2024 Election

Trump Admits He Had a ‘Serious Crush’ for Actress Debra Messing, Bordering on ‘Obsession’

Donald Trump has always been obsessed with beautiful women, which is, of course, not unusual for most men, but his obsession has been, well…pretty unhealthy and frankly, creepy. The new book, Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass by Ramin Setoodeh, Variety’s co-editor-in-chief, showcases Trump’s bizarre obsession with actress Debra Messing while highlighting behind-the-scenes details of the reality contest that turned Trump into a celebrity.

One aspect of the book, which was released on June 18, that is well, weird, is Trump continually talked about Will & Grace star Messing on numerous occasions as he was being interviewed for the book. This includes doing things like asking questions about her and revealing his attraction to her, Newsweek reports.

Prior to the book’s release, journalist Yashar Ali shared excerpts from the book in a Substack article titled Trump’s Obsession With Debra Messing. Allegedly the actress once praised Trump for “saving” NBC, which was airing both hit shows.

Ali, guessing at Trump’s thoughts, wrote that Trump “admitted that he spent time while in the White House monitoring Messing’s Twitter feed,” and “repeatedly brought up Messing unprompted in multiple sit-down interviews with Setoodeh.” He also “admitted to Setoodeh that he had a crush on Messing years ago.”

Trump also talked incessantly about Messing’s “beautiful red hair” and described her as “quite attractive” on “multiple occasions” and then subsequently described her as traitorous. She may have praised him and his show, which was created by Mark Burnett, but she sure doesn’t do that now.

“Trump still remembers the day he met Messing—who played the self-centered New York interior designer Grace Adler on NBC—around the time of The Apprentice’s second season,” one excerpt from Setoodeh’s book reads.

“‘So I’m in line,’ Trump recalls. ‘The show had gone to No. 1, and we’re ready to do the upfronts, which I’d never heard of.’ As a new TV star, he was quickly catching up with Hollywood jargon: upfronts are an annual presentation that networks give in May, trotting out their stars to charm advertisers ahead of the upcoming TV season. ‘And Debra Messing came up to me. She had a show at a similar time.'”

“‘She came up to me with her beautiful red hair,’ Trump says about Messing, pausing on this detail a beat too long. ‘And she said, “Sir—I love you! Thank God for you! You’re saving the network, and you’re saving my show.” Because in that world, which I know a lot about now, when you have a hit, a lead-in, it’s a massive difference.'”

But Setoodeh points out to Trump that Will & Grace aired before The Apprentice, meaning the show wouldn’t have benefitted from The Apprentice’s ratings performance.

“A lead-in—or a lead-out,” Trump then clarified.

And there was more, according to the excerpt:

“‘She was so thankful,’ Trump says. ‘She said, “I can’t thank you enough.” Do you believe this? I’ve been watching her. And I’m saying, “She’d do anything for me.”‘

His words take on a sleazy tone as he claims this, bringing to mind the notorious Access Hollywood tape.

“‘She was so effusive,’ Trump concludes. ‘And when I see the hatred coming out of her mouth today, it’s incredible.'”

This behavior is so typical of Trump. He literally can’t understand it when an attractive woman doesn’t fall at his feet. Once Messing found out how he really was, she turned a corner and she’s been a vocal critic of him ever since he embarked on his 2016 presidential run. In 2020, she shared a social media post where she compared Trump to Adolf Hitler.

And Trump can’t seem to get Messing out of his head.

“Here in New York, during his early months outside the White House, Trump hasn’t moved on. Messing is on his traitors’ list, and he can’t shake the hypocrisy—in his mind—that she once supported him as a reality TV star,” reads another excerpt from Setoodeh’s book.

He believes she was begging for acceptance, and well now, “She was just a nasty person. Her and many others. So many people have come up to me over the years and said, ‘Thank you!’ Once I ran for office, that stopped,” Trump is quoted as saying.

I’m sure that the appreciation came to a screeching halt when people found out what Trump’s true agenda was, and what he planned to do in office. Which was also accentuated by his obvious racism and misogyny.

Messing has rented a room inside his head because he’s still obsessing about her.

“‘This Debra Messing, who I always thought was quite attractive—not that it matters, of course…,'” he says. “Debra Messing was so thankful. And then I watch her today, and it’s like she’s a raving mess.'”

That’s how Trump acts whenever any woman doesn’t kowtow to him in some way or another. He’s the one who’s the “raving mess.” All anyone has to do is to listen to him to find out how truly horrible he really is.

Here’s what Yashar Ali had to say about it.

meet the author

Megan has lived in California, Nevada, Arizona, Texas, Louisiana, Mississippi, and Florida and she currently lives in Central America. Living in these places has informed her writing on politics, science, and history. She is currently owned by 15 cats and 3 dogs and regularly owns Trump supporters when she has the opportunity. She can be found on Twitter at https://twitter.com/GaiaLibra and Facebook at https://www.facebook.com/politicalsaurus


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