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Rejoice, America: These Trials Should Bring Donald Trump to Ruin

This is the week that the former president’s epic legal misadventures begin. It’s hard to imagine his coming out unscathed.

Andrew Kelly/Getty Images

So, here’s a preview of coming attractions. Trump: The Lawsuits debuts this week. Monday, in fact, in the Manhattan civil courtroom of Judge Arthur Engoron, judge of the Supreme Court 1st Judicial District in New York. This is the first of seven—count ’em, seven—trials Donald Trump is scheduled to face between now and Election Day. Let’s take stock of all the litigation to come.

Liberals are wired to see disaster in everything. We’re not supposed to discuss matters like this in the tone I’m about to use. But I submit that in this case, a little optimism is warranted, because I think it’s quite possible that by next November 5, Trump could not only be a damaged candidate because of these cases, but his careers (political and business), and indeed his life, could be in tatters.

Let’s start with this week’s case. New York Attorney General Letitia James has charged that Trump and his family repeatedly inflated the value of their properties from 2014 to 2021. Perhaps most flagrantly—and certainly most vainly and grossly from the perspective of insecure phallic metaphor—he used to brag that his apartment in Trump Tower was nearly 30,000 square feet. That is to say: three times its actual size. James seeks $250 million in penalties.

Last Tuesday, Judge Engoron issued an excoriating ruling against Trump, agreeing with James that Trump did what she says he did. He stripped the Trump Organization of several of its New York business certificates. He also ordered each of Trump’s attorneys to pay a $7,500 sanction fee to the court—and while that is not a lot of money, it is an almost unheard-of step.

Now Engoron presides over the trial. And since he, not a jury, will decide things, a bad outcome for the former president seems almost baked into the cake—unless somehow Trump’s legal team comes up with a wholly new, and noncrazy, defense. There’s a reasonable chance that Trump will be ordered to fork over something close to the $250 million James seeks. He can afford it (or so he says), and of course he’ll appeal. But he’ll have been forced to drink a humiliating cup of truth over a scam he’s been pulling for years. There will be weeks of headlines about how he might lose Trump Tower. Swing voters will notice, and not sympathetically.

So that’s the first case. Case number two starts later this month in Atlanta. There was a major development here last week when one of the defendants, Scott Hall, pleaded guilty. He has agreed to testify about some dubious-looking electoral mischief in Coffee County, where the former head of the elections division and the former county GOP chair are alleged to have given Trump associates voter data. Whether any of that reached up to Trump himself—I guess we’ll find out.

In Fulton County, two of Trump’s 18 co-defendants in the Georgia voter fraud case will go on trial October 23. Prosecutors in Georgia estimate this trial will last about four months and include 150 witnesses. That will extend into the primary season. These trials will be in front of juries, so maybe Trump’s jury will include a MAGA-head nullifier. But the fact that we have Trump on tape telling Brad Raffensperger to go find him enough votes to change the result would seem to make this one pretty open-and-shut too.

Skip ahead to next January 15—and think about the lovely timing of these: spread out over the primary season, with even perhaps more than one proceeding going on at once—when E. Jean Carroll’s civil defamation suit is supposed to start. This one too looks grim for Le Grand Orange. Back in early September, a New York federal judge ruled that Carroll will not have to prove a second time that Trump defamed her. The case, the judge said, is only about the extent of the damages Trump will have to pay. So, in essence, he’s already lost that one, just as he has seemingly in essence already lost this week’s civil case; the only outstanding question is how humiliating the finding will be.

Case number four is a juicy one, and it has received the least attention so far of the septet. This is a class-action suit accusing Trump and children of fraud by convincing customers to invest in get-rich-quick schemes while accepting “large, secret payments” from the companies they were pitching. One plaintiff, a hospice caregiver in California, paid $499 to register for a course and says she spent thousands attending seminars to earn a whopping $38. This is the kind of matter Trump has a history of settling—remember, he paid $25 million to avoid facing the music over Trump University. But if this one goes to trial, imagine the stories we’ll hear. Here’s hoping the plaintiffs refuse to settle so that the voting public can hear every detail of what cheap, sleazy people these are.

Number five, set for March 4, is the Big Kahuna: the January 6 insurrection trial, before Judge Tanya Chutkan in Washington, D.C. Trump unsuccessfully sought a two-year delay on this one. There are reportedly up to 250 potential witnesses in this case, and a prosecutor, Jack Smith, who clearly means business. This is the one where any number of big fish could flip on Trump. (Why do you think he held that fundraiser for Rudy Giuliani?)

Again, while one should never be too confident about guessing a trial’s outcome, we already have a lot of evidence telling us that Trump was loving the violence of that day and wanted his own vice president to hang. Yes, there’s that line from his speech urging people to be peaceful. But there’s plenty of evidence that contradicts the idea that he harbored anything but ill intent.

The sixth case, which is scheduled to start the same month as the insurrection case, on March 25, is the Stormy Daniels hush-money case. Now, this matter is generally considered the weakest of the group because a payment like the one Trump allegedly made isn’t a felony unless there’s an underlying felony crime. Manhattan District Attorney Alvin Bragg has laid out a rationale along those lines, having to do with violation of campaign finance laws. It looks pretty straightforward to me, but as The New Republic’s Matt Ford explained, Bragg has done some creative legal embroidery to get this case to trial. He’ll have to convince a jury, in essence, that Trump paid Daniels off for the specific purpose of influencing the election. That he did so seems obvious common sense to you and me; I mean, why else would he have paid her? But common sense doesn’t always win in a courtroom, where statutes reign supreme. Still, in a jurisdiction where the defendant isn’t exactly beloved, there seems a chance that common sense can actually defeat obscurantist legal language.

Finally, the seventh case is the classified documents case, set for late next May. That case will be heard in a Trump-friendly jurisdiction before a judge he appointed to the bench. On those two points, Trump has lucked out. However, the voluminous evidence against him, in the form of photos of boxes of classified documents, along with that tape of Trump admitting that he lacks the power as an ex-president to declassify documents, is rather less fortunate.

Trump will be playing the role of semi-professional defendant throughout the primary season and in the run-up to the GOP convention, scheduled for July 15 in Milwaukee. Is it that hard to imagine that Republican delegates may end up convening to nominate a candidate who has just been dealt one, or two, or three convictions? Trump is additionally at risk of having to pay up to three staggeringly expensive financial penalties—in the current case, the Carroll suit, and the class-action suit. I find these scenarios very easy to imagine. In fact, I daresay that some crime-and-punishment cocktail along those lines seems more likely to be served than not.

If I’m right, here’s what will happen. He’ll scream, his people will turn violent, and it will all be ugly and painful and difficult to live through. But one thing that probably won’t happen? His return to the White House. This is why I’ve always said that come January 2025, there are not just two, but three, places Donald Trump might be living: the White House; Mar-a-Lago; or a dacha on the Black Sea, 30,000 square feet, easily the biggest and most beautiful dacha anybody’s ever seen. Or, of course, a federal prison cell. In a suit to match his face.