Donald Trump’s ‘Obsession’ With Debra Messing Detailed in New Book

Donald Trump’s yearslong “obsession” with actress Debra Messing has been detailed in a new book for which the former president was interviewed several times.

Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, a new book written by Variety co-editor-in-chief Ramin Setoodeh, delves into behind-the-scenes details of the reality contest that transformed businessman Trump into a celebrity. Trump was the show’s host for 14 seasons from 2004.

One of the more unexpected elements of the book, which was released on June 18, reveals how Trump spoke about Will & Grace star Messing on several occasions when being interviewed for the book, asking questions about her and revealing his attraction to her.

Ahead of Apprentice in Wonderland‘s release, journalist Yashar Ali shared excerpts from the book in a Substack article bearing the headline, “Trump’s Obsession With Debra Messing.” It is alleged that Messing once praised Trump for “saving” NBC, which at the time was airing both of their hit shows.

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

It was also stated that Trump would speak of Messing’s “beautiful red hair” and describe her as “quite attractive” on “multiple occasions.” He also depicted her as traitorous. Having once praised him and his show, which was created by Mark Burnett, she has now turned against the former president.

Newsweek has contacted representatives of Messing and Trump via email for comment.

Their First Meeting

“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,” reads an excerpt from Setoodeh’s book.

“‘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.'”

Setoodeh writes how he pointed out to Trump that sitcom Will & Grace aired before The Apprentice and this would not have benefited from the latter’s ratings performance.

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

The excerpt continues: “‘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.”‘ As he makes this claim, Trump’s words are lathered with a suggestive grease, similar in tone to his boasting about women finding him irresistible in the leaked Access Hollywood tape.

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

Messing has been a vocal critic of Trump since he embarked on his presidential run for the 2016 election. Back in 2020, Messing shared a social media post in which she compared the then-president to Adolf Hitler.

‘Can’t Shake the Hypocrisy’

Trump’s purported fixation, per the excerpt, was based on the erstwhile real estate mogul’s feeling that Messing had ultimately betrayed him with her public swipes.

Reads another part of the book on the matter: “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.”

Trump is quoted as saying that Messing was “begging for acceptance” as she purportedly told the businessman what he had “done” for her show and NBC “will never be forgotten.”

“‘Well,’ he proclaims, ‘it was forgotten. 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 further quoted as saying.

Trump’s ‘Crush’ on Messing

“The next time we talk, Trump brings up Messing again, and he confirms something that he’d only dropped hints about in our last meeting,” Setoodeh writes. “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.

“‘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.’

“Then he starts to quiz me about whether or not [Messing’s Will & Grace co-star] Megan Mullally ever betrayed him. As he comes up empty on that front—clearing her of any backstabbing behavior for now—he finally says, ‘You should tell that Debra Messing story. To me, it’s disgusting.'”

Clad in denim overalls and a straw hat, Trump famously joined Mullally to sing the theme song from classic TV show Green Acres together at the 2005 Primetime Emmy Awards.