For the past week-plus, it has been clear that Rep. Matt Gaetz (R-Fla.) is not in a good spot.

After a New York Times report about a Justice Department investigation into Gaetz’s alleged relationship with an underage girl, Gaetz came out and alleged an extortion plot against him. Except even being extorted — if that were actually the case — doesn’t mean you didn’t commit a crime. Gaetz then participated in a bizarre Fox News interview in which he seemed to take pains to include host Tucker Carlson in his problems. Carlson pushed back. Since then, Gaetz has kept a lower profile. Most recently, another Times report said Gaetz had sought a blanket pardon from President Donald Trump before he left office — well before it was known that Gaetz had knowledge of such allegations.

On Thursday, though, came more significantly bad news: A Gaetz associate in the Florida Republican Party — whose legal prosecution led investigators to the congressman — might be about to cop a plea.

A Florida politician at the center of an investigation into Rep. Matt Gaetz is negotiating with federal prosecutors to resolve his own sex-trafficking and other charges, a potentially ominous sign for Gaetz if his associate decides to cooperate in a bid for leniency.
Joel Greenberg, the former tax collector for Seminole County, Fla., was initially charged last summer in a bare-bones indictment that prosecutors have since superseded, adding charges of sex trafficking of a minor, stealing from the tax office and even trying to use fraud to get coronavirus relief money while out on bond. In the course of the investigation into his conduct, people familiar with the matter have said, federal authorities came across evidence that Gaetz (R-Fla.) might have committed a crime and launched a separate investigation into him.
At a status conference in Greenberg’s case on Thursday, federal prosecutor Roger Handberg told a judge that he expected a plea, though negotiations are ongoing. Fritz Scheller, an attorney for Greenberg, asked the judge to set a deadline of May 15 for the two sides to either reach a deal or move toward a trial in the summer.

Perhaps even more ominous for Gaetz were the comments of Greenberg’s lawyer.

“I’m sure Matt Gaetz is not feeling very comfortable today, all right?” Fritz Scheller said. When asked whether Greenberg had introduced Gaetz to underage girls for sex, Scheller admitted he was going to ignore the question.

This is a very important point, and it shouldn’t be discounted: Both exchanges were awkward. In neither did Scheller look like he was necessarily trying to plant a seed. He could have simply stumbled into both of them. It wasn’t a terribly confidence-inspiring display from a lawyer, as the above video and link show.

But he also did little to downplay the idea that his client might cut a plea deal that could harm Gaetz — at a time when he absolutely had to know that any such comments would be interpreted as such. It’s not clear how much wisdom might be behind any effort to preview such a deal, even if that was his intent, but he, at the very least, didn’t dispute it. And he did so while representing a client who faces significantly more legal jeopardy than Gaetz appears to.

The substance of the allegations against both men is key now. Each case involves alleged sex trafficking of a minor — a crime that carries inordinate scorn relative to other crimes and even relative to its potential prison sentence.

And aside from all of that, the fact that a high-profile associate of less significant political stature than Gaetz — and whose alleged crimes are allegedly related — could be cutting a deal is significant. Whether Greenberg is deliberately throwing his ally under the bus or not, he knows plenty that is of interest to investigators in the Gaetz case. A deal means he has to talk.

It could be that Greenberg’s lawyer bungled the whole news conference. It could also be that his potential plea deal is merely aimed at watering down the charges against him and avoiding a trial. And as the Russia investigation and the deals cut by Trump allies therein showed, cooperating doesn’t necessarily spell doom for the emerging target of the investigation.

At the same time, this is a criminal probe — rather than a public report involving a president who can’t be indicted — and prosecutors will make sure the evidence is significant, if that’s part of the deal. Greenberg also has plenty on the line, and helping the Gaetz investigation is clearly in his interest.

And if you’re Gaetz, it’s hardly a welcome sign.

Update: After this piece posted Thursday, we got the latest reminder of how Greenberg could be a liability for Gaetz. The Daily Beast reports that Gaetz sent $900 to Greenberg via Venmo, at which point Greenberg then sent three young women various sums of money totaling $900. A woman whose nickname Gaetz used in describing what the money was for was 18.