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Is Donald Trump Legally Doomed?

President of the United States Donald Trump speaking with attendees at the 2019 Student Action Summit hosted by Turning Point USA at the Palm Beach County Convention Center in West Palm Beach, Florida. Image by Gage Skidmore.
President of the United States Donald Trump speaking with attendees at the 2019 Student Action Summit hosted by Turning Point USA at the Palm Beach County Convention Center in West Palm Beach, Florida. Image by Gage Skidmore.

How much legal trouble is former President Donald Trump in? That is often a difficult question to answer. Even for a dedicated news consumer, it can be hard to keep straight exactly who is suing Trump (or one of his accomplices) and on what charges. There are just so many suits and/or investigations involving Trump.

Case and point, the New York Times dropped this headline yesterday: “Where 6 Investigations into Donald Trump Stand.” 

A Growing Docket of Investigations

Many political observers, myself included, at some point began tuning out legal news regarding Trump or his family or his cronies. The endless flood of hyperbole involving Paul Manafort or Eric Trump or Jared Kushner or Trump’s business or Trump’s presidency – it all just started to bleed together, somewhere early in Trump’s first term. But now a new suit against Trump has cut through the din, standing apart, appearing significant.

‘He’s done’: how Donald Trump’s legal woes have just gotten a lot worse, a Guardian headline read today.

Donald Trump’s legal perils have become insurmountable and could snuff out the former U.S. president’s hopes of an election-winning comeback, according to political analysts and legal experts,” David Smith reported for The Guardian. The reason? “On Wednesday, Trump and three of his adult children were accused of lying to tax collectors, lenders and insurers in a “staggering” fraud scheme that routinely misstated the value of his properties to enrich themselves.”

New York’s Attorney General Letitia James filed the suit that seeks at least $250 million in damages. In addition to money damages, James’s suit is seeking to ban Trump, Donald Trump Jr., Eric Trump, or Ivanka Trump from ever serving as an officer of a business in the state of New York. And, the suit is seeking to ban any Trump company from ever doing business in New York state ever again. 

“James said Trump massively overstated the values of his assets in statements to banks, insurance companies and the IRS to obtain more favorable loan and insurance terms for his company, as well as lower its tax obligations,” CNBC reported.

“Trump falsely inflated his net worth by billions of dollars,” James said at a press conference. “For too long, powerful, wealthy people in this country have operated as if the rules do not apply to them. Donald Trump stands out as among the most egregious examples of this misconduct. With the help of his children and senior executives at the Trump Organization, Donald Trump falsely inflated his net worth by billions of dollars to unjustly enrich himself and cheat the system.”   

James filed a 220-page civil lawsuit in Manhattan Supreme Court. The suit alleges that “the number of grossly inflated asset values is staggering, affecting most of not all of the real estate holdings in any given year. All told, Mr. Trump, the Trump Organization , and the other Defendants, as part of a repeated pattern and common scheme, derived more than 200 false and misleading valuations of assets included in the 11 Statements covering 2011 through 2021.” 

Examples of Trump’s fraudulent behavior abound; for instance, Trump placed the value of his Mar-a-Lago property at $739 million, claiming that the resort sat on unrestricted property that could be developed. In reality, the property was subject to myriad restrictions and generated under $25 million per year; Mar-a-Lago should have been valued at roughly $75 million – about one-tenth of what Trump actually listed. 

Another example is Trump’s Wall Street property. Outside banks appraised the property at $200 million and $220 million in 2010 and 2012 respectively. But in Trump’s 2011 and 2012 Statement of Financial Condition, he listed the property at $524 million and $527 million respectively. 

Trump responded harshly to the suit. “Another Witch Hunt by a racist Attorney General, Letitia James,” the former president wrote on his Truth Social account. “I never thought this case would be brought – until I saw her really bad poll numbers. She is a fraud who campaign on a ‘get Trump’ platform, despite the fact that the city is one of the crime and murder disaters of the world under her watch!”

Trump has certainly been subject to overzealous prosecution, both legal and political. And he’s correct that there is political incentive to take him down; Trump is the Democrats’ White Whale. But something about tax fraud feels more plausible and harmful – less petulant – than a classified documents raid, or an in-depth examination of the tweets Trump sent on January 6th. These new charges speak to the inconsistencies between Trump’s marketed self and actual self, threatening the working-class-hero image Trump has constructed, threatening to expose him for what he is: an enemy of the working class.

But let’s wait and see if these charges are more legitimate than the Russiagate or Liz Cheney stuff.  

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. KR

    September 22, 2022 at 9:21 pm

    I know what you are saying Harrison, but there sure are a lot of videos out there of that DA stating how she is going to get Trump. Even if she does get Trump on something, I see him pushing this through the courts until he gets a outcome that suits him.

    But like you said, we’ll see.

  2. Steven

    September 22, 2022 at 9:23 pm

    The left is about to be defeated and they know it. Russia is going down, China’s next. Trump will run, he will win, we will take the government back and the deep state (the left) will be purged, starting with the FBI.

  3. Dr. Scooter Van Neuter

    September 22, 2022 at 10:29 pm

    Nothing currently Trump’s charged with would legally preclude him from running, but he’s so (wrongly or rightfully) tainted at this point, he’ll never be able to effectively govern.
    It’s DeSantis time.

  4. xheavy

    September 22, 2022 at 10:36 pm

    It does not matter anymore.

    Its evident that there is a whole pantheon of enemies who would secretly fantasize about killing Trump outright so they can continue the current demonic extreme left rule and destruction of America.

    If Trump was sworn in 2016 and a week later started mumbling, kissing children, sniffing little girls, having a son who engaged in Chinese money and all sorts of deviant crap etc he would have been handcuffed and hauled out of the oval office on a unaminous voice vote from congress. Poof gone. This is Biden currently in office. Considered absent in the mind because hes gotten too damn old. And they dont care.

    Just never have someone like Trump who can actually consider the various problems as President and try to fix it. The people love him.

    Im pretty sure the 81 million Imaginary Voters keep Biden’s thoughts warm and cozy at night. Key word. Imaginary.

    Would I vote for Trump? No. Im not that stupid. Not in the age of where you publicly do something and get on some list somewhere as a enemy of the far left. Politics have become weaponized.

    In due time all of that mess will be cleaned up and we will either have a chance to fix America top to bottom or lose it all. I am leaning towards losing it all as a Country. Smothered in glowing radioactive ash. Serves us right.

  5. Ryan Scriver

    September 22, 2022 at 10:58 pm

    Donnie the Rust Stain has more Russian DNA in him than his wife, Melania the Pro from sucking up Putin so much. He should be tried as an enemy of the State and punished accordingly.

  6. GhostTomahawk

    September 23, 2022 at 1:38 am

    All of the lawsuits from NY will be tossed in court. As a prosecutor you lose ALL credibility when there is video evidence of political bias. You can’t have years of video telling people it’s your mission and then expect a court of law to believe you didn’t violate laws to build your case… if you have one. With all that’s going on in NY they are choosing THIS to spend millions on. Lol

    If there were real criminal cases…. They’d already be under way.

    Sorry clown. Yet again your wet dreams aren’t reality. All of these “cases” are political bluster essentially wasting tax payer money to smear their political rival. If you don’t know that… you’re as retarded as I say you are.

    Either way… scoreboard

  7. Bobby

    September 23, 2022 at 12:21 pm


    You don’t know what you’re talking about, but I’m fairly certain that won’t stop alternate reality trip.

  8. Duh

    September 23, 2022 at 1:19 pm

    Author claims to have tuned out the corruption and labels it hyperbole? Really bright.

  9. Tomb

    September 24, 2022 at 10:52 am

    Lets stop the insults.

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