Long before he called Taylor Swift “unusually beautiful,” it was Debra Messing who had Trump utterly entranced. According to a new book giving a behind the scenes look at The Apprentice, Messing’s “beautiful red hair” captivated Trump since they first met in the early 2000s and still continues to due so. A longtime critic of the former president, the Will & Grace star now has Trump caught between bitter resentment and desire.
Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, written by Variety co-editor-in-chief Ramin Setoodeh, chronicles Trump’s complex feelings for the actress. Over the course of several sit-down interviews with Setoodeh, Trump admitted that he had a crush on Messing years ago and spent time while in the Oval Office monitoring her Twitter feed. Cockburn suspects that this was his biggest obstacle ditching the platform for Truth Social.
Trump still remembers his first time meeting Messing all these years ago. She had allegedly come up to the former president at a NBC during the second season of The Apprentice, thanking him for bolstering the network’s ratings and “begging” for his acceptance. “‘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.’”
According to Setoodeh, Trump still lusts after Messing’s “beautiful red hair,” although he has placed her on “his traitor list” since leaving the White House. Messing earned special ire from Trump after threatening to blacklist his supporters in Hollywood, even after her promise never to forget what he did for the network. “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 has continued attempts to overcome his unrequited love, calling Messing a “raving mess” — although Cockburn doubts he ever he will escape the allure of the redheaded siren.
Trump’s latest fear is that Megan Mullally, the other Will & Grace star, will betray him as well. It’s a little late for that since Mullally has already distanced herself from the former president. After Trump shared a clip of the two performing the Green Acres theme song at the 2005 Emmy Awards, Mullally was quick to voice her displeasure. “If you guys need me, I’ll be in a hole in the ground,” she posted to X and later said she preferred Trump when he was a “harmless boob.”
