The Unexpected Sitcom Star Donald Trump Reportedly Had A Big Crush On
Variety Co-Editor-in-Chief Ramin Setoodeh's book "Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass" includes details about former President Donald Trump's reality show "The Apprentice." In it, he describes Trump's apparent crush on actor Debra Messing — someone who's far from a fan of his. Messing and fellow actor Susan Sarandon even got into a feud over their feelings on Trump, despite neither wanting to vote for him.
Yashar Ali from "The Reset" Substack received a copy of Setoodeh's book prior to its publication on June 18, 2024. Ali described accounts from the book that highlight Trump's possible fixation on the "Will & Grace" actor, such as Trump mentioning Messing often during interviews with Setoodeh without being asked. In one excerpt from an interview, Trump recounted a time when Messing supposedly thanked him profusely. Setoodeh wrote: "'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.'"
Trump went on to describe "The Apprentice" as a "lead-in" for "Will & Grace," raising the sitcom's ratings. When Setoodeh said "The Apprentice" couldn't have been a lead-in for "Will & Grace" since the sitcom aired earlier, Trump corrected the phrasing: "'A lead-in — or a lead-out,' he clarifies."
Trump told Setoodeh about his crush on Messing
In the first "Apprentice in Wonderland" excerpt shared on Yashar Ali's Substack, Donald Trump seemed to imply Debra Messing might have had a crush on him back in the day. Ali qualified the excerpts by saying Trump isn't usually truthful. (Remember when Trump posed as his own publicist?)
In the second excerpt from Ramin Setoodeh's book, Trump mentioned Messing again and was adamant she was grateful before becoming a critic. Then, Trump said he once had a crush on Messing: "'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.'" Setoodeh wrote that Trump encouraged him to include the accounts of Messing in the book.
Messing has shared her negative feelings on Trump. In 2019, she and Eric McCormack (also from "Will & Grace") both retweeted a tweet on X, formerly known as Twitter, from The Hollywood Reporter. The outlet's seemingly deleted article mentioned how Trump would be in California for a fundraiser. In Messing's since-removed retweet, she said: "Please print a list of all attendees please. The public has a right to know" (via People). Trump told Setoodeh he'd kept an eye on Messing's X account while he was president. Sure enough, he had something to say about her tweet.
Some of Messing's tweets caused backlash
After Debra Messing's tweet about his 2019 fundraiser, Donald Trump tweeted his reported encounter with the once-thankful Messing and quipped, "How times have changed!" She tweeted back to encourage Trump to discuss current events instead (via Vulture). Days later, Trump tweeted: "Bad 'actress' Debra The Mess Messing is in hot water. She wants to create a 'Blacklist' of Trump supporters, & is being accused of McCarthyism." He also mentioned accusations of racism Messing received.
According to Deadline, Messing liked a picture on social media of a church sign calling Black supporters of Trump "mentally ill," which Trump compared to one of Roseanne Barr's controversies on X. Messing later apologized but voiced her opinion on how Trump and conservatives didn't have the best interests at heart for Black voters.
Messing received backlash again in December 2020 when she tweeted Trump, hurling insults such as "inept" and "narcissistic" before adding, "I hope you live a long life in prison where you become the most popular boyfriend to the all inmates" (via the Independent). When conservative news site The Daily Wire criticized her for homophobia, Messing said she wasn't trying to be anti-LGBTQ+ but that Trump had hurt many people: "My hope is (and this is the first time in my life) that the tables are turned and he is the victim of perpetrators. #LGBTQIAally." After that, it's surprising Trump spoke so much about Messing in his "Apprentice in Wonderland" interviews.