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Dear Reader,

It has now been just over a year since Joel Greenberg pled guilty and cooperated with federal prosecutors in Florida. Greenberg, it seemed, would be the star witness — deeply and disturbingly flawed, but a linchpin nonetheless — in a potential federal indictment of Congressman Matt Gaetz. Yet, a year-plus later, DOJ still hasn’t made its move. 

There’s a lot we don’t know, of course — including, most importantly, whether Gaetz will be indicted at all. But we can read the indicators and get some sense of what may be going on. In my view, while an indictment of Gaetz remains likely, there’s also genuine and growing uncertainty about whether a prosecution will ultimately be successful.

Greenberg, you’ll recall, is the former tax collector who reportedly engaged in all manner of horrible conduct with Gaetz and other Florida miscreants. Greenberg pled guilty to a slate of twisted crimes including sex trafficking of a minor, theft, fraud, and stalking. Particularly worrisome for Greenberg’s credibility moving forward, he once falsely accused a teacher who challenged him politically of having sex with an underage student. Now, Greenberg apparently is telling prosecutors that Gaetz had sex with an underage girl. It’s never good for prosecutors when your star witness has already been caught lying about the exact same type of allegation he’s making in your case. 

As a prosecutor, I built plenty of cases on testimony from cooperating witnesses who had committed vile acts. I did more than one trial where my star witness was a confessed multiple-murderer. But I’ve never had to rely on a cooperator who was so unseemly, and raised as many credibility issues, as Greenberg. Federal prosecutors in Florida no doubt recognize this, and will seek to develop independent evidence to corroborate as much of his testimony as possible. You don’t want to argue to a jury, “You should believe this fact because Joel Greenberg says it’s so.” You need to be able to argue, “You should believe this fact because other evidence shows that it’s true, and Greenberg helped explain it for you.” Greenberg needs to be a supporting character, not the lead.

The broad expectation has long been that Greenberg’s indictment and cooperation would result in criminal charges against Gaetz. That still might happen, but the passage of more than a year (and counting) is perplexing. Yes, investigations take time, and yes, prosecutors must be extra-careful when considering charges against a sitting member of Congress. But a year feels like an awfully long time, given my experience, even given the need to corroborate everything Greenberg says. Sure, prosecutors need to button up every aspect of this case — but they’ve had ample time by now to button up, tighten the belt, and cinch the suspenders. 

So when might we see a decision, one way or the other, on a Gaetz indictment? As always with these things, we don’t know for sure. (As a prosecutor, I used to treasure grand jury secrecy; now, as a media member, it’s a bummer.) We do know this: midterm elections are in early November, and DOJ has a longstanding practice not to announce politically-sensitive indictments within 60 or 90 days of an election. Different prosecutors understand the rule differently, but it’s a safe bet Garland’s DOJ will go with the longer 90-day period. That means Gaetz will be indicted either by early August, or not until after midterms, in late 2022 or into 2023. Or, of course, he might not get indicted at all.

Last week, we saw an unusual blip on the docket sheet. The judge on Greenberg’s case, who had agreed to several adjournments of sentencing, said he would not grant another delay unless prosecutors could show “extraordinary circumstances.” This is unusual because, typically, prosecutors and cooperators alike want to postpone sentencing for as long as possible, and judges reflexively sign off. I’ve had cooperators sentenced years after they pled guilty; one particularly prolific mob cooperator was sentenced six years after he began cooperating. 

Delay is usually in the interests of all parties. Prosecutors want to keep intact the cooperator’s incentive to testify and cooperate fully and truthfully; with sentencing still pending, a cooperator is less likely to go off the rails and risk punishment. The cooperator wants to be sentenced as late as possible so he gets credit from the judge for the entirety of his cooperation; judges typically reward more extensive cooperation with larger sentencing breaks. Ordinarily, judges automatically approve adjournment requests; if both parties want the delay, why not? 

Yet something plainly was bothering Greenberg’s judge, who demanded a specific and compelling explanation why further postponement was necessary. Prosecutors made enough of a showing to satisfy the judge that “extraordinary circumstances” existed. So what might those extraordinary circumstances be? 

On one hand, it could be that prosecutors convinced the judge that Greenberg’s cooperation has been so productive that they simply need more time to sift through all the information, do investigative followup, and, presumably, obtain indictments from the grand jury. But it also could mean that Greenberg’s cooperation has run into a snag and is unraveling, and prosecutors need time to regroup and figure out what to do with him next. My sense is it’s more likely the former scenario. We don’t know for sure, but I believe that if Greenberg had totally imploded, we’d know about it by now. And, in that scenario, prosecutors might not have wanted further delay, preferring instead to proceed quickly to sentencing.

Keep in mind: if Gaetz does get indicted, there will still be the not-insignificant matter of trying and convicting him. Over 90% of all federal indictments result in convictions, though the vast majority of those are the result of guilty pleas — and Gaetz seems unlikely to admit guilt, given his furious denials thus far. 

Even among federal cases that go to trial, a solid majority end up with guilty verdicts. But a Gaetz trial would be anything but typical. Start with Greenberg, as problematic a cooperating witness as you’ll ever see. If his own prior conduct — including sexual abuse of a minor — is so offensive that it turns off a single juror, then the prosecution will have a problem. 

Beyond that, Gaetz is uniquely high-profile and divisive. His detractors really, really hate him. But his supporters, and MAGA-world in general, view him as a hero. 

Gaetz would be tried in federal court in the Middle District of Florida — a politically-mixed area in a state that went for Trump in both 2016 and 2020. It’s a virtual mathematical certainty that any twelve-person jury would contain at least a handful of Trump (and Gaetz) supporters. That’s not to say a Democrat would automatically vote to convict while a Republican necessarily would favor acquittal. We’d hope that any juror would put aside political beliefs and decide the case based solely on the evidence at trial, consistent with their oath. But let’s be real: people are people, politics will enter the fray, and emotions will run hot. 

The Greenberg-Gaetz saga thus far has been fascinating and bizarre, and it’s not entirely clear where this is all headed. I do (still) think DOJ will, at some point, indict Gaetz, but that’s largely based on my old prosecutorial instinct and not verifiable fact. I know this: an indictment of Gaetz would be just the first step up a steep and treacherous hill that prosecutors must climb to win a conviction.

Stay Informed,