Trump's Legal Threats Backfire

The president is used to getting his way by bluster and intimidation, but the strategy that once worked for him is now working against him.

Jonathan Ernst / Reuters

Minutes after the Stormy Daniels interview on 60 Minutes, Team Trump fired off a heavy-breathing lawyer’s letter, bristling with phrases like “cease and desist” and “retract and apologize.”

This is exactly the approach by which Donald Trump inadvertently made millions for Michael Wolff. Having so spectacularly backfired the first time, why do it again? The short answer is: Team Trump knows nothing else.

Back when he was a private businessman, Trump learned how to use law as a weapon. The lesson he took from that is that if your pockets are deep enough—and your conscience dull enough—it doesn’t matter that you are wrong. The other party will go broke before you will lose.

USA Today tallied the heavy-handed Trump litigation strategy back in June 2016. Over three decades, Trump fought 3,500 lawsuits—and faced 200 mechanic’s liens—mostly arising from disputes over unpaid bills. His strategy was to contest everything, and never quit: “The Trump teams financially overpower and outlast much smaller opponents, draining their resources. Some just give up the fight, or settle for less; some have ended up in bankruptcy or out of business altogether.”

As president, however—and especially as a historically unpopular president—Trump has abruptly discovered that his old techniques no longer work. Worse: The old techniques now work against him.

The new bottom line: If you are famous enough—and disliked enough—it doesn’t matter whether you are right. The other party will become world-famous and super-wealthy before you can win.

A heavy-breathing lawyer’s letter from Team Trump does not frighten a Stormy Daniels. She can release it to The New York Times and watch it dominate the next day’s news cycle. With news domination come economic opportunities for her—and unremitting political damage for the presidency.

In private life, Trump’s reputation as a vexatious litigant enabled him to intimidate people. Someone who received a threatening lawyer’s letter from Team Trump had to consider, “Do I want to spend hundreds of thousands of dollars and years of my life dealing with this? Or should I cut my losses and surrender now?”

That seems to have been Stormy Daniels’s thinking when she settled with Trump, pre-election.

Daniels: … I didn’t even negotiate, I just quickly said yes to this v—very, you know, strict contract. And what most people will agree with me extremely low number. It’s all the proof I need. … I didn’t wanna kiss and tell and be labeled all the things that I’m being labeled now. I didn’t wanna take away from the legitimate and legal, I’d like to point out, career that I’ve worked very hard to establish. And most importantly, I did not want my family and my child exposed to all the things that she’s being exposed to right now. Because everything that I was afraid of coming out has come out anyway, and guess what? I don’t have a million dollars.

Post-election, however, things look different. Trump actually won—and Daniels’s $130,000 payoff feels to her like chump change. She wants more, and she’s perfectly positioned to get it.

Trump’s cease-and-desist letters no longer frighten. They function as virtual currency, denominated in the millions of dollars. One of those letters enriched Wolff; now it’s Daniels’s turn—and who knows next who else? Now it is Trump who cannot afford to litigate, not because of the monetary cost but because of the reputational risks. As a skeezy reality-TV star in a third marriage governed by a tight pre-nuptial agreement, Trump could shrug off those reputational risks. As president, he cannot. They show up in polls.

Trump University set the precedent: after years of stalling, an election eve settlement. Michael Wolff sent the message: Even without a settlement, it’s still lucrative to defy the president’s lawyers. Stormy Daniels is now executing the plan. Her success may embolden still others.

The heavy-breathing threats that Trump consigliere Michael Cohen formerly growled at stiffed subcontractors, cheated creditors, enraged ex-girlfriends, and abused auditionees for The Apprentice are words that now redound against the president: “Go ahead. Sue me.”