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E. Jean Caroll prevails, and Trump keeps losing in court

This week, we’ve got an objectively feel-good story about how President Donald Trump was finally forced to give E. Jean Carroll the money he’s owed her for years. 

That’s a minor bright spot, though, as we’re also learning that Yale University might be knuckling under to Trump and that the already outclassed Justice Department attorneys are going to get even worse.


E. Jean Carroll gets that bag, finally

It only took three-plus years, multiple trips to the appellate court, and a sad “womp womp” from the Supreme Court, but Trump finally had to cough up the $5 million he owed writer E. Jean Carroll.

E. Jean CarrollAP

Carroll prevailed in a lawsuit against Trump where he was found liable for having sexually abused her decades ago, and Trump fought mightily to never pay her.

To be clear, Trump didn’t agree to give Carroll the money. Rather, it was already held in escrow by the court. After both the lower court and the appellate court denied Trump’s request for a stay, the money was finally transferred to Carroll’s attorneys. 

Now, Trump just needs to get her the other $83 million he owes her, thanks to his spectacular loss in her defamation suit. Pay up, buddy. 


Why on earth would you ever cut a deal with Trump?

Seriously, people. Trump has never held up his end of the bargain in his life if he didn’t feel like doing so. There’s no reason to negotiate with him about anything, no reason to see any deal as real, no reason to think that giving him what he wants will stop him from attacking anyway. 

But Yale University seems to have decided that they’re built different, actually, and will somehow come out on top. 

So they’ve entered into talks with the DOJ to resolve the made-up allegation that their medical school is full of forbidden diversity, equity, and inclusion initiatives, which is presumably only resolved by giving the administration hundreds of millions of dollars and agreeing to never admit any women again or something. 

But time and time again, Trump turns on everyone. The possibility of Yale agreeing to settle with a mobster running a protection racket has alarmed Yale professors so much that they’ve retained counsel and intend to fight any so-called settlement. Good on them.  


How many times did states have to sue Homeland Security before, say, 2025? 

In a sadly predictable turn of events, Ramsey County, Minnesota, has been forced to bring suit against the Department of Homeland Security to get them to cough up evidence of crimes by Immigration and Customs Enforcement agents. 

A photo of 37-year-old Alex Pretti, who was fatally shot by a U.S. Border Patrol officer over the weekend, is displayed at the shooting scene Monday, Jan. 26, 2026, in Minneapolis. (AP Photo/Adam Gray)
A memorial in Minneapolis, Minnesota, is set up where Alex Pretti was murdered by immigration agents.AP

Though the administration finally, after six long months, agreed to provide evidence to Minnesota in the murders of Renee Good and Alex Pretti, it’s still refusing to provide evidence from when ICE agents forced their way into the home of U.S. citizen ChongLy Thao and kidnapped him. 

Well, let’s call it what it is, right? They broke down his door, handcuffed him, and frog-marched him out of his house in nothing but underwear and a robe. The Ramsey County attorney is trying mightily to investigate this open and obvious crime, but so far, the administration has stonewalled. 

Somehow, it doesn’t seem normal or good or cool at all that the federal government is at war with blue states, so much so that everything is a pitched court battle just to hold ICE thugs even marginally accountable. 


Trump’s own lower court judges continue to point at him and laugh

Trump has enjoyed a truly remarkable run at the Supreme Court, where the conservative majority almost never tells him no. Indeed, they often just rubber-stamp his wildest ideas without even bothering to explain why.

But when it comes to judges who actually do the work of judging, even Trump’s own appointees are refusing to indulge his worst impulses. 

Take his attempt to seize state voter rolls to ensure that his flailing, unpopular party prevails in the midterms. He’s 0 to 15 in those attempts. You’d think that losing that many times would stop Trump, but you’d be wrong. 

Of those 15 decisions, nine were from GOP appointees, and six were from Trump appointees. It’s such a basic premise—the executive branch has no role in elections, by constitutional design—that even his strongest judicial soldiers must be getting weary of having to explain it. 


DOJ babies about to be saddled with more cases

The DOJ has hemorrhaged experienced attorneys, a product of both mass firings and principled nonpartisan prosecutors fleeing rather than taking part in the shameful degradation of the department. 

A cartoon by Clay Bennett showing a cop labeled "good cop" on Jan. 19, 2021, and that same cop labeled "bad cop" on Jan. 20, 2021.
Clay Bennett/Tribune Content Agency

The administration has solved this by forcing judge advocate general attorneys, who typically do not handle civilian cases, and by continually lowering their hiring standards to the point where you can now get a job straight out of law school. 

But now they have a genius new plan: case quotas.

Yes, the DOJ attorneys who are currently buckling under the weight of the unprecedented number of cases generated by the administration’s persistent lawlessness are being told that they need to handle more of them. 

This doesn’t just mean that these attorneys are going to be even more overworked and outwitted, pressuring prosecutors to bring cases that they shouldn’t bring without sufficient evidence.

But this administration probably considers that a feature, not a bug. 

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