Book Reveals Trump’s Crush on THIS Celebrity Whose Rejection Was ‘A Sharp Dagger to His Heart’

There's a long list of women who reportedly turned former president Donald Trump's advances, but none stings him quite like this one celebrity, a new book has revealed. The business tycoon said he had a thing for actress Debra Messing, complimenting her on her “beautiful red hair,” but he is still irritated by her rejection of him.

In his latest book, Apprentice in Wonderland, co-editor-in-chief of Variety Ramin Setoodeh claims that the Will & Grace actress, now an outspoken opponent of Trump, came up multiple times throughout the six interviews Trump gave Setoodeh, per The Daily Beast.

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 journalist Yashar Ali, who received an advance copy of the book. The book also details how the former president's relationship with Messing soured when she started criticizing him publicly following his 2016 presidential run.

Messing even compared Trump to Adolf Hitler in a social media tweet that she uploaded 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," Seteoodeh 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.’”

In his book, Setoodeh is looking at Trump's ascent to fame on television through The Apprentice and The Celebrity Apprentice, before he entered politics and took 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 looked unlikely to win it again, and in 2023, when it was beginning to look likely that he would win the GOP nomination for a third time.

This book recently made headlines when it disclosed another celebrity Trump was obsessed with: Taylor Swift. Trump spoke of his opinion on Swift, per 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!”