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For a guy who hates losing, Trump does it a lot.

The president lost in court again last night — with a judge ordering him to reinstate press badges to CNN, MSNOW, and Politico.

Miles Taylor's avatar
Miles Taylor
Sep 24, 2026
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Donald Trump is his own worst enemy, and last night a federal judge reminded him of that again.

Judge Timothy Kelly ordered the White House to immediately restore the hard passes of reporters from CNN, MSNOW, and Politico, which Trump yanked last week after bemoaning their coverage of him. Kelly found the outlets were likely to win their argument that the passes were pulled without due process, and he wasn’t buying the administration’s national security excuse either.

Government lawyers argued the outlets posed a “national security” threat, pointing to reporting on “top-secret” East Wing bunker construction, leak investigations, and Secret Service security upgrades. One problem: Donald Trump himself already told everyone his real reason: “I think we have a right to clean out fake news.” The “national security” case got even weaker when the White House’s defense cited a June story about Iran negotiations as proof of a leak. The source for the reporting was actually JD Vance, speaking on a White House-sanctioned press call the administration itself set up.

The funny part is that Trump saw this coming. When the case was assigned, he whined on Truth Social that the outlets had drawn a great judge “for them.” Kelly is the same Trump appointee who restored Jim Acosta’s press pass back in 2018. Trump lost this same fight eight years ago… and he picked it again anyway.

Are you seeing a trend here, by chance? Trump says he has enemies everywhere. And he’s right. They seem to be multiplying, but he made almost all of them himself. Just look at his own party right now.

According to the Washington Post, at least seven Republican House candidates in battleground races have scrubbed or downplayed him on their campaign websites. Florida’s Maria Elvira Salazar went further and cut an ad standing in front of the White House saying his immigration crackdown has gone too far. Iowa’s Zach Nunn and Mariannette Miller-Meeks voted with Democrats to try to end Trump’s foolish war with Iran. Candidates who spent years begging for his endorsement are now treating Trump’s blessing like a kiss of death.

Elected Republicans are even starting to turn on him. Republican Senator John Curtis is demanding a subpoena for Don Jr. after ProPublica reported that Umar Kremlev (an oligarch close to Russia’s President Vladimir Putin) helped bankroll his Bahamas wedding party, including a private island and a fireworks show. GOP Senator Thom Tillis called it “colossally bad judgment at best,” and other GOP senators say they’re on board with a probe. Trump’s defense is that his son paid the guy back (which he also can’t seem to confirm).

You can literally map out how badly Trump’s brand is causing the GOP to lose. Republicans are pouring money into deep-red states like Texas, Iowa, Florida, and Alaska, states Trump won easily in 2024, and JD Vance had to fly to Kansas to shore up Senator Roger Marshall for fear that the plains state could swing to the Democrats. That’s what happens when the guy at the top of your ticket is dragging everyone down with sky-high gas prices… a war nobody wanted… and a new corruption story every single day.

I hear from a lot of Democrats who are nervous the momentum against Trump can’t hold for six more weeks. I get it. But trust me on this one, because I worked for the man. He has precisely zero discipline. He can’t go a week without picking a new fight, breaking another federal rule, or doing something that drags his name back into the headlines or into a federal courtroom for all the wrong reasons. He’ll keep doing our work for us.

Just listen to what the MAGA side is saying underneath their breath. Republicans desperately want him to go away before November 3. And he won’t. He’s told voters to pretend he’s on the ballot, and he’ll keep chaining himself to his party right up to election day, even if it’s political suicide.

For a guy who hates losing, he sure seems determined to do it again.

Your friend, in defiance,

Miles Taylor

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