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Matt Gaetz wingman Joel Greenberg enters stunning guilty plea. Could it help Gaetz?

If Greenberg didn't spill the tea, he wouldn't have gotten a plea deal. So who will he take down?

Joel Greenberg, former Florida county tax official and friend of Rep. Matt Gaetz, pleaded guilty in federal court in Florida on Monday. His plea agreement is one for the record books: It’s 86 pages long and covers his crimes in excruciating detail, building in many incentives for Greenberg to tell the truth.

Most significantly, Monday’s guilty pleas represent the first in a long line of dominos that may begin falling in the Gaetz case.

Monday’s guilty pleas represent the first in a long line of dominos that will now begin falling in the Gaetz case.

The two main questions now are: Have the prosecutors successfully “cleaned up” Greenberg such that a future jury will believe him when he testifies about the crimes of others? And who might Greenberg’s testimony implicate?

As a career prosecutor in the courts of Washington, D.C., I negotiated countless plea agreements with defendants who decided to cooperate in our investigations and prosecutions. It’s always a difficult and delicate question whether to do business with a defendant.

The first step in the process often involves meeting with the defendant and their attorney for an “off-the-record” interview. During this interview, the defendant may get a limited form of immunity so they can tell prosecutors not only about their own criminal activity but about the criminal activity of others, without the information they provide being used against them. This allows prosecutors to determine how valuable an aspiring cooperator’s information is — in other words, who he can “give up.”

Once the defendant has debriefed, prosecutors and FBI agents investigate every scrap of information provided in an attempt to determine if it’s accurate. The unsupported word of an aspiring cooperator is worth relatively little. Indeed, the three most important words in dealing with a defendant seeking to cooperate are corroboration, corroboration and corroboration.

Nowhere is corroboration more important than in the case of Greenberg. When a prosecutor puts a cooperating defendant on the stand at the trial of others, that prosecutor is viewed as “sponsoring eww” the testimony of that witness. Put another way, given that, pursuant to our rules of ethics, prosecutors are not allowed to present false information or evidence, a prosecutor must take pains to ensure a witness is telling the truth. Given Greenberg’s track record, “cleaning him up” for the jury will be no easy task.

As a prosecutor, I sponsored the testimony of thieves, burglars, drug dealers, gunrunners and hit men. But I’m not sure I ever had a cooperating witness with as despicable a criminal resume as Greenberg’s.

The breadth, depth and depravity of Greenberg’s crimes are staggering. Looking just at the crimes to which he’s admitted, he’s been involved in sex trafficking of a child; producing a false identification document while serving as a public official — a disturbing abuse of office and of the public trust; aggravated identity theft; wire fraud; stalking a political opponent; and conspiracy to commit a crime against the United States. As a prosecutor, I sponsored the testimony of thieves, burglars, drug dealers, gunrunners and hit men. But I’m not sure I ever had a cooperating witness with as despicable a criminal resume as Greenberg’s.

The other challenge with sponsoring a guy like Greenberg is the prosecution runs the risk of a kind of “guilt by association.” When Greenberg testifies against others — let’s take Gaetz as a hypothetical example (although Gaetz has not been charged with a crime and was not mentioned in the plea agreement) — a defense attorney likely will argue to the jury something like the following: “Ladies and gentlemen, the prosecutor urges you to accept, believe and put your faith in the testimony of a man who committed sex trafficking of a child, who stalked a political opponent by falsely claiming that opponent was a child abuser and white supremacist, who abused his office and his position of public trust, who committed identity theft by using his office to gin up false documents, and so much more despicable conduct by Greenberg. This is the kind of person the prosecutors offer you in their zeal to take down a sitting congressman? Shame on the prosecutors. You should expect better from your public officials, and that goes for both Greenberg and the prosecutors who try to infect the jury with his lies.” Yes, criminal litigation is a full-contact sport.

Prosecutors face another challenge using Greenberg as a cooperating defendant. Greenberg was indicted on 33 federal felony crimes, yet the prosecutors agreed to dismiss — decline to hold him accountable for — 27 of those 33 crimes. This is yet another area ripe for defense exploitation. A defense attorney will try to convince a jury that Greenberg would lie about his own grandmother to get such a generous deal from prosecutors. They’ll suggest that Greenberg will say anything the prosecutors want him to say to enjoy the benefits of his “sweetheart” deal.

Of course, the prosecutors have ways to counter all of these tried-and-true defense tactics on a particularly challenging cooperating witness like Greenberg. Enter the 86-page plea and cooperation agreement: The plea agreement that was filed in court last week is the prosecution’s attempt to set Greenberg up to be believed by future juries.

Greenberg is fully locked in to telling the truth, the whole truth and nothing but the truth because he lies at his own peril.

The plea agreement is the longest, most comprehensive plea agreement I’ve seen in my 30 years as a prosecutor. It sets out in painstaking detail each and every crime Greenberg committed. Indeed, the "factual basis" section of the agreement spans 60 pages. The details of Greenberg’s criminal abuse of a minor, his abuse of office for personal gain and his false and defamatory attacks on a schoolteacher who had the temerity to run against him for the office of county tax collector are horrific.

The agreement also covers all incentives Greenberg has to testify truthfully against others. Prosecutors may have agreed to dismiss 27 of 33 criminal charges against him, but the plea agreement makes crystal clear that if he lies at any time in any way, including while testifying against others, then all 27 charges will be revived, and he can be prosecuted thereon.

And here’s the kicker: The statements Greenberg provided to the prosecutors during his “off-the-record” interviews about those 27 crimes can be used against him if he breaches the plea agreement by lying. Additionally, the plea agreement spells out that if he lies, Greenberg could then be charged with additional crimes like obstruction of justice and perjury.

In other words, Greenberg is fully locked in to telling the truth, the whole truth and nothing but the truth because he lies at his own peril. Prosecutors will use these features of Greenberg’s plea agreement to argue that it is now in his best interest to tell the truth about the crimes of others because if he doesn’t, he’s sunk.

This begs the question: Who are the “others” Greenberg can implicate? Notwithstanding the length of the plea agreement, it contains precious few clues about the identity of those who might now be at risk of indictment based on Greenberg’s cooperation.

One clear indication that other individuals are now in the fed’s crosshairs for offenses involving sexual conduct with a minor appears on page 30: “Greenberg also introduced the Minor to other adult men, who engaged in commercial sex acts with the Minor in the Middle District of Florida.” Although the plea agreement does not identify those other “adult men,” The Daily Beast previously reported that Greenberg, while seeking a pardon, wrote a letter in which he identified Gaetz as having participated in sexual acts with a minor. (Note that MSNBC has not obtained or seen the letter and has not been able to verify its contents, and Gaetz has not been charged with a crime and has repeatedly denied the allegations and any accusations of wrongdoing.)

This begs the question: Who are the “others” Greenberg can implicate?

The Daily Beast also pointed to photos of Greenberg palling around with convicted-and-pardoned felon Roger Stone. Suffice it to say, whatever evidence Greenberg has about Stone's activities is evidence that May now be fully in the possession of federal prosecutors. Stone may have won the prosecutorial battle by virtue of then-President Donald Trump pardoning him after a jury convicted him, but Stone may still see the inside of a federal prison depending on what Greenberg may have brought to the table. Nice to see that prosecutors are leaving no "Stone" unturned in their quest for justice.

Finally, one of the charges to which Greenberg pleaded guilty has garnered less attention than the others: conspiracy to commit an offense against the United States. Although the plea/cooperation agreement does not set out what crime or crimes against the United States Greenberg conspired to commit, there is one important thing we can glean from this charge: He was involved with one or more individuals to commit a crime against the U.S.

A “conspiracy” involves two or more people agreeing to commit a crime and then taking one step, called an “overt act,” toward the commission of the crime. Greenberg’s conspiracy guilty plea signals that there are co-conspirators who may also be indicted now that one of their fellow conspirators has pleaded guilty and is cooperating with prosecutors. In this way, Greenberg represents a significant falling domino that may prove to be significant to the chain reaction sure to follow.