A former staffer from President Donald Trump's first term recalled an anecdote from his very first week in office that has echoed in his mind for years.Miles TaylorA former staffer from President Donald Trump's first term recalled an anecdote from his very first week in office that has echoed in his mind for years.Miles Taylor

Ex-aide recalls 'creepy' story Trump told about 'tough' guy who wept in Oval Office

2026/06/12 21:49
3 min read
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A former staffer from President Donald Trump's first term recalled an anecdote from his very first week in office that has echoed in his mind for years.

Miles Taylor, who served as chief of staff for the U.S. Department of Homeland Security, published a new piece for The i Paper calling back a story – which he said probably never even happened – that Trump liked to tell that he argued helps explain his approach to governance.

Ex-aide recalls 'creepy' story Trump told about 'tough' guy who wept in Oval Office

"I had a front-row seat to the early stages of Trump-induced American decay," Taylor wrote.

From that vantage point, Taylor published a famed anonymous op-ed for the New York Times revealing how some of Trump's first-term advisers acted as a "resistance" to his worst impulses, but he said the president has purged those moderating voices from his orbit in his second term.

"I warned the country that Trump had almost comical parallels to the types of despots that another Roman luminary, Cicero, had warned about millennia earlier," Taylor wrote. "That’s why I titled my forecast, A Warning. I wrote about how, in my early exposure to the president, he bore all the hallmarks of the 'arrogant and dishonourable' men who’d wrecked Rome."

"For instance, I recounted how he took reporters on a tour of the Oval Office during his first week and how he’d already redecorated it with new drapes and a new rug to fit his style," he continued. "That itself isn’t unusual for a new president. What was creepy was that he told those journalists a story about a recent visitor — a tough person, he insisted — who had walked into the room and allegedly started to cry."

That anecdote has rattled around in Taylor's head as Trump plans his UFC birthday brawl this weekend on the White House lawn.

“They see the power of the White House and the Oval Office," Trump said, according to Taylor, "and they think, 'Yes, Mr. President. Who tells you no?'"

"Who tells you no?" Taylor marveled.

Taylor has always suspected the tale was made up, like a lot of Trump stories, but he's never forgotten it.

"I’ve thought about that line for almost 10 years," he said. "At the time, people read it as pure vanity. In hindsight, it was as succinct a presidential thesis statement as we’ve ever heard. In my observation, a man like Trump experienced his office primarily through the thrill of being able to intimidate and coerce people through power, and if returned to power, a man like that was always going to use his office for personal gain at the expense of the polity."

"Given enough time and enough compliant lieutenants, he’d refuse to be told 'no' by anyone or anything, whether it was the Congress, the courts, the Constitution, or even the calendar of his own mortality," Taylor added. "Here we are."

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