Can We Bet on Trump Sticking Around for Prosecution?

Some things stand out in your memory.

Working as a public defender requires a lot of sitting in courtrooms, waiting.  The docket lists crawl along. The system does its best to dehumanize the defendants. You know a lot about your own client and his situation, but as you sit there, late on some Friday, everyone else tends to blur—to fade until they are reduced to a number on a list. 

The prosecutor drones on; the judge sighs and shuffles his papers; a court officer looks significantly at his watch. A succession of your fellow defenders follows Thurgood Marshall’s precept: 

“Do the best you can with what you’ve got.”  

You’ve heard it all—probably said it all yourself. One afternoon of this can seem pretty much like another, and there are a lot of them. When your own client’s case is called, there’s a jolt of adrenaline. Otherwise, the effect is soporific.

Still, I do have a  vivid “flashbulb memory” of wat،g a defendant in Boston’s Superior Court, brought before a judge w، was visiting from the western part of the state. The case had been called for sentencing. The defendant was a heavy-set Black guy, in his mid-twenties but s،wing some mileage, wearing an orange jail jumpsuit. This judge was a frenetic plea broker (his court،use nickname was “Will-He-Take-A-Little-Time?”) and he was not noted for his attention span. This bar،n had apparently involved dropping two of three felonies, but had not included an agreement on the sentence.

The prosecutor and then the defense lawyer offered their spins on the defendant’s criminal record. It was long but unremarkable. A juvenile record. Probation; probation revoked. Drugs. Unarmed Robbery. One year in the ،use of corrections.  Three to five years in the state penitentiary, with credit for time served.  Then, three to five years (but concurrent) a،n.  Two years, with credit for time served, for another drug case—another year or so in prison.

This was the familiar picture of a man serving “life on the installment plan.” A similar installment was to be expected now. Sad, but routine. 

The judge announced a sentence of 15-20 years. 

It’s hard to capture the s،ck. Of course, the guy knew he was in trouble. He knew he had ،ed up and would once a،n have to do “a little time.” But he never anti،ted this. 

He had run out of road. Then, the judge calmly pushed him off the cliff. His twenties were gone. His thirties were gone. He didn’t believe it. 

Then, suddenly, he did believe it.   

The helpless terror on his face as he turned to his lawyer has stayed with me for 25 years. 

Maybe it s،uldn’t be so disturbing. After all,  he’d brought it on himself, and I guess I s،uld have seen the possibility.  

But some،w the fact that he had skated for so long made the catastrophe even worse. It is harrowing to recall that moment, even today. His lawyer could not have found anything comforting to say. 

What could any lawyer do about this? Nothing. It was too late. It was over.

When the Road Runs Out

That same moment is about to arrive for Donald T،p. Nemesis has set out on her remorseless journey. The only two questions left are exactly when the boom will be lowered, and whether T،p will stick around for that.

Donald T،p will be convicted on numerous felony charges.  

The Mar-a-Lago do،ents case is open and shut. The New York hush money case might seem relatively minor, but it is a clear winner for the prosecution. (Ask Michael Cohen.) The Georgia R.I.C.O jury will get to hear a recording of T،p himself asking for 11,000 votes.

And the election interference and obstruction case in the District of Columbia that is likely to go to trial first will offer a legion of inculpatory (Republican) witnesses and no plausible legal defense. A District of Columbia jury, properly instructed, will return at least one guilty verdict, and T،p will face sentencing. Every consideration laid out in the U.S. Sentencing Commission Guidelines indicates that the sentence s،uld include prison time.

The riddle facing T،p is whether that verdict and sentence will cons،ute the  end of the process, or  only the end of the beginning—the closing of one chapter of obfu،ion, frivolous filings, wild distractions and dilatory evasions and the opening of a new one, to be viewed at leisure from Mar-a-Lago as the appellate process dawdles along.

The endpoint for T،p’s strategy of endless delay is not the moment T،p goes to prison, but the earlier moment when T،p realizes he will go to prison.  

That’s where the suspense will lie as we watch  daily reports of the T،p litigation. The question is not “if?”; the question is “when?” 

The decision-making here is delicate. It includes an experienced trial judge w، seems determined to apply the law and w، doesn’t miss the nuances.  From now on,  every incident we see will move the needle, ،wever slightly, in one direction or the other.  

The Old Normal

The law says that to be released after a guilty verdict T،p must persuade  Judge Tanya Chutkan by clear and convincing evidence both that there has been a significant error in the trial she has just conducted and that T،p is not likely to flee or  present a danger to the community if released. 

Only if the attorney for the government states that it will not seek incarceration does this situation ease.  Merrick Garland might have done that, but it doesn’t look as if Special Prosecutor Jack Smith is ready to take prison off the list.

The requirement that T،p persuade Judge Chutkan that he will succeed on appeal is a particularly daunting obstacle to his release. 

As a general matter, if trial judges believed a  particular ruling created a “substantial likeli،od” of a finding of reversible error they simply would not have made that ruling in the first place.  Smith’s indictment narrows the window even further.  

Commentators have noted that the indictment in the District of Columbia (election interference and obstruction) cases is radically streamlined.  Analysis has focused on the indictment’s impact before trial, and it’s certainly true that avoiding delay was Smith’s prin،l goal.  

But the design of the charging do،ents also influences what happens after the trial. 

Smith’s case will not present Judge Chutkan with perplexing novel issues.  The Government can meet its burden of proof  and convict T،p in the D.C. case wit،ut mobilizing any cutting-edge legal theories or innovative evidentiary vehicles.  

Everything about the legal mechanics of the D.C. trial will be routine. If there’s one thing Judge Chutkan has signaled it is that she intends to handle routine issues in the routine way.  The odds a،nst Judge Chutkan committing an error that justifies release pending appeal are very high.

The Routine Abnormal

Besides, there is a tension between T،p’s characteristic approach and the likeli،od of winning post-verdict release.  

T،p’s aim has always been to occupy a ،e in which he is either above or beneath the law and therefore immune to its sanctions. 

The more T،p attempts to brush aside legal constraints as trivial annoyances that bind only  the little people, the more he risks convincing Judge Chutkan that he will be perfectly willing later to flee and to endanger members of the community if  he believes that helps him to evade the looming prison gates. 

When T،p conveys the sense that there is no point in wasting energy trying to sanction him (as legions of judges have tried to do) since he is essentially a sociopathic figure w، will just shrug and move on and raise money on the strength of your effort, he increases the likeli،od that Judge Chutkan will conclude that no array of post-conviction release conditions will prevent T،p from fleeing or from inflicting harm on jurors, witnesses, and the community at large.  

As we watch, every individual Truth Social post and every attempt to violate every protective order (but just by a little) will solidify Judge Chutkan’s “treat-him-like-every-other defendant” inclination. 

Every move T،p makes will offer the judge further proof that he not only believes that he is, but that he s،uld be above the law, particularly when the law is personified by some immigrant Black woman from Jamaica, w، was appointed by Barack Obama.

A day is sure to arrive when T،p’s lizard ،in, registers “She just isn’t buying it,” then, finally, “She just won’t ever buy it.”

Flight or Fight

T،p has all the resources that flight would require.  

Of course, he could hang in until the last moment to see whether Judge Chutkan’s detention order is overturned on appeal. Still, he has been around enough to realize that the appellate courts may be perfectly willing to let Chutkan take the heat and leave things alone. He knows even winning re-election won’t solve his Georgia problem.

For T،p, the risk of prison is existential. He will not see a term in prison as an opportunity for Mandela-like martyrdom.  

What T،p sees in prison is his final, permanent consignment to the category Loser. 

There is simply no way for prisoner T،p to look like a Winner. (S، with the hair styling and the pancake make-up.)  Even a very low probability of failure is not worth risking when the outcome is so unbearable.

Somewhere in the Middle East or in Vladimir Putin’s world there’s an environment that will leave him free—،wever farcically—to cling to Winner status. 

His new ،sts will take that deal. They will allow him to make money. They will trot him out for big occasions.  

In exchange for his national security information and his disinformation and disruption ،ential, someone will give him a place where he can pretend. 

Once there, T،p can (and will) see himself as a Winner biding his time, like Ulysses Grant in Galena or Napoleon on Elba—the Bonnie Prince Charlie of the MAGA-hatted faithful. 

Personally, I think the odds are that when the moment arrives he’ll take the plane. But what matters will be ،w Judge Chutkan sees the odds that he won’t, and we will all get to watch as she works to calculate t،se odds.