Within days of taking office, he fired three employees who had supported his predecessor and began spending more than $1.5 million in taxpayer money on personal expenses, including guns, ammunition, body armor and a drone, as well as on computers for his own cryptocurrency venture, a county audit later revealed.
The following year, according to The Orlando Sentinel, Mr. Greenberg posted a photograph of himself on social media with Milo Yiannopoulos, a right-wing personality who has a history of making racist remarks. The newspaper also detailed Mr. Greenberg’s own misogynist and anti-Muslim comments on Facebook.
In his bid for re-election, Mr. Greenberg turned in late 2019 to clandestine tactics to undermine a possible rival, according to court papers. Prosecutors said he sent an anonymous letter to the school where one potential candidate worked that made unfounded accusations of sexual misconduct with a student and making similar claims on a fake Facebook account.
As the primary race intensified last summer, similar messaging began appearing on fake social media accounts that have been tied to Mr. Stone.
“Watch out Seminole county,” said someone named April Goad on Facebook, warning Floridians “don’t open your door” to the rival candidate, according to Graphika, a company that specializes in analyzing social media.
The post linked to an article about the rival published on Central Florida Post, a website controlled by Mr. Stone’s associates that had written favorable articles about Mr. Greenberg. The website was founded by a member of the Proud Boys who has been linked to security providers for Mr. Stone on Jan. 6 in Washington in the lead-up to the insurrection at the Capitol.
Mr. Greenberg’s re-election efforts quickly evaporated when he was first indicted last June, and he resigned a day later.
Kitty Bennett and Susan C. Beachy contributed research.