The U.S. Justice Department reportedly is investigating Gaetz’s alleged sexual relationship with a girl who was 17 years old when the affair took place about two years ago.

The investigation, anonymous officials told The New York Times, stemmed from a federal probe of Greenberg, a friend and political ally of Gaetz. Among an array of charges, Greenberg has been indicted for stalking a political rival, sex trafficking of a child, illegally obtaining information from Florida state databases and identity theft.

So Greenberg has made plenty of headlines considering his sole public role has been tax collector for Seminole County from 2017 until last year, when he resigned because of the indictments.

Scott Maxwell, a columnist for the Orlando Sentinel, said on Twitter after The Times story broke that Greenberg has kept the paper busy, posting a long list of headlines related to his escapades alleged and otherwise. (Sample: “Editorial: Good riddance to Joel Greenberg, Central Florida’s worst politician.”)

Here (from the Orlando Sentinel and others) is a sampling:

Gaetz and Greenberg are close — but just how close?

The Times said it’s not clear how Greenberg, 35, got to know Gaetz, 38. Gaetz represents the Panhandle in northwest Florida, while Greenberg’s Seminole County is in the state’s center.

Greenberg has posted at least two selfies on Twitter with Gaetz. One is from 2017 with Roger Stone, the adviser to President Donald Trump who has his own history of legal imbroglios. The other, from 2019, is at the White House with Chris Dorworth, a former Florida state representative. The same day, Greenberg posted a photo of Gaetz, Trump and first lady Melania Trump with Gaetz holding Greenberg’s daughter.

In 2018, Gaetz predicted that Greenberg would one day be a great member of Congress, The Times said. According to the Orlando Sentinel, Gaetz gave $1,000 to Greenberg’s reelection campaign last year.

That same year, the Republican Jewish Coalition called on Gaetz to acknowledge his gaffe in inviting a Holocaust denier to attend Trump’s State of the Union address. 

But then, Greenberg knows the risks of keeping controversial company. Another selfie he posted in 2017 is with Milo Yiannopoulos, the far-right activist infamous for a long article in Breitbart whitewashing white supremacists.

“Friday the 13th with Milo Yiannopoulos,” he wrote. “What could go wrong?”

Greenberg has angered Orlando’s Jews.

Greenberg drew fire in 2018 when he peddled Islamophobia on Facebook. 

“Name just ONE society in the developed world that has benefited in ANY WAY from the introduction of more Muslims,” Greenberg said. “Just one.”

Ben Friedman, the director of community relations for Orlando’s Jewish federation, said Greenberg’s question was “disgraceful” and that Greenberg was, basically, a shanda.

“I am frequently called on to speak on behalf of the Jewish community,” Friedman wrote in a Sentinel op-ed. “It’s tough — consensus can be difficult to find — but in this case, I can confidently say that Greenberg’s hateful rhetoric does not represent the Jewish community. The vast majority of Jews in Central Florida appreciate our Muslim brothers and sisters and value our shared American experience.”

Friedman made it clear the sooner he didn’t have to deal with Greenberg the better.

“The people of Seminole County deserve better than this. Greenberg’s actions are an embarrassment to the office he holds, and his attitude reflects poorly on the people who elected him and pay his $150,000 per year salary,” the Jewish leader said.

Greenberg comes from dental money …

Greenberg is the son of Andrew Greenberg, who in the 1980s founded an empire, Greenberg Dental, which now has over 90 practices across Florida. Joel Greenberg is a millionaire, mostly because of his stake in the dental practice. 

Defending himself in 2018 against the Islamophobia charge, Greenberg said that one of his brothers is Black.

“One of my best friends is Muslim, and I have a Black brother,” Greenberg told the Orlando Weekly.  “I’m Jewish, which is probably one of the most hated groups. I don’t go out there to be a demagogue against anyone else. I think it’s fun to have a discussion.” 

His Facebook page features an undated photo of himself at the Western Wall.

And he has expensive tastes.

Audits show that Greenberg used public funds to pay for $384,000 in “body armor, unspecified weapons, ammunition, as well as a drone with thermal imaging capabilities,” News13, a local broadcaster, reported. He spent at least $2.65 million on a security force and for consultants; staffers could not say what the consultants did. Three of the people on the payroll were in his wedding party.

He spent $90,000 of agency money to set up cryptocurrency mining devices, and $15,000 on a sprinkler system that was calibrated to drive away petitioners. 

On separate occasions, Greenberg used his tax collector badge to stop a woman he said was speeding and to try and persuade a traffic cop not to ticket him for speeding.

He has mother-in-law issues.

Greenberg broke parole this month when he figured out his wife had decamped from their home to her mother’s house 2 1/2 hours away. Greenberg’s mother-in-law emphatically told police he was unwelcome. He’s back in jail as a result.

He employs the Roger Stone method.

In 2016, then 31, Greenberg used his own money to run a successful Republican primary challenge that accused the 28-year incumbent, Ray Valdes, then 78, of being out of touch. 

Greenberg got support in both his campaigns from a Facebook page, Central Florida Post, founded by Jacob Engels, who has been named as an associate of Roger Stone. The page has promoted among others the Proud Boys, a far-right group also associated with Stone. 

Engels, according to the Sentinel, engaged in the same political “dirty tricks” that has been Stone’s specialty since the Nixon presidency: In 2016 he filed a report accusing Valdes of assault, but the prosecutor said Engels was only seeking a confrontation. 

Last year, the page posted an attack on Greenberg’s primary opponent itled “Creepy Brian Beute.” (Facebook has taken down the page.)

The stalking charge against Greenberg alleges that he used a pseudonym to send letters to the middle school where Beute is a teacher, falsely claiming that Beute had a sexual relationship with a student. Greenberg allegedly set up a fake Facebook page making the same charge and set up a fake Twitter account in Beute’s name promoting white supremacy.

The second indictment against Greenberg alleges that he trafficked a minor female aged between 14 and 18, and used state databases to illegally obtain information about her and others. It also alleges that he produced a fake driver’s license.

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