President Donald Trump's version of the America 250 celebrations is named "Freedom 250" and it's causing a lot of confusion among those who have been asked to performPresident Donald Trump's version of the America 250 celebrations is named "Freedom 250" and it's causing a lot of confusion among those who have been asked to perform

Inside Trump's humiliating attempt to turn America's birthday into a political rally

2026/06/08 19:01
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President Donald Trump's version of the America 250 celebrations is named "Freedom 250" and it's causing a lot of confusion among those who have been asked to perform at the various events. The big concert for the "America 250" wasn't supposed to be political, but once it came out that Trump would be a big part of it, artists began to withdraw. Trump then announced he didn't want them anyway.

Greg Sargent at The New Republic mocked Trump's moves as his own version of "you're not breaking up with me! I'm breaking up with you!"

In his Monday morning podcast, Sargent, the site's senior editor, Alex Shephard, and the two mocked Trump's knack for turning the 250 events into one of his "embarrassing" MAGA rallies.

"And it’s even more embarrassing than that that you’re doing a rally with Lee Greenwood, who, by the way—I had to look this up before—is even older than Donald Trump," Shephard said. "I think it does kind of capture where we are, less than two years into the second term."

Shephard has spent the past ten years following Trump's efforts to turn his movement into the pop-culture mainstream.

"There was a sense that for the first time since his movement really started in the summer of 2015, there was carte blanche to just love Trump if you wanted to, or to embrace Trump without repercussions," he said. "People have obviously always embraced him, but there’s always been a sense that doing so would have professional, personal, familial, whatever repercussions you can think of.

As he approaches the second half of his last term, he's continuing to insert himself into the zeitgeist.

"And you saw this too—things like there was a UFC fight right after the election and Joe Burrow, the quarterback for the Cincinnati Bengals, embracing him," recalled Shephard. "And it just kind of felt like something that wasn’t there before. And it felt alarming because it seemed like there were just inroads, particularly with whatever we call it, the man-o-sphere now, but even bigger than that. NFL, U.S. men’s soccer, these kinds of things. And even some hip-hop music too."

It hasn't worked out very well, Shephard explained. In fact, it backfired fairly spectacularly.

"It’s just all gone. None of it’s there," he said.

Among those who had been named by Trump to join his 250 events is Omarosa Manigault Newman, a business personality on his former show, "The Apprentice." Even she withdrew from participating.

MAGA figure Matt Walsh said that he's been furious that Trump has bungled the America 250 events by trying to recruit "washed-up geriatric one-hit wonders." But those were the only options that Trump had. That's when he threw up his hands and decided to turn the big concert into another Trump rally.

Sargent said this has a lot to do with how the Trump campaign tried to frame former President Joe Biden as too old and to imply that he wasn't as cool as Trump could be. Meanwhile, MAGA was crafting TikTok videos that tried to paint Trump as an ally for them only to find out Trump was "just lying to them."

"And that was a weirdly devastating moment. But Trump and MAGA just p—ed away the chance that was created for them by this weird confluence of circumstances, I think, he added."

Shephard took the discussion further, saying that examining the MAGA movement and where it goes after Trump will be a key challenge because Trump doesn't like to share the spotlight with anyone. He must be the main event. So, there likely won't be a passing of the torch onto a successor because Trump will never be able to leave the stage.

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