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How Much Legal Trouble Is Donald Trump Actually In?

Donald Trump CPAC
Image Credit: Michael Vadon.

New York Attorney General Letitia James’s new suit against Donald Trump has shifted the public’s ephemeral attention span away from last month’s hot Trump topic: the investigation of the classified documents. But that investigation is still underway, with Team Trump clawing for air.

I take CNN’s reportage with a grain of salt, as the company seems to operate as an organ of the Democratic Party rather than as a purveyor of objective news. That being said, CNN’s Stephen Collinson reports that the case of the classified documents “has taken a turn against the former President and towards the Justice Department in recent days, suggesting that the classic Trumpian legal strategy of delay, denial, and distraction is not working as well as usual.”

CNN and Collinson (and MSNBC, and the New York Times, and roughly the entire mainstream media ecosystem) have been advertising Trump’s downfall for years. The ongoing documents investigation offers a similar opportunity to predict the end of Donald Trump.

“In a sign of how quickly Trump’s position may be eroding in this particular drama, several Republican senators took the unusual step of criticizing his handling of the documents,” Collinson reported. “A third-party judge gave the Trump legal team until the end of next week to formally declare whether they believe his claim that the FBI planted incriminating evidence at Mar-a-Lago during a search.” 

Also, an appellate court has ruled that Trump’s team did not show evidence supporting the claim that Trump, while still president, had declassified the 100 or so documents in question. The documents were of course seized during the Mar-a-Lago raid last August. “The search, an unprecedented step against a former president,” Collinson wrote, “provoked questions over whether the DOJ had overreached given the fraught political sensitivity of the case – particularly because Trump has shown every sign that he’s preparing another run for the White House in 2024.”

Collinson writes that Trump is employing a tried and true strategy, one that “has been remarkably successful for much of his long and controversial business and political careers.” The strategy? “Trump often substitutes a legal defense for a public relations one, blasting away at institutions, government departments, courts, officials, and the media that attempt to impose accountability or call on him to justify his allegations with fact.” 

Collinson is correct in that Trump airs his grievances publicly, often at the expense of otherwise vaunted institutions. But Donald Trump does not substitute a legal defense for a public relations one – that’s not how the criminal justice system works. I’ll state the obvious here: the legal trial – and Trump’s defense – does not suspend when Trump takes a certain PR tact. The trial continues regardless of how Trump interacts with the media. The “public relations” defense is a periphery exercise, which may be relevant politically – but is not relevant legally. 

Although, Collinson concedes that Trump has not been able to import the specifics of his public relations campaign – arguments like ‘I declassified the documents simply by thinking about declassifying the documents’ – into the courtroom. 

Donald Trump 2024

Image: Creative Commons.

Trump’s “approach flounders, however, when allegations that function well as a political strategy come up against the factual threshold of a courtroom where statements must be made under penalty of perjury,” Collinson wrote. Again, Collinson seems to be conflating a trial and the associated legal strategy with a public relations strategy. The two things are entirely exclusive from one another – even if some of the information or rhetoric overlaps. 

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. Follow him on Twitter @harrison_kass.

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. Marc

    September 24, 2022 at 10:41 am

    Tell me something I don’t know….

  2. Bori

    September 24, 2022 at 12:37 pm

    Dude, if I read “How Much Legal Trouble Is Donald Trump Actually In?” I expect an answer to that question.

  3. ed

    September 24, 2022 at 12:39 pm


    Lying (I declassified) or insinuations in bad faith (they planted) are a PR strategy, that’s all.

    And not doing these things is just a Legal strategy. Totally separate.

  4. Rich

    September 24, 2022 at 7:57 pm

    2017: The walls are closing in on Trump
    2018: The walls are closing in on Trump
    2019: The walls are closing in on Trump
    2020: The walls are closing in on Trump
    2021: The walls are closing in on Trump
    2022: The walls are closing in on Trump

    The damn walls must be moving really slowly as they’ve been closing for 6 years now!

  5. Trump 20-24 years

    September 24, 2022 at 9:24 pm

    Why do the MAGA hypocrites choose to ignore Trump stealing government documents and lying about having returned them all? National security comes in second to protecting Trump, I guess. Just call it a ‘hoax’, ‘fake news’ or a ‘witch hunt’ and move on.

  6. Steven

    September 25, 2022 at 1:35 am

    The Left is terrified of Trump, but it is already over for them. The Red Wave is almost here.

  7. Rich

    September 25, 2022 at 5:34 pm

    Hmmm….The Hillary hypocrites didn’t seem to have a problem when she stored classified documents on her server then deleted 30,000 emails and wiped the server (with a cloth, LOL) in order to destroy evidence and obstruct justice. But then again she was a democrat, so of course, nothing happened. Now we get selective outrage from the left and, ironically, charges of hypocrisy. See how that works?

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