The True Size of Donald Trump’s Losses Exposed: An In-Depth Analysis of His Downfalls and Failures

September 5, 2025

In his weekly newsletter, Elie Mystal parses everything from Trump’s recent spate of legal losses to Tom Cruise’s running prowess.

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Donald Trump speaks at a press briefing in the Oval Office.

(MANDEL NGAN / AFP via Getty Images)

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The Trump administration repeatedly lost in court this week. A federal judge in California ruled that Trump violated the Posse Comitatus Act when he deployed federal troops to Los Angeles. A federal judge in Massachusetts ruled that Trump violated the law when he attempted to cut off federal funding to Harvard. The Court of Appeals for the Federal Circuit ruled that most of Trump’s tariffs are illegal. And a panel of judges from the Fifth Circuit Court of Appeals—the most conservative and reactionary appellate court in the country—ruled that Trump’s targeting of Venezuelans was an illegal use of the Alien Enemies Act.

That’s a lot of losses. Donald Trump continues to be the losingest president, in court, in American history. He is the biggest loser.

In a normal country, this string of rebukes from courts of law would dominate the news cycle. Editorials and think pieces would abound about why the president can’t seem to follow the law. People would question why the tyrant at the head of the government can’t put two executive sentences together that don’t obviously violate some kind of statutory or constitutional principle.

In our country, nobody really cares, and we all know why. None of these losses are final. Every single one of these cases will be appealed to the Supreme Court, and we all expect the Supreme Court to reverse these decisions to further the president’s MAGA agenda. Trump also expects that. He’s not even pretending to be chastened by his losses. He’s not firing his lawyers and demanding better service. He’s going to go to the Supreme Court and expecting them to do his bidding, which they almost certainly will.

The president lost four court cases in a week, and none of it matters. That is the evidence that we’re living in an autocratic dystopia.

The Bad and the Ugly

Current Issue

• In Trump’s one court win this week, a panel of MAGA judges on the DC Court of Appeals ruled that the president is allowed to rescind $20 billion in environmental funding. The fact that Republicans continue to be allowed to pillage and poison this planet has become my go-to data point to support the proposition that God is dead.
• Trump is going to ask the Supreme Court to throw out the $5 million verdict E. Jean Carroll won against him. Normally, the court wouldn’t weigh in on such a matter, but given that the Republican justices are just there to give Trump what he wants, he knows it’s worth a shot.
• Politico published an almost farcical excuse for “journalism” this week in the form of an article titled “Chief Justice John Roberts is wary of entering the political fray, his chief political adviser says.” The outlet later changed the title to “…his top adviser says.” But the first version was better because it made the mistake of telling the truth.
• The Supreme Court’s approval rating remains at near-historic lows, so maybe Politico needs to do more sanewashing of the Roberts political agenda.
• In some happy news, Cardi B won again. She was found “not liable” in a $24 million assault claim that was brought against her by a security guard who made one of the most bogus claims I’ve ever heard. Cardi B is undefeated in court, and I don’t know why fools keep testing her. She is the opposite of Trump. She will dog walk you.

Inspired Takes

• This is a really thoughtful piece by The Nation’s Katrina Vanden Heuval about the dangers of trying to out-Trump Trump in the name-calling game. The most important part of her argument, to me, is that if you’re going to talk the talk, you also have to walk the walk. Trump doesn’t just engage in schoolyard insults while desperately seeking the attention his father never gave him (see what I did there). He also takes bold (illegal, unconstitutional, immoral) actions to back up his online bluster. That’s the part that many Democrats who seem eager to get into the insult-comedy business seem to lack. You can’t talk like a dominating dog online and then govern like a scaredy cat.
• Sometimes I dread reading Gregg Gonsalves in The Nation because he reminds me that the people in charge of public health in this country are psychopaths who will kill us all. But, anyway, his latest piece is about how RFK Jr. is a psychopath who will kill us all.
• In her new book, Amy Coney Barrett positions herself as a helpless cog in a legal machine that gives her no choice but to rule the way she does, even if she doesn’t like it. As Joe Patrice explains over at Above the Law, her entire act is risible. But it’s an act we’ve seen from every first-year, fascist-curious law student who wants to make a career as a Federalist Society judge.

Worst Argument of the Week

Trump’s latest attempt to institute martial law involves his threat to use non-federalized National Guard troops to police cities in blue states where Black people and Latinos live. His current focus is Chicago. According to Governor J.B. Pritzker, he has threatened to send troops from Texas but not said he will call them up under his personal control.

While this would avoid Trump’s various problems with the Posse Comitatus Act, it would create a new problem. Namely: starting a civil war.

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Trump claims he has authority to call up non-federalized troops to support his policy directives, provided states volunteer the forces. That might be true, but it’s complicated. (Georgetown law professor Steve Vladek does an excellent job of parsing Trump’s questionable legal authority to do this.) Even if he does have the authority to request the troops, he doesn’t have the authority to direct them to another state to conduct law enforcement in that state. He can’t just say, “Will no one rid me of this turbulent state?” and let Texas figure out what to do from there. Sending troops from one state to another over the other state’s objection is an act of war. Trump is essentially threatening to let Texas invade Illinois if Texas Governor Greg Abbott feels like it.

I hate to bring this up because I’m not Neil Gorsuch, but one state’s invading another state would have been anathema to the people who wrote the Constitution. The whole point of our federalized system, our confederacy of states, is that each state has broad authority to police itself. Indeed, the Constitution explicitly reserves the “police power” of the government to the states. There are only rare cases when the federal government is allowed to usurp that power from the states (and all of them involve foreign invasion), and there is literally no case when one state’s troops are just allowed to show up, uninvited, in another state, and do anything. Texas sending troops to Illinois to get rid of all the immigrants would be the equivalent of New York sending troops to New Jersey to get rid of all the Phillies fans.

Should Texas invade, Illinois would have a couple of legal options. It could sue the Trump administration for its abuse of the National Guard’s power. Or it could sue Texas directly for, you know, invading its sovereign territory. The latter kind of lawsuit would be heard directly by the Supreme Court, because lawsuits between states are among the ones where the court has “original jurisdiction,” meaning that such disputes start and end at the Supreme Court.

Of course, another option would be for Illinois to fight. Pritzker could raise his own National Guard troops, and citizens of Illinois could be enlisted to fight the invaders from Texas.

But… you can see where that leads us. Civil wars start when people are compelled to defend their homes from outsiders who have no right to be there.

I don’t know how many Texans Gregg Abbott is willing to send to Chicago to die so that some guy fleeing persecution gets deported from a parking lot at Home Depot. But if this keeps up, we’re going to get an answer to that question.

What I Wrote

The Nation’s Sasha Abramsky asked me “how is it legal?” for Trump to use military lawyers as immigration judges. I said something to the effect of: “It’s not, but the whole [expletive] system is [expletive] broken and we haven’t fixed that for [expletive] reasons.” Then I wrote about it, without the expletives.

In News Unrelated to the Current Chaos

Vikram Murthi wrote a truly brilliant article in The Nation exploring Tom Cruise’s physicality and how his commitment to doing all his own stunts, even in this era of computer-generated special effects, makes him essentially “the last action hero.” Whatever you think about Cruise as a media amalgam or religious weirdo, Murthi’s point is, I believe, undeniable.

But there’s one aspect of Cruise’s on-screen physical talents Murthi glossed over: Tom Cruise’s running. I watch Cruise’s movies just waiting to see him run. It is perfect. Tom Cruise is the actor greatest at running in cinema history.

If you watch enough sports, and watch enough movies, you will quickly realize that most actors have no idea how to run. Athletes know how to run; actors can’t even pretend to. There is no actor in all of the Jurassic Park movies who has credibly run away from a dinosaur. There is no actor in any superhero movie who has credibly run at superhuman speeds. Ezra Miller, who plays the freaking Flash in DC movies, functionally has no idea how to run fast (he’s also, by all accounts, a punk). He could be replaced by any Olympic sprinter and all his movies would look better.

Tom Cruise puts most of these other actors to shame. If you Google “Tom Cruise running,” you will find that there’s basically a cottage industry devoted to dissecting his run, imitating it, and figuring out how he’s learned to do it so well. It’s a deep rabbit hole.

My belief is that Cruise’s secret is not in his body but in his face. Running is a desperate act. People over the age of 15 run as fast as they can only when they’re under incredible duress.

They’re chasing something, or being chased, and the penalty for failure is such that people push their bodies to their maximum physical speed. Nobody is casually running as fast as they can. Something has happened, usually something very bad, to push them to this limit.

With Cruise, you can see on his face the bad thing that is happening. “The bomb is on the plane! If I don’t get there as quickly as humanly possible, we’re all dead!” Just go back and watch The Firm. Cruise spends most of the movie in a suit and tie and carrying a briefcase; when he takes off and runs out of his law firm with his briefcase, you believe that he is literally running for his life. He’s so committed to the bit that your mind naturally asks, “Why won’t he get rid of the briefcase? It’s slowing him down!” Then, later in the movie, you learn what’s in the briefcase and it all comes together.

There are other great running actors. Sylvester Stallone’s most famous scene in his long-ass career is, still, running up the steps of the Philadelphia Museum of Art. Will Smith is also great at running, much better than he is at slapping. Jennifer Garner put in serious running work in Alias.

But none of these actors can match Cruise. Maybe everybody else is just weighed down by bad Thetans?

Elie Mystal

Elie Mystal is The Nation’s justice correspondent and a columnist. He is also an Alfred Knobler Fellow at the Type Media Center. He is the author of two books: the New York Times bestseller Allow Me to Retort: A Black Guy’s Guide to the Constitution and Bad Law: Ten Popular Laws That Are Ruining America, both published by The New Press. You can subscribe to his Nation newsletter “Elie v. U.S.” here.

How did the New York fraud ruling impact banks and lenders who relied on Trump’s inflated valuations?

Trump’s Business Failures: A Pattern of Bankruptcy and Debt

Donald Trump’s public persona frequently enough projects success,but a closer examination reveals a history punctuated by significant financial setbacks.These aren’t isolated incidents; they represent a recurring pattern of overleveraging, poor business decisions, and ultimately, failure. Understanding these Trump business failures requires looking beyond the branding and into the documented financial realities.

Six Bankruptcies: Trump-related businesses have filed for bankruptcy six times between 1991 and 2024. These filings weren’t simply strategic maneuvers; they were frequently enough the result of unsustainable debt loads and declining revenues.

Casino Empire Collapse: The Trump Casino Associates bankruptcy in 2004, and the subsequent failures of Trump Hotels & Casino Resorts, highlight the disastrous performance of his atlantic City ventures.Competition from other casinos,coupled with poor management,led to massive losses.

Trump University Lawsuits: The highly publicized lawsuits surrounding Trump University, ultimately resulting in a $25 million settlement, weren’t just a legal headache. They exposed a business model accused of predatory practices and a lack of educational value, damaging his reputation and costing him significant funds.

The Atlantic City Debacle: A Case Study in Financial Mismanagement

The story of Trump’s Atlantic City casinos is perhaps the most glaring example of his financial failings. He entered the market with high hopes, believing his name alone would guarantee success. Though, the reality was far different.

1. Overleveraging: Trump heavily borrowed to finance his casino projects, leaving them vulnerable to economic downturns.
2. Poor Market Analysis: He underestimated the competition and overestimated the potential for sustained profitability in a saturated market.
3. Operational Inefficiencies: reports consistently pointed to mismanagement and a lack of focus on customer service.
4. debt Spiral: As revenues declined,the casinos struggled to service their debt,leading to a downward spiral and eventual bankruptcy. This Atlantic City casinos failure serves as a cautionary tale.

Beyond Casinos: Other Notable Losses & Legal Battles

Trump’s financial troubles extend beyond the casino industry. Several other ventures have faced significant challenges.

Trump Steaks: The short-lived trump Steaks venture, launched in 2007, was a commercial flop. Despite attempts to capitalize on his brand, the product failed to gain traction and was quickly discontinued.

Trump Vodka: Similar to Trump Steaks, Trump Vodka was a failed attempt to extend his brand into the beverage market. It was discontinued after a few years due to poor sales.

The Trump International Hotel Las Vegas: while not a complete failure,the hotel faced financial difficulties and was eventually sold at a loss.

Ongoing Legal Costs: The numerous lawsuits and investigations Trump has faced, both during and after his presidency, have incurred considerable legal fees, further straining his finances. These include investigations into his business practices, campaign finance violations, and the January 6th insurrection. The Trump legal battles are a significant financial drain.

The impact of the New York Civil Fraud Trial (2024)

The 2024 New York civil fraud trial brought to light extensive evidence of inflated asset values and deceptive business practices. Judge Arthur Engoron ruled that Trump, his sons, and the Trump Organization engaged in years of fraud, ordering them to pay over $350 million in penalties.

Inflated Net Worth: The trial revealed that Trump routinely inflated his net worth by billions of dollars to secure favorable loan terms and insurance rates.

Impact on Lending: Banks and lenders relied on these inflated valuations, potentially exposing them to significant risk.

Damage to Reputation: The ruling further damaged Trump’s reputation and raised serious questions about his business ethics. This Trump fraud trial outcome is a major financial and reputational blow.

Real Estate Losses & Valuation Controversies

Trump’s core business has always been real estate, but even here, losses and controversies abound.

Chicago Trump Tower: while seemingly successful, the Chicago Trump Tower faced challenges during the 2008 financial crisis, with sales slowing and financing becoming tough.

Various Property Valuations: Numerous investigations have questioned the accuracy of Trump’s property valuations, alleging that he consistently inflated their worth to boost his perceived wealth.

Foreclosure Threats: Several Trump properties have faced threats of foreclosure due to unpaid debts.

The Role of Debt and Leverage in Trump’s Financial Struggles

A common thread running through Trump’s financial failures is his reliance on debt and leverage. While using debt can be a legitimate business strategy, Trump frequently enough took on excessive amounts of debt, leaving his ventures vulnerable to economic downturns and unexpected challenges.This Trump debt leverage strategy proved consistently risky.

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