I appreciate John’s perspective that it is a shame that the criminal case against Allen H. Weisselberg plead out and did not go to trial due to the serious public interest in the case.  My concerns are focused not so much on the fact that the case settled, which I view as inevitable given the reality of plea bargaining in our criminal legal system.  My concern is, instead, about how it settled compared to other criminal cases.

First, what was typical about this plea negotiation process?  The fact that the judge got involved is typical in state courts (but prohibited in Federal Courts).  As the NY Times recounted, the judge made it clear to the defense that he “did not think that white-collar criminals deserved to be spared prison time.  And if Mr. Weisselberg was convicted, the judge warned that he would order him into custody that same day.”  This is also typical. I have seen judges announce from the bench, in open court, that they will “max” out defendants who reject a plea deal and go to trial and are convicted. This is typical pressure that judges put on defendants in state courts to accept plea deals. The difference here is that the judge made the statement in chambers and not (it seems) directly to the defendant.

In some contexts, this might be considered reality testing as the judge was, arguably, just making sure the defendant knew what would happen if he went to trial and lost.  This plea negotiation spread out over many months.  It is hard to know how typical this is because we don’t have great data on when criminal cases plead out relative to when they are filed.  It is certainly true that serious cases often taken an extended time to settle as defense lawyers prepare their cases and have more information to share with the prosecution that can help in the plea negotiation process.

Prosecutors regularly condition plea deals on defendants “flipping” or testifying against co-defendants or people further up the chain in a criminal enterprise. This is more common in gang and organized crime cases, but can also happen in white collar cases as the Weisselberg case illustrates.

What was not typical about this plea negotiation? The defendant had high-powered well-resourced lawyers.  This may have contributed to why the judge didn’t want it to go to trial. He knew the trial would take longer than a typical case.  But it is typical that judges don’t want cases to go to trial (both criminal and civil) and will often work hard to pressure the lawyers to work out a deal.  The big thing that was not typical is the deal this defendant got and how. In the end, the prosecutors didn’t get his testimony against Trump, but just the Trump Organization. The judge agreed to undercut them and give less jail time.

This was only possible because Weisselberg was “pleading to the sheet” so his deal didn’t depend on the prosecution because he didn’t need them to agree to dismiss charges. Without knowing exactly why the prosecution wanted all fifteen charges, it does seem that this insistence is where the prosecution lost their leverage in the negotiation. Weisselberg could plead open to the judge – that is, without any agreement with the prosecutor regarding the sentence – and the judge could sentence him to whatever the judge thinks is appropriate.

Mr. Weisselberg was charged with fifteen felonies. He did not agree to cooperate in any meaningful way with the prosecution.  In the end, he will serve 5 months or less in jail (likely far less), and pay $2 million in taxes.  This is assuming there is no trial in the Trump Organization case and/or that he testifies well enough to be seen by Judge Merchan as being “fully truthful.” I don’t think it is a stretch to assume that Mr. Weissleberg knows what the Trump Organization defense is and even how likely it is that the case will go to trial. It is rare for human defendants to go to trial and it is even more rare for corporate defendants to go to trial in criminal cases. In reality, a promise to testify truthfully is unlikely to mean much of anything if there is no trial and no testimony is needed.

I don’t agree with the extreme prison sentences that are routine for first time offenders in the United States. But this case highlights the inequalities.  On far less serious cases a typical defendant, including first time offenders, may spend more than 5 months detained in county jail just awaiting trial. During COVID, courts became backlogged and many defendants languished in custody for months and months just waiting for plea offers.

Although Judge Merchan took a hard line in not agreeing to a no-jail sentence, he also, in the end, agreed to undercut the prosecution offer.  This is not typical. This speaks of Weisselberg’s privilege and the reality that the wealthy in this country experience a different criminal legal system.