Inside Trump’s deeply weird ‘obsession’ with Debra Messing — and her ‘beautiful red hair’

‘Their squabbles on social media continue to live rent-free in his mind’

Martha McHardy
Tuesday 18 June 2024 15:26 BST
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Donald Trump has a bizarre obsession with Debra Messing and her ‘beautiful red hair,’ according to a new book
Donald Trump has a bizarre obsession with Debra Messing and her ‘beautiful red hair,’ according to a new book (Getty)

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Taylor Swift isn’t the only “beautiful” celebrity Donald Trump has openly gushed about.

According to a new book, the former president admitted to having a crush on actor Debra Messing — praising her “beautiful red hair” — and is still annoyed by her very public rejection of him.

Variety co-editor-in-chief Ramin Setoodeh reveals in his new book, Apprentice in Wonderland, that theWill & Grace star, who has been a vocal critic of Trump’s since he first ran for president in 2016, came up several times during their six interviews.

According to journalist Yashar Ali, who obtained an advanced copy of the Apprentice book, the former president “repeatedly brought up Messing unprompted in multiple sit-down interviews with Setoodeh,” complimented her “attractive” appearance, and “admitted that he spent time while in the White House monitoring Messing’s Twitter feed.”

Trump also “admitted to Setoodeh that he had a crush on Messing years ago,” according to Ali.

In one excerpt from the book, Trump claimed that Messing once approached him “with her beautiful red hair” and thanked him for “saving” NBC with his show The Apprentice.

“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,” Trump told Setoodeh. “She was so thankful… 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.’”

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

Debra Messing has been critical of Trump since 2016
Debra Messing has been critical of Trump since 2016 (Getty Images for Project Angel F)

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

According to the report, the book also documents how the former president’s feelings towards Messing turned sour when she began to openly criticize him after he launched his 2016 presidential bid. In 2020, Messing even shared a social media post in which she compared Trump to Adolf Hitler.

“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,” Setoodeh wrote.

In another excerpt, he added: “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.”

“Their squabbles on social media continue to live rent-free in his mind,” Ali added.

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