Muslim social media posts, proposing to sell off tax collector properties, allowing his employees to openly carry guns, using his tax collector badge to pull over a speeder, using his position to try to get out of a ticket, giving lucrative contracts and positions to close friends and using his office to set up blockchain business.
Amid all that, within a couple of years of taking office, Greenberg told a Sentinel reporter that he was bored with the office because it involved too much redundancy and offered little opportunity to be creative or break out into new business ventures. State Rep. Anna Eskamani, an Orlando Democrat, also recalled Greenberg telling her he was bored with the job.
Greenberg then became active in Seminole politics.
In December 2017, he joined a group of Seminole residents pushing for a referendum to elect a countywide mayor, similar to the system in Orange County. The group also wanted county commission races to be nonpartisan, represent individual districts rather than countywide, and be limited to two-year terms. The plan eventually fizzled out.
Greenberg often mentioned to local leaders how his family was wealthy and powerful. His father, Andrew Greenberg, started Greenberg Dental in the 1980s, which now has 92 offices across Florida. However, there is no record of his family ever being involved in local politics.
According to state financial disclosure forms required from all elected officials, Joel Greenberg listed his worth at the of end of 2019 at nearly $5.9 million. That included $5.5 million worth of stock in his family’s business AWG Inc., $85,500 in jewelry and $276,000 in bank accounts.
Greenberg also soon began hob-knobbing with well-connected people — often with Gaetz at his side.
An image he posted on Twitter on July 8, 2017, showed Greenberg and Gaetz standing next to Roger Stone, the infamous Trump and Nixon associate and provocateur.
A video posted on Facebook in January 2019, shot at a get-together at Dorworth’s Heathrow home, shows Greenberg alongside Gaetz and John Morgan, the wealthy attorney and medical marijuana advocate, as they celebrated Gov. Ron DeSantis’ directive to end a ban on smokable marijuana.
That June, Greenberg’s wife, Abby Greenberg, posted a slew of photos on Facebook featuring her husband, Dorworth, his wife and Gaetz at various locations in Washington, D.C., including with the first couple at the White House and touring the Capitol Dome.
In one photo, Gaetz beamed in sunglasses as he posed in front of Donald and Melania Trump, holding Greenberg’s daughter in his arms.
In a text message to a Sentinel reporter last July, Dorworth declined to discuss his relationship with Greenberg, saying only, “Joel is a friend of mine.” Dorworth, a partner with the lobbying firm Ballard Partners, did not respond to a text message this week asking if he is still friends with Greenberg.
Eskamani, the state representative who had previously feuded with Greenberg over his anti-Muslim social media comments, recalled receiving a voice mail from Greenberg on July 4, 2019. In the recording, Greenberg said: “Hi, Anna” and then handed off the phone to Gaetz, who told her that she is the “future of the Democratic Party,” Eskamani recalled.
“It was super weird,” she said, adding that most Trump-aligned officials that day were attending Trump’s “Salute to America” celebration at the Lincoln Memorial in Washington D.C., while Gaetz was hanging out with Greenberg in Florida.
In the latest and fourth indictment filed by the U.S. attorney’s office this week, prosecutors say that Greenberg — just days after he was arrested on the initial stalking charges, which was quickly followed by his resignation from public office — restarted two of his former companies and used them to obtain more than $432,000 in fraudulent loans meant to help small businesses during the COVID-19 pandemic shutdown.
Greenberg also is accused of diverting more than $400,000 in public money from the tax collector’s office into a private bank account and into a business he set up to buy and sell cryptocurrencies and machines used to mine cryptocurrencies. An arraignment is scheduled for April 9.
Greenberg also faces charges from three previous grand jury indictments that he stalked a political opponent, illegally used a state database and old driver’s licenses to create fake IDs and sex trafficked of a minor. He has pleaded not guilty to those 14 previous charges.
His trial is scheduled for mid-June in federal court in downtown Orlando. However, that could be delayed. If convicted on all counts, he could likely face decades in federal prison.
How the investigation of Greenberg led federal authorities to also take aim at Gaetz is unclear. The New York Times report on the probe said it centered on allegations that Gaetz had a sexual relationship with a 17-year-old girl and paid for her to travel with him.
Greenberg is charged by the U.S. attorney’s office of using a confidential state database to produce false identification that facilitated his sex trafficking of a girl between the ages of 14 and 17.
No charges have been brought against Gaetz, and it’s unknown if the allegations are connected.
Orlando Sentinel staff writer Jason Garcia contributed to this report.