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Defeat in dubious civil suit adds to Trump's legal losing streak

After The New York Times exposed Trump's controversial finances, he sued the newspaper. The litigation proved to be yet another embarrassing failure.


It was nearly four years ago when The New York Times published one of the most devastating reports I’ve ever seen. In the first real breakthrough on understanding Donald Trump’s controversial finances, the newspaper exposed evidence of “outright fraud” and “dubious tax schemes” that the Republican exploited to receive hundreds of millions of dollars from his father.

The findings painted a picture in which the then-president, far from the self-made man he pretends to be, relied heavily on legally dubious family handouts. As regular readers may recall, it was the first of three brutal reports on Trump’s financial history, leaving little doubt that he had spent much of his adult life meandering between failures and fraudulent endeavors.

Eventually, he responded to the reporting by filing a $100 million lawsuit against the newspaper and its source — his niece, Mary Trump — who helped expose him as a fraud. She responded to the litigation at the time by saying, “I think he is a f------- loser.”

Her pointed choice of words came to mind yesterday as the former president’s case was thrown out of court. NBC News reported:

A New York judge dismissed Donald Trump’s 2021 lawsuit against The New York Times on Wednesday. ... In his ruling, Justice Robert R. Reed of the state Supreme Court in New York County said Trump’s claims against the Times and three of its journalists for their Pulitzer-winning series on his undisclosed finances in 2018 “fail as a matter of constitutional law.” (Supreme Court is the name of New York’s top trial court.)

As part of the Republican’s defeat, the former president was also ordered to pay the attorneys fees and legal expenses for the Times and its journalists.

His case against Mary Trump is still pending, though she and her lawyers have filed a motion to dismiss.

If recent history is any guide, her odds of success are pretty good.

Circling back to our earlier coverage, Trump has made all kinds of threats over the past several years, vowing to sue perceived foes, though the rhetoric was often hollow.

After leaving the White House, however, he’s been more willing to follow through on his legal chest-thumping. Two years ago, for example, Trump sued social media giants, accusing them of conspiring against him. The litigation was more of a stunt than a legitimate case, and it was dismissed.

Around the time that lawsuit was collapsing, the former president came up with a related idea: Trump sued Hillary Clinton and several other Democrats, alleging they tried to rig the 2016 presidential election by bringing attention to his Russia scandal. That case didn’t just fail, it led a judge to impose sanctions against Team Trump for having filed a meritless lawsuit in the first place.

Now his case against the Times has collapsed, too.

There’s no reason to assume the losing streak will end anytime soon. Trump’s absurd civil case against the Pulitzer Prize Board appears destined for failure, and the Republican probably shouldn’t get his hopes up about his lawsuit targeting Bob Woodward. Indeed, the prospect of additional court sanctions against the former president and his lawyers continues to hang overhead.

And these are just the cases in which Trump is the plaintiff. There are also pending civil cases in which he’s also the defendant — including the E. Jean Carroll case, the trial of which is ongoing — on top of his recent criminal indictment in Manhattan, and the several criminal investigations that might yet add to his legal woes.

In other words, yesterday’s news was awful for Trump, but it wasn’t his first embarrassing legal defeat, and it almost certainly won’t be his last.

This post revises our related earlier coverage.