'Take me to court': Conservative says Trump is weaker than he claims

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U.S. President Donald Trump attends the commencement ceremony at West Point Military Academy in West Point, New York, U.S., May 24, 2025. REUTERS Nathan Howard

Bulwark podcaster and conservative pundit Tim Miller said the fight against President Donald Trumps’s attack on free speech would be easy to beat back, if people found the will.

“He's trying to intimidate,” Miller said of the administration’s strong-arm removal of late-night comedian Jimmy Kimmel. “That's what this is. He did it with the universities. He did it with the law firms. And now he's going after the networks. And he's testing everybody. This is why what Disney CEO Bob] Iger did is so shameful, I think, in folding.”

Speaking to podcast guest Katie Couric, founder of Katie Couric Media, Miller said Trump’s threats to the entertainment industry are easily stomped in courtrooms as constitutional violations.

“What you should be doing is saying, ‘okay, sure. Take me to court. Take my license. Let's see it,” said Miller, who remains confident companies would prevail all the way up to the Republican-dominated Supreme court.

“I think there's a pretty big majority on the Supreme Court that’s for the First Amendment,” said Miller. “You might not like the Supreme Court's views on a bunch of other stuff but do what Trump would do to you: Take him back to court. Kick the can. Run the clock. … What was Brendan Carr actually going to do to the Jimmy Kimmel show? Nothing. … [H]is intimidation tactics only work if people get intimidated.”

And while the Constitution should easily prevail in court, Miller predicted opposition was also building on the ground level against Trump’s anti-democratic attack against free speech.

“The red hat folks that go to the rally, they signed up for the vengeance. They signed up for the culture war. They're happy to see Jimmy Kimmel go down. They bought the ticket for that ride, like a lot of MAGA voters,” said Miller. “But that was not the case for a lot of people that came to Trump late.”

Trump is already losing ground with some MAGA elements

“I've seen some MAGA comedians I follow — Tim Dillon, Andrew Schultz — speaking out against it,” said Miller. “… Not everyone's ever going to turn on him. Obviously, Fox [News] was never serious about their free speech concerns. It was always partisan positioning. But there are some people out there who were serious, and it's time for them to step up now.”

Watch the podcast at this link.

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