Donald Trump keeps losing his NDA enforcement cases. The wider legal ramifications could be huge

For decades, Donald Trump has employed the non-disclosure agreement (NDA) as his main tool for dissuading those around him from dishing about potentially embarrassing or perhaps illegal goings-on in his inner circle. For the most part, NDA signers have abided by the terms of the documents they've signed.

Increasingly, though, there appear to be widening cracks in that wall of silence. Last week an arbitrator ruled that the former president must pay former campaign worker Alva Johnson's $300,000 in attorneys fees for trying to enforce an “unenforceable” nondisclosure agreement (NDA). Trump also was ordered to pay $50,000 for the cost of the arbitration expenses of the lawsuit.

Johnson unsuccessfully had sued Trump in 2019, claiming that he kissed her on the mouth against her will during a campaign stop in August 2016. While her underlying lawsuit was dropped, Johnson challenged the enforceability of the NDA that she had signed. As the New York Times reports, this is just the latest, most expensive legal setback for Trump regarding NDAs.

"The resolution of the claim, which Mr. Trump’s campaign filed in September 2019, came less than a year after he had lost similar efforts to enforce nondisclosure agreements against Jessica Denson, a former campaign worker, and Omarosa Manigault Newman, a former White House aide and a star on 'The Apprentice,'" the newspaper writes. It also pointed out that Trump's attempts to enforce the terms of NDAs with Stephanie Winston-Wolkoff and niece Mary Trump also went down in flames.

Victor Bianchini, a retired federal magistrate from California, ruled that the NDA that Trump has compelled numerous people to sign, is unconstitutional.

In an article published Monday, MSNBC columnist Steve Benen claimed the ruling provided an "unmistakable" message.

If you are holding back on going public with potentially damaging information about Trump you probably don't need to worry, he explained. The more Trump loses these cases in court, the less incentive for his former employees to remain silent.

"At face value, this is an embarrassing — and rather expensive — legal setback for the former president and his team. But just below the surface, there’s a larger significance to this: Team Trump’s cases regarding non-disclosure agreements keep going badly," Benen wrote.