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Ex-Trump official says 'self-imploding' president was just 'baited' into 'worst' move
October 29, 2026 11:22AM ET
Donald Trump delivering a speech at a campaign rally held at the Mohegan Sun Arena. (Evan El-Amin / Shutterstock.com)
Former Trump administration official Miles Taylor says former President Barack Obama needed just one joke to get President Donald Trump to undercut his own party days before the midterms.
“It took Barack Obama one joke to get the president of the United States to sabotage his party’s midterm election chances,” Taylor wrote in his DEFIANCE.org newsletter on Thursday. He argued that a fight over the Cheesecake Factory “has baited Trump into making the worst, most self-defeating ‘closing argument’ in the history of American elections.”
Taylor served as chief of staff at the Department of Homeland Security during Trump’s first term and later revealed himself as the “Anonymous” author of a 2018 New York Times op-ed critical of the president.
At a rally in Cleveland on Saturday, Obama said Trump has the White House “looking like Saddam Hussein opened a Cheesecake Factory.” Taylor wrote that 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,” Taylor wrote. “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.”
Taylor said Trump attacked Obama on Truth Social that night and again on the tarmac Monday, when he called Obama a “lousy president.” At a Mississippi rally meant to help shore up an at-risk GOP Senate seat, Taylor wrote, Trump then spent roughly 10 minutes defending his gold trim, marble, helipad and ballroom.
“It’s not money. It’s peanuts,” Trump said at the rally, according to Taylor. “We built the most magnificent ballroom you’ve ever seen… 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,” Taylor wrote. He said he was on set at CNN when the network aired a supercut of the remarks, and that the panelists “could barely hold back their laughter.”
Taylor also pointed to Trump’s boast that “we’re making a freaking fortune” from oil while Americans pay more at the pump. He cited Trump’s suggestion in Corpus Christi that supporters spend his promised $5,000 checks at Mar-a-Lago, which Trump followed by warning that “for $5,000, the most you’ll be able to buy is a hamburger and maybe a small dessert.”
“Marie Antoinette must’ve been smiling from the grave,” Taylor wrote.
In under a week, he argued, Trump’s comments “went from self-defeating… to self-destruction… to full-on political self-immolation.”
Obama noticed. At a rally in Atlanta on Wednesday, he mocked the administration for mounting “a whole-of-government response to that joke. Not to inflation, but to that joke.”
“The former president knew he’d walked the current one into a trap,” Taylor wrote. “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.”