‘Dagger to his heart’: New book reveals celebrity crush Trump can’t get over

Donald Trump is seemingly obsessed with Will & Grace star Debra Messing, a former NBC colleague turned high-profile critic.

Variety co-editor in chief Ramin Setoodeh interviewed the former president extensively in 2021 and 2023 for his book “Apprentice in Wonderland,” and he said Trump frequently mentioned the actress and Democratic activist, according to excerpts published by The Daily Beast.

“Trump brings up Messing again,” Setoodeh wrote. “He confirms something that he’d only dropped hints about in our last meeting. During the early years of The Apprentice, Trump even had a crush on Will & Grace’s leading lady. Maybe that’s why he can’t quite shake the bitterness that now exists between them.”

“A former president who can’t win over a star almost sounds like the premise of a corny romantic comedy, but for Trump, Messing’s rejection is still a sharp dagger to his heart,” Seteoodeh added. “‘This Debra Messing, who I always thought was quite attractive — not that it matters, of course…’ Their squabbles on social media continue to live rent-free in his mind. ‘Debra Messing was so thankful,’ he says. ‘And then I watch her today, and it’s like she’s a raving mess.’”

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Trump insulted fellow reality TV stars Caitlyn Jenner, who’s now a supporter and Mar-a-Lago regular, and Khloe Kardashian, and claimed that his “macho swagger” reminded others of Clint Eastwood, and Setoodeh recounted a a “disturbing” encounter between the Apprentice star and a younger contestant.

“After a task with the Home Depot — during which the contestants were supposed to create a customized experience for shoppers — the Apprentice house was abuzz about what Trump had supposedly said to Erin Elmore, a 26-year-old attorney from Philadelphia, in the boardroom,” Setoodeh wrote. “On the episode, she’s seen flirting with Trump, even winking at him before she gets the boot. But at some point, Trump allegedly boasted to her, ‘I’ll show you my nine-inch power tool,’ as she pleaded ignorance about her knowledge of home repair.”

“Trump didn’t get in trouble for it,” the author added. “Indeed, since the moment didn’t make it to air, it might as well never have happened. ‘There’s no truth to it,’ says Elmore, a Republican strategist who worked as a surrogate for Trump’s 2016 presidential campaign. ‘It’s kind of hearsay.’”