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Barack Obama tricked Donald Trump into self-imploding just before the midterms.

A fight over the Cheesecake Factory has baited Trump into making the worst, most self-defeating "closing argument" in the history of American elections.

Miles Taylor's avatar
Miles Taylor
Oct 29, 2026
∙ Paid

It took Barack Obama one joke to get the president of the United States to sabotage his party’s midterm election chances.

Last Saturday in Cleveland, Obama walked rally-goers through the absurdity of Trump’s gold-leafed Oval Office, the paved-over Rose Garden, the helipad, and the billion-dollar ballroom-bunker complex rising where the East Wing used to be. He summed it up in a sentence: Trump has the White House “looking like Saddam Hussein opened a Cheesecake Factory.”

It was a funny throwaway line in a speech about corruption and the cost of living. And the real point was that the sitting president is so out of touch that he’s redecorating his palace while Americans can’t afford groceries.

And Trump couldn’t let it go. So much so that he began a multi-day process of self-implosion, the likes of which we’ve rarely seen burn so brightly in American politics.

First, Trump attacked Obama on Truth Social that very night… and again on the tarmac Monday, calling him a “lousy president.” Then, he flew to Mississippi, stood in front of a rally that was supposed to be focused on saving an at-risk GOP Senate seat, and kept circling back to the Obama insult. Not one or two times. But for roughly ten minutes. Ten minutes of Trump visibly flustered by the whole ordeal and defending his gold trim, the marble, his new granite helipad, and the ballroom to people who came to hear about their jobs.

I was on set at CNN that night as they aired a supercut of it. You had to see it to believe it.

“We have the most beautiful marble,” Trump protested, trying to persuade his audience. “It’s not money. It’s peanuts. We built the most magnificent ballroom you’ve ever seen. It’s under construction. It’s ahead of schedule. Barack Hussein, he didn’t talk about that. He talked about the ballroom that, he spends all his time thinking about the ballroom. That has to be pristine. And I would try and explain that to a guy like Obama, but he wouldn’t understand.”

Oh, Mr. President, I think Obama understands very well.

The liberal and conservative panelists on set with me at CNN could barely hold back their laughter. I might’ve been in the worst shape. I was having trouble composing myself as we came back from the clip.

Americans already knew what Obama was talking about. We’ve watched Trump’s fixation with redecorating the White House pretty much swallow him whole. In March, two days after he ordered the strikes that started the Iran war, Trump used a Medal of Honor ceremony to gush about his ballroom instead of addressing the solemness of the ceremony or the fact that we were at war.

“I picked those drapes in my first term,” he smiled to attendees. “I always liked gold.”

Meanwhile, gas prices were beginning to soar as the bombs dropped.

But this week when he was called out for it, Trump’s descent into self-destructive territory didn’t stop with his defensive response to Obama. Remarkably, he confessed to another rally crowd that his own advisers had begged him not to brag about oil profits while people were paying $4.29 a gallon. But he bragged anyway.

“I don’t give a damn, I’m going to say it. We’re making a freaking fortune!” he gushed to what I imagine must’ve been a confused audience.

Who is the “we” in this sentence? It’s certainly not the people at the pump. Presumably, the president was bragging about the U.S. oil companies themselves posting record profits off a war he started. Somehow in his twice-warmed-over microwaved mind, he wants his followers to think that counts as a win for the family filling up their minivan. Don’t worry, he assures them, all the cash you’re forking over to the oil execs will, you know, trickle back down to you… someday!

That right there — those absurd comments — could’ve set the record for the most out-of-touch thing a president has said on the eve of an election. Ever. But he didn’t stop there.

Tuesday night in Corpus Christi, Trump brought up the $5,000 checks he’s promised to send Americans if and only if Republicans keep Congress. In a bizarre moment, he invited the crowd to spend the money on him… at his own club… as his guests at Mar-a-Lago. Then, he seemed to remember how high his own club’s prices actually were.

“For $5,000, the most you’ll be able to buy is a hamburger and maybe a small dessert. I’m not even sure you could buy that,” he said. “No, don’t go there. That’s not a good place if you’re price-conscious.”

Marie Antoinette must’ve been smiling from the grave. Finally, “let them eat cake” had been supplanted by something an order of magnitude more callous.

Trump’s closing argument on corruption and affordability — the two issues voters say matter most — seems to boil down to this: Don’t worry about my renovations, they’re beautiful, and that’s good for America. Also, if gas prices bother you, just be happy that my oil friends are getting rich. And if you’re still upset, come have a burger at my club, which you can’t afford even with the $5,000 I’m dangling, so on second thought don’t bother, poor people.

In a window that he’s supposed to be “on message,” Trump’s comments went from self-defeating… to self-destruction… to full-on political self-immolation in less than a week.

So last night in Atlanta, Obama couldn’t resist:

“He’s literally doing arts and crafts while we’re fighting a war and trying to deal with out-of-control prices,” he said, laughing. “The president wasn’t even mad about the Saddam Hussein comparison. That part didn’t bother him. But he was very upset about the Cheesecake Factory comments.”

Then the part he clearly savored:

“They mobilized a whole-of-government response to that joke. Not to inflation, but to that joke. Y’all didn’t see this? This really happened. And the Treasury Secretary, who happens to be worth half a billion dollars, he’s out there in front of the Cheesecake Factory explaining how he ordered the delicious French dip cheeseburger instead of the egg rolls.”

The former president knew he’d walked the current one into a trap. Days before an election, he’d gotten Trump on his back foot, defending indefensible corruption and mocking the plight of the people themselves. The people who will vote on November 3 whether to re-hire or fire Trump’s enablers.

Last week ended with Obama making a joke. This week, Trump took it as poorly as you could possibly imagine. And next week, voters will have the last laugh.

Your friend, in defiance,

Miles Taylor

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