Trump's Freedom 250 implosion proved there's one thing he can't conquer: analysis
Construction is underway on a temporary arena that will host the UFC Freedom 250 fight card in June, while ongoing construction on the planned White House ballroom in the area of the former East Wing continues at the White House in Washington D.C., on May 28, 2026. REUTERS/Kylie Cooper

President Donald Trump's "epic crashout" after most of the performers bowed out of his "Freedom 250 Concert" revealed that the commander-in-chief cannot seem to get his grip on what he desperately wants: cultural relevance, a journalist pointed out on Monday.

In a Substack post, author Paul Waldman described how "his quest to dominate culture the way he dominates politics keeps going badly," and his most recent move backfired. A majority of the artists ended up dropping out and some said they were misled to think it was a nonpartisan event, but "once they realized the event was all about Donald Trump, most of them wanted nothing to do with it."

This was a nightmare for Trump, Waldman explained.

"So Trump’s long-held dream to take over American culture in the same way he took over American politics remains unfulfilled," Waldman wrote. "For all the ways he has affected the country, he is not a tastemaker or an avatar of coolness; when the culture speaks of Trump, it’s mostly to rail at him and reject him."

And his meltdown over the weekend after the party started to fall apart prompted him to cancel it altogether and instead plan a rally — despite Vanilla Ice's enthusiasm to still perform.

"It’s not just that he has terrible taste, though of course he does," Waldman added. "It’s unclear how many people are splashing their own homes in hideous gold-painted appliqués to mimic his Russian-gangster-meets-Saddam-Hussein aesthetic, but there can’t be all that many. Trump’s musical tastes run from show tunes to perfectly adequate pop numbers to one particular ‘70s song about gay men cruising for sex — but the last thing you’d call him is cool."

As Waldman argued, "even if Trump imagines himself bigger than Elvis," he simply isn't.

"Donald Trump may be a showman, but he doesn’t really know how to put on a show — at least one that anyone but his most rabid supporters will want to attend (and even they’re getting tired)," Waldman added.