Donald Trump’s biographer says TIME’s cover photo carried extra sting for the president, not just because of his unflattering hair and neck, but due to his long-held obsession with the magazine.
TIME unveiled the cover for its latest issue Monday, which features Trump alongside a glowing article about his role in brokering the Gaza ceasefire deal. “His Triumph,” the magazine declares in its all-caps cover line, beside a low-angle photo of Trump gazing into the distance.
Despite the magazine’s fawning language, however, the looks-obsessed president couldn’t help complaining about the photo choice. He fired off a furious Truth Social post at 1:30 a.m. Washington time Tuesday, fuming that the picture TIME published on its cover “may be the Worst of All Time.”
“They ‘disappeared’ my hair, and then had something floating on top of my head that looked like a floating crown, but an extremely small one,” Trump wrote. “Really weird! I never liked taking pictures from underneath angles, but this is a super bad picture, and deserves to be called out. What are they doing, and why?”
Inside Trump’s Head podcast hosts Michael Wolff and Joanna Coles both agreed that Trump’s dissatisfaction with his latest cover photo, which emphasizes his neck and thinning hair, isn’t unfounded.
“He is right about that. That angle,” Wolff said. “You never want someone to take a picture from below, which is a technique that the media or the print media uses when they want to diss somebody.”
“This is not a flattering shot,” Coles added, noting that the editor-in-chief of the left-leaning media company Meidas Touch, Ron Filipkowski, had dubbed the skin around president’s neck a “neck vagina.”
Filipkowski responded to Trump’s whining post on X Tuesday morning, writing, “They showed his neck vagina. That’s what he’s really upset about.”
They showed his neck vagina. That’s what he’s really upset about. pic.twitter.com/w9btQWOFHu
— Ron Filipkowski (@RonFilipkowski) October 14, 2025
The 79-year-old president appears to have typed out the Truth Social post mid-flight on Air Force One, en route home from his Middle East victory lap to tout the peace deal.
Wolff said that the president is “still obsessed with TIME,” even as the iconic magazine has experienced declining circulation and shrunken operations.
Wolff said that at a “pivotal moment” during his 2024 campaign, Trump canceled a flurry of events “because TIME magazine called him up.”
“They gave TIME magazine a full day,” Wolff told Coles, “with everybody saying on the campaign staff, ‘TIME? Why are we doing this for TIME? Does anyone read TIME?’”
When reached for comment, White House Communications Director Steven Cheung told the Daily Beast, “Michael Wolff is a lying sack of s–t and has been proven to be a fraud. He routinely fabricates stories originating from his sick and warped imagination, only possible because he has a severe and debilitating case of Trump Derangement Syndrome that has rotted his peanut-sized brain.”
The Daily Beast has reached out to TIME for comment.
Trump’s fascination with the magazine apparently goes so deep that he once displayed fake covers bearing his image in his golf clubs—until TIME asked for them to be removed.
Luckily for him, he has no shortage of authentic covers to display. Trump is closing in on former President Richard Nixon’s record for most TIME covers. When the magazine named Trump Person of the Year in December 2024, it marked his 43rd cover appearance.
Wolff speculated that, unlike the cover story “How the Trump Administration Sealed the Gaza Ceasefire Deal,” the cover itself was likely not sent to TIME’s billionaire owner Marc Benioff before it was published.
The Salesforce CEO, once viewed as relatively liberal, recently outed himself as an enthusiastic Trump supporter, telling The New York Times that the president should send the National Guard into San Francisco.
Benioff, who bought TIME for $190 million in 2018, was reported to be in talks to sell the magazine last November, although he later said no such deal was being considered.
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