Trump’s Unshakable Obsession with Debra Messing ‘A Sharp Dagger to His Heart’

 Trump’s Unshakable Obsession with Debra Messing ‘A Sharp Dagger to His Heart’

(AP Photo/Rick Scuteri)

Donald Trump appears to be fixated on “Will & Grace” star Debra Messing, a former NBC colleague and now a prominent critic. In his book “Apprentice in Wonderland,” Variety co-editor-in-chief Ramin Setoodeh reveals Trump’s frequent mentions of the actress during interviews conducted in 2021 and 2023. Excerpts published by The Daily Beast highlight this unexpected focus.

“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.”

Setoodeh describes the situation as almost comedic, likening it to a romantic comedy premise. “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,” he wrote. “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.’”

The book also delves into Trump’s other interactions with celebrities and reality TV stars. He insulted Caitlyn Jenner, now a supporter and Mar-a-Lago regular, and Khloe Kardashian. Trump even claimed his “macho swagger” reminded others of Clint Eastwood.

Setoodeh recounts a “disturbing” incident involving Trump and a younger contestant on “The Apprentice.” “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.”

Despite the controversy, Trump faced no repercussions for the alleged comment, which did not air. “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.”

Setoodeh’s book, “Apprentice in Wonderland,” offers a revealing look into Trump’s post-presidency interactions and enduring ties to his television past. His fixation on Debra Messing and the controversies surrounding his behavior continue to paint a complex picture of the former president.

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