“A Sharp Dagger to His Heart” Trump Still Stings from Debra Messing’s Rejection

 “A Sharp Dagger to His Heart” Trump Still Stings from Debra Messing’s Rejection

Joshua Roberts / Reuters

There’s a long list of women who reportedly turned down former President Donald Trump’s advances, but none stings him quite like actress Debra Messing, a new book reveals. The business tycoon admitted he had a thing for the “Will & Grace” star, complimenting her “beautiful red hair,” but her rejection continues to irritate him.

In his latest book, Apprentice in Wonderland, co-editor-in-chief of Variety Ramin Setoodeh claims that the outspoken opponent of Trump came up multiple times throughout the six interviews Trump gave Setoodeh, according to The Daily Beast.

The former president “repeatedly brought up Messing unprompted in multiple sit-down interviews with Setoodeh,” praising 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 journalist Yashar Ali, who received an advance copy of the book. The book details how Trump’s relationship with Messing soured when she began criticizing him publicly after his 2016 presidential run.

Messing even compared Trump to Adolf Hitler in a social media tweet she posted in 2020. “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 part of the book, the author details Trump’s feelings about the bitterness: “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,” Setoodeh added. “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.’”

Apprentice in Wonderland explores Trump’s ascent to fame on television through “The Apprentice” and “The Celebrity Apprentice,” before his entry into politics and eventual control of the Republican Party, the White House, and the national narrative.

Interviews for the book were conducted between 2021 when Trump had just lost the presidency and seemed unlikely to regain it, and 2023 when he appeared likely to win the GOP nomination for a third time.

The book recently made headlines for disclosing another celebrity Trump was fixated on: Taylor Swift. Trump expressed his opinion on Swift, as reported by The Independent: “She’s got a great star quality. She really does.”

He continued, “I think she’s beautiful — very beautiful! I find her very beautiful. I think she’s liberal. She probably doesn’t like Trump. I hear she’s very talented. I think she’s very beautiful, actually — unusually beautiful!”

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