Donald Trump’s ultimate no-win scenario just came home to roost

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When New York Attorney General Letitia James forced Donald Trump to sit down for a deposition earlier this year in her civil fraud case, Trump invoked the Fifth Amendment hundreds of times. This led a number of defeatists on our side to say “oh no, he’s getting away with it all.” But I remember saying at the time that Trump had just forfeited the case and would definitely lose.

Sure enough, this week the judge in the case issued a summary judgment that Trump indeed committed wide scale financial fraud. You know you’re on the wrong end of things when the judge hands down the ruling before the trial even begins. No doubt one of the reasons the judge went this route is that when Trump was given the opportunity to defend his business practices, he instead pleaded the fifth over and over. He was, as I said, forfeiting.

There’s this popular notion that pleading the fifth somehow gets you off the hook. But that’s not how it works at all. If anything it’s the opposite. When you plead the fifth in something like a civil probe or a congressional hearing, you’re essentially putting a big red flashing neon sign over your head that says “Criminally investigate me for the specific thing that I just refused to speak about.” Or alternately, you’re saying “I’m already under criminal investigation for the thing I just refused to speak about, which is why I’m afraid of saying anything about it.”

It’s a nightmare scenario when you’re under civil investigation and criminal investigation at the same time. When you’re forced to testify in the civil probe, you’re afraid to say anything at all, for fear you’ll end up handing criminal prosecutors something they can use against you. So you plead the fifth in the civil probe. But by refusing to speak up and defend yourself in the civil probe, you’re essentially telling the courts that they can go ahead and side with the other party. We’re now seeing that, with Trump’s decision to plead the fifth across the board in his civil deposition leading directly to the summary judgment against him.

Donald Trump is listed as a witness in next week’s accompanying civil trial to determine the size of the financial penalties. This means Trump will once again have the opportunity to defend himself. But if he does, criminal prosecutors like Jack Smith and Fani Willis will be listening closely to see if he says anything they can use against him. On the other hand, if Trump once again simply pleads the fifth in this civil trial, he’ll essentially be giving the judge the greenlight to hand out all the financial penalties that Letitia James is seeking. It’s the ultimate no-win situation.

So when Donald Trump pleaded the fifth hundreds of times in the Letitia James case earlier this year, he wasn’t “getting away” with anything. He was forfeiting the case. Whether he fully understood it or not (any competent lawyer would have explained it to him), he was forfeiting his entire financial holdings, out of the fear that speaking up and defending himself might make it easier for prosecutors to put him in prison. The kicker is that Trump is losing all his money and he’s still going to end up in prison.

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