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Donald Trump’s Latest Lawsuit Looks Destined to Fail Bigly

Donald Trump
Donald Trump speaking with supporters at a campaign rally at the South Point Arena in Las Vegas, Nevada. Image Credit: Gage Skidmore.

If nothing else, Donald Trump is consistent. Throughout the mogul-turned-politician’s career, Trump has regularly hit back against those who oppose him or in Trump’s view, sleight him; Trump has demonstrated concretely that he prefers the “offensive,” rather than the “defensive.” The result has been one of the most belligerent and caustic figures in American history. On Wednesday, Trump once again demonstrated his reluctance to play defense – instead, lashing out. On Wednesday, the former president filed a suit against New York’s Attorney General Letitia James – who recently filed suit against the Trump Organization.

The New York Times called Trump’s newest suit “a tirade” filed against “one of his chief antagonists.” And apparently, the suit was “hotly opposed by several of [Trump’s] longstanding legal advisers, who attempted an intervention hours before it was submitted to a court.”

The intervention failed. The suit was filed.

Individuals with knowledge of the suit report that the members of Trumpworld who opposed the suit did so because the suit was “frivolous and would fail.” The member of Trumpworld most opposed to the suits’ filing was the general counsel of Trump’s real estate business, who warned that filing the suit may amount to “committing malpractice.”

The suit alleges that Letitia James trespassed against Trump’s right to privacy in Florida, where the former president lives. Accordingly, the civil case James filed against Donald Trump and the Trump Organization should be dismissed.

Trump announced the filing of the suit on his social media network, Truth Social. He also took a moment to critique James, stating that “while James does nothing to protect New York against these violent crimes and criminals, she attacks great and upstanding businesses.” Trump’s statement is a stock refutation, light on specifics, as is his norm, that hits pretty consistently with GOP messaging for the upcoming midterms: Democrats are soft on crime and bad for business.

The source of Trump’s ire is that lawsuit James filed in September. James’s lawsuit was the result of a three-year investigation into the Trump Organization. James accused Donald Trump of overvaluing its assets by billions of dollars, which constituted “staggering” fraud. The lawsuit aimed to prevent Trump, Don Jr., Eric, or Ivanka from ever running a business in the state of New York while simultaneously shutting down some of the Trump Organization’s New York properties.

Trump has already attempted, without success, to stop James’s lawsuit; he filed a complaint in New York that was dismissed. The new lawsuit, filed Wednesday, revives those previous efforts; the new lawsuit, which extends for 41-pages, was filed in Palm Beach, Florida, by attorneys at a St. Petersburg-based law firm.

According to the New York Times, the new lawsuit reads like something Trump had a lot of influence over. For example, one passage reads: “As a private company, nobody knew very much about the great business that then-businessman Donald Trump had built, but now it is being revealed by James and much to her chagrin…the continuing witch hunt that has haunted and targeted Donald Trump since he came down the ‘golden escalator’ at Trump Tower in June of 2015 continues.”

I don’t much care for Trump, although I’m willing to give him the benefit of the doubt. And I generally agree that the mainstream press has treated him poorly. But Trump’s new lawsuit doesn’t appear especially sharp, or as Gerald Greenberg, a partner at a Florida law firm, put it: “this, certainly on its face, appears to be objectively frivolous. I’m aware of no authority that allows a state court in Florida to enjoin or otherwise interfere with a law enforcement investigation being conducted by New York state authorities.”

If the new lawsuit is as frivolous as some claim, it may suggest Trumpworld has been reduced to using “desperate measures.”

Harrison Kass is the Senior Editor at 19FortyFive. An attorney, pilot, guitarist, and minor pro hockey player, he joined the US Air Force as a Pilot Trainee but was medically discharged. Harrison holds a BA from Lake Forest College, a JD from the University of Oregon, and an MA from New York University. He lives in Oregon and listens to Dokken. 

Written By

Harrison Kass is a Senior Defense Editor at 19FortyFive. An attorney, pilot, guitarist, and minor pro hockey player, he joined the US Air Force as a Pilot Trainee but was medically discharged. Harrison has degrees from Lake Forest College, the University of Oregon School of Law, and New York University’s Graduate School of Arts & Sciences. He lives in Oregon and regularly listens to Dokken.



  1. el gato

    November 5, 2022 at 9:31 am

    James is another worthless politician who in craving power and notoriety, is on a fishing expedition, hoping to find something to stick on Trump so she can achieve some political bona-fides, instead of concentration on actual crime, like murders, assaults, drug dealing and thefts that are running rampant in her state. Too many innocent people are dieing in New York due to Democrats inept and worthless handling of criminals. Do some real work James, instead of salivating for craven glory on your citizens backs and bucks

  2. Terry N

    November 5, 2022 at 10:43 am

    The last comment I just read I thought came from a Faux Noise commentator or a crap house lawyer. Prosecutors don’t bring cases unless they have a reasonable chance of success. Since real judges, not crap house lawyers, have refused to stop this case, I suspect he will stand to lose big here. A fishing expedition it is not. If what he did was legal I’m going to claim my $350k house is worth ten times the amount so I can borrow more than it is worth. Come tax time I’m going to claim it is the size of an outhouse and negligee worth to reduce my tax liability. After all, if an ex-president can get away with his many crimes the rest of us should as well.

  3. El Gato

    November 5, 2022 at 1:01 pm

    James is not a city or county prosecutor, where it matters to have a reasonable chance of success. She’s a state attorney general, which is a way more political post than the others, plus she has a history of filing these cases against Trump with little to no evidence. So far she has no successes with them. If she had, it would be her, and not Hochul running for governor. Besides the fact Cuomo was a scumbag, She also went after him to get his job. That’s the nature of politics in NY.

  4. Rick

    November 5, 2022 at 11:14 pm

    A fat guy with a suit three sizes too big and a chia pet combover makes him look like a circus clown. All the frivolous lawsuits he has filed will cost him the defendants legal fees. Keep up the good work, moron.

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