Trump’s Obsession With Debra Messing

In a new book about ‘The Apprentice,’ the former President seems to be obsessed with the actress, bringing her up repeatedly in interview after interview, and admitting that he once had a crush on her

One of the more bizarre revelations in Ramin Setoodeh’s book about ‘The Apprentice,’ which comes out tomorrow, is that former President Trump seems to be obsessed with actress Debra Messing, the star of the hit NBC sitcom ‘Will and Grace’ and one of the most vocal celebrity activists who repeatedly used her platform to slam Trump on a myriad of issues.

Setoodeh, the co-editor of Variety and the author of the definitive behind-the-scenes book about ‘The View,’ sat down with Trump six times for his book, ‘Apprentice in Wonderland,’ which offers a detailed behind-the-scenes look into the show, which boosted Trump’s public profile to new heights and aided his campaign for the presidency.

• Trump admitted that he spent time while in the White House monitoring Messing’s Twitter feed.

• Trump repeatedly brought up Messing unprompted in multiple sit-down interviews with Setoodeh.

• He admitted to Setoodeh that he had a crush on Messing years ago.

• On multiple occasions, he would simultaneously compliment Messing on her looks, saying she had “beautiful red hair” and that she was “quite attractive,” while in the same breath saying she was traitorous for once — allegedly — praising him when they both had shows on the air at NBC.

• He grilled Setoodeh on whether or not Messing’s co-star, Megan Mullally, ever betrayed him like he accuses Messing of doing.

Even though the public has become familiar with Trump’s storytelling style, it’s important to remind my readers that Trump’s stories about how others react to him are often filled with embellishments and outright lies.

Here are some excerpts from Setoodeh’s book, which I obtained and read three weeks ago, about Messing:

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.

“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.”

I point out to Trump that Will & Grace came on before The Apprentice, which would mean that it wouldn’t have received a ratings bump from viewers tuning in to The Apprentice. “A lead-in—or a lead out,” he clarifies.

“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.”

Trump kept bringing up Messing with Setoodeh in interview after interview:

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. “She probably wouldn’t even admit it,” Trump says about Messing’s supposed flattery from more than fifteen years ago. “She came up to me in front of a group of people. I’ve never seen it. She was begging for acceptance!” He takes on a higher-pitched voice that’s supposed to be Messing: “Thank you so much for what you’ve done for me, my show, and for NBC. It will never be forgotten.”

Trump pauses dramatically. “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.”

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. 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 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.”

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