The congressman and his wingman


Their relationship is central to the allegations against Gaetz, a fierce Donald Trump ally who denies having sexual relations with a 17-year-old and prostitutes. Together, the taxman and the congressman shared a life-in-the-fast lane existence that contradicted the staid image that most elected officials are careful to maintain.

The only-in-Florida political drama has taken one bizarre twist after another in the week since the news broke of the investigation into Gaetz. It’s a tale marked by a complicated extortion allegation involving Iran and Israel, alleged sexual crimes, a tangential cameo of a popular conservative cartoonist and even a porn star.

“You couldn’t make this story up, it’s so crazy,” said David Bear, an attorney for a Greenberg political rival whom the now-former Seminole County tax collector is accused of falsely smearing as a pedophile two years ago.

“Ultimately, it’s about abuse of power and how the Republican Party lost its way with guys like this,” Bear said. “As one of the few remaining Never Trump Republicans, nothing could make me happier than seeing Matt Gaetz and his kind being taken down. They’re the embodiment of Trumpism.”

Thirty-something scions of wealthy families, Gaetz and Greenberg were elected to their respective offices during the first Trump wave that swept Florida in 2016 and became close friends because of their shared interest in brash populist politics, cryptocurrencies and attractive young women.

The Gaetz-Greenberg relationship wasn’t one of equals, according to mutual friends, who say the tax collector looked up to the congressman. A former state legislator, Gaetz was a regular fixture on Fox who had the president’s ear. Greenberg introduced him to a handful of young women he met on SeekingArrangement, a dating website that connects attractive women with so-called sugar daddies, friends claimed. Greenberg regularly trolled the site for dates.

“Joel idolized Matt,” said one mutual friend, who declined to be named. “And since they both loved beautiful women and Joel seemed to have endless access to them, it was definitely an additional incentive for Matt to stick around. Also, Joel is one of the funnest people you can hang out with.”

The two shared more than one girlfriend, according to interviews with eight friends and associates who know the two men. Gaetz described Greenberg as a “wingman” to some acquaintances, and even promoted him as a potential congressional candidate. Now some suspect Greenberg might be cooperating with prosecutors to build a case against Gaetz.

Greenberg’s lawyer declined to comment.

Less than a year after winning office, the indictment says, Greenberg engaged in a sexual relationship with a minor and, using his special access to a federal ID system as tax collector, “obtained, disclosed, transferred, and used personal information of individuals … including individuals with whom [he] was engaged in ‘sugar daddy’…

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