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Matt Gaetz’s Wingman Paid Dozens of Young Women—and a 17-Year-Old

Jose Pagliery, Roger Sollenberger
·6-min read
Photo Illustration by The Daily Beast / Photos via Getty
Photo Illustration by The Daily Beast / Photos via Getty

As new details emerge about Rep. Matt Gaetz’s role in an alleged sex ring, The Daily Beast has obtained several documents showing that the suspected ringleader of the group, Joel Greenberg, made more than 150 Venmo payments to dozens of young women, and to a girl who was 17 at the time.

The payment from Greenberg, an accused sex trafficker, to the 17-year-old took place in June 2017. It was for $300 and, according to the memo field, was for “Food.”

Greenberg’s relationship with Gaetz, and the money Greenberg paid to women, is a focal point for the Justice Department investigation into Gaetz. And the new documents obtained by The Daily Beast—containing years of online financial transactions—establish a clear pattern: Greenberg paid multiple young women (and at least one girl) hundreds, and sometimes thousands, of dollars on Venmo in one transaction after another.

Nearly a year after Greenberg’s June 2017 payment, Gaetz Venmo’d Greenberg to “Hit up ___,” using a nickname for the teen. She was 18 years old by then, and as The Daily Beast reported, Greenberg described the payment as being for “School.”

It was one of at least 16 Venmo payments to 12 different women listed as being for “School.” Typically, the payments were for around $500, but also went higher than $1,000 in the transactions obtained by The Daily Beast.

Gaetz made only one previously unreported transaction in the newly obtained documents: a payment from the Florida congressman to the former Seminole County tax commissioner for $300 on November 1, 2018, with the love hotel emoji (“🏩”) in the memo field. The Daily Beast was unable to tie that transaction directly to any woman, but confirmed that Greenberg booked one night for that date at The Alfond Inn, a luxury hotel in Winter Park, Florida.

Greenberg—who was a close associate of Gaetz—now sits in jail after being indicted on 33 counts, including sex trafficking, conspiracy to bribe a public official, and stalking. The federal indictment claims Greenberg was “engaged in ‘sugar daddy’ relationships,” and he is said to be helping federal agents in their now-expanded investigation into the GOP congressman from the Florida panhandle.

“I'm sure Matt Gaetz is not feeling very comfortable today,” Greenberg’s lawyer, Fritz Scheller, told reporters last week.

Gaetz Paid Accused Sex Trafficker, Who Then Venmo’d Teen

According to three people with knowledge of the relationship, Gaetz was among the men who tapped Greenberg to access a large network of young women. And according to CNN, women would show up to parties at gated-community homes or hotel suites, where they would be supplied with alcohol and drugs like cocaine and ecstasy, and would have sex with the men. Greenberg would then later pay the women. (The Daily Beast has not independently confirmed these details.)

In the Venmo transactions reviewed by The Daily Beast, however, there are at least 16 payments in 2017 totaling nearly $5,000 to a woman who would later go on to date Matt Gaetz. Additionally, Greenberg paid her $1,500 over the course of two days in April 2017 using Cash App. That woman—who came to Washington, D.C. as an intern in January 2018—has said she dated Gaetz during and after her senior year in college.

Federal investigators seized Gaetz's phone in December 2020, and they took his ex-girlfriend's device shortly after, according to two people who heard the woman describe the episode. Timothy Jansen, a criminal defense lawyer representing the woman, said she is refusing to speak to journalists and declined to comment.

An examination of Greenberg’s Venmo transactions shows dozens of suspicious and curiously titled payments. Some were as simple as “Ass” or a lipstick kiss mark (“💋”). Others were more opaque, such as “Stuff” and “Orher stuff” [sic].

Three payments in the reviewed documents—in amounts of $500, $500, and $250—were designated for “Ice cream.” Five other payments were for “Salad,” one of which topped $1,000.

In the memo field for one $500 payment to a woman on Friday July 7, 2017, Greenberg used only the policewoman emoji (“👮”). County records show he had used his government-issued, taxpayer-funded American Express card at the time to cover a “weekend hotel stay” at the Four Seasons in Miami, from July 7 to July 9. And that Saturday, July 8, Gaetz and Greenberg each shared a picture of themselves at dinner with Roger Stone.

Another common payment memo was for “Food,” when Greenberg would usually pay the women $300 to $500. In one instance, Greenberg paid a woman $500 for “Food,” switched the credit card that was attached to his Venmo account, and then paid that same woman another $500 for “Appetizers” less than two minutes later.

That woman later established a formal connection in 2018 with the Seminole County tax collector’s office. According to a copy of her contract, which The Daily Beast obtained through a public records request, Greenberg agreed to pay the woman thousands of taxpayer dollars, purportedly for social media consulting and marketing.

A 2020 audit of the office, however, flagged the payments, noting that auditors did “not know what this was for.” After The Daily Beast published a story last week on Greenberg’s Venmo transactions, that woman—who is an amateur model and burgeoning Instagram influencer—went private on Instagram. A number of other women who received payments from Greenberg also appear to have recently taken steps to conceal their online relationships, most notably with other people identified in the transactions.

One of the most significant countermeasures came from the woman who was first paid by Greenberg when she was 17. The day after The Daily Beast revealed one payment Greenberg made to her after she had recently turned 18—without identifying her by name—the woman changed all of her identifying information on Venmo. She also appears to no longer be Venmo friends with two other women Greenberg paid through the app. As of this week, she also no longer appears to be Venmo friends with Gaetz.

The Strange Friendship That May Bring Down Matt Gaetz

Another woman who received repeated payments—and appears in a photo at a party with three other women also paid by Greenberg—is also no longer connected to Gaetz on Venmo.

In total, Gaetz appears to have lost at least seven Venmo “friends” in the last week, including three of the women who received payments from Greenberg. Multiple other women who received payments have also restricted public access to their Instagrams and Twitters in the last week.

Gaetz’s office did not immediately return a request for comment, and Greenberg’s attorney declined comment.

—with reporting from Matt Fuller and Adam Rawnsley.

Read more at The Daily Beast.

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