Trump: Why My Crush on ‘Quite Attractive’ Debra Messing Turned to Hate

Jabin Botsford/The Washington Post via Getty
Jabin Botsford/The Washington Post via Getty

First things first: In Apprentice in Wonderland, by Ramin Setoodeh, Donald Trump himself brings up and discusses the long-rumored hot-mic tape from NBC’s The Apprentice in which he is supposedly heard to say the n-word. But he does so only to strenuously deny it exists.

More of that in a moment. First: news of a surprising crush Trump appears to have nurtured for years which has now, inevitably, turned sour.

Debra Messing walks a red carpet.

Debra Messing seen during 2005/2006 NBC UpFront arrivals at Radio City Music Hall in New York City.

Jim Spellman/WireImage via Getty Images

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Setoodeh, co-editor-in-chief of Variety, examines Trump’s rise to TV fame via The Apprentice and The Celebrity Apprentice, prior to his entry into politics and capture of the Republican Party, the White House, and the national story.

Interviews for the book were carried out from 2021, when Trump was fresh out of power, seemingly never to return, to 2023, when his seizure of a third successive GOP nomination was coming to appear inevitable.

Of course, Trump rants to Setoodeh about his political enemies. Unsurprisingly, Anthony Fauci, the scientist who became the public face of the fight against COVID-19, is prominent among them. “Fauci was wrong on everything,” Trump rants—after Setoodeh turned up to an interview wearing a mask.

Fauci’s own book, also out Tuesday, contains withering portraits of Trump. But as Setoodeh is chiefly concerned with Trump as a celebrity, it’s celebrities other than Trump that take up most of his time.

Trump dings the likes of Caitlyn Jenner and Khloe Kardashian, rather soft targets for someone who claims his “macho swagger” reminds people of Clint Eastwood. (Jenner is now a high-profile supporter, making the next Mar-a-Lago encounter likely to be awkward.) But aside from the Kardashian clan, there’s another surprising celebrity who gets Dirty Harry worked up: Debra Messing, at the time of The Apprentice another of NBC’s biggest stars.

“Trump brings up Messing again,” Setoodeh writes about the actor’s encounters with Trump during his TV years, then her emergence as a critic after his turn to politics.

Debra Messing walks a red carpet.

Debra Messing at a Paley Musuem event in 2023.

Cindy Ord/NBCUniversal via Getty Images

“He confirms something that he’d only dropped hints about in our last meeting. 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. ‘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.’”

If I Did It: Trump on That Tape

Despite denying the existence of the Holy Grail for his opponents—the supposed hot-mic n-word tape—Trump can’t help but tackle the subject head-on and offer an O.J. Simpson-style “If I did it” version of events.

“Trump takes a short pause,” writes Setoodeh, while recounting the tale of Omarosa Manigault, the Apprentice villain who became a White House aide and who says she’s heard the tape.

“By the way,” Trump says, “there are no tapes!”

“I was wondering how I’d bring this up,” Setoodeh writes, “but I guess I shouldn’t have been surprised that Trump—often eager to discuss all the scandals associated with him—would just blurt it out.”

Trump blurts out a lot. Often, Setoodeh prompts him by playing clips of The Apprentice and The Celebrity Apprentice, prompting a torrent of braggadocious-yet-wistful memories from the Norma Desmond of U.S. politics in which Trump reveals, for one thing, that he doesn’t know how TV ratings work.

Setoodeh writes, “By now, the whole world knows about the Apprentice tapes, an ugly rumor that has followed Trump like his own Watergate.” But Trump denies that outtakes are being held by Mark Burnett, the show’s British-born creator.

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“‘They say it’s guarded,’ Trump says. “It’s not guarded. It doesn’t exist. It would have come out 15 different ways. No. 1, it’s a word that I’ve never used. I’ve never used it in my life!”

Trump, however, “can’t resist a thought experiment where he might have said the word but never while being recorded. ‘Would I use it when the mics are all hot? The mics were always hot. Because, a lot of times, they would see stuff during a break that was good. They’d use stuff during the breaks, which was my idea.’”

Like so many authors of books about Trump in politics—from tell-alls to deep reportage and back again—Setoodeh seeks to divine how Trump ticks.

“As Trump attempts to dismantle this story that has followed him for years, he still finds time to pat himself on the back. ‘Yeah, because a lot of good stuff comes out,’ he says, boasting about his improvisation skills. ‘Frankly, better stuff comes when they don’t know it’s on,’ he says about his interactions with the contestants.

“Trump seems to have forgotten that my two tape recorders are running, or that we’re speaking about the breadth of his career, culminating in his presidency. He just wants me to understand how he made great TV.

“The orange skin around his eyes crinkles. He’s back in defense mode… ‘It’s so ridiculous. It never existed, and if it did exist, it would have been exposed years ago. You don’t think during a presidential campaign that tape would have been released. Right? That says it better than anything, if you think about it.”

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Setoodeh records a startling tale about a contestant who earned “extra facetime with Trump,” an experience that “could be valuable [but] could also be draining—and occasionally disturbing.”

“After a task with the Home Depot—during which the contestants were supposed to create a customized experience for shoppers—the Apprentice house was abuzz about what Trump had supposedly said to Erin Elmore, a 26-year-old attorney from Philadelphia, in the boardroom.

“On the episode, she’s seen flirting with Trump, even winking at him before she gets the boot. But at some point, Trump allegedly boasted to her, ‘I’ll show you my nine-inch power tool,’ as she pleaded ignorance about her knowledge of home repair. (No one knows for certain whether Trump was wearing a microphone when he made that lewd joke or if a recording exists.)

“Trump didn’t get in trouble for it. Indeed, since the moment didn’t make it to air, it might as well never have happened. ‘There’s no truth to it,’ says Elmore, a Republican strategist who worked as a surrogate for Trump’s 2016 presidential campaign. ‘It’s kind of hearsay.’”

Trump Seemed to Think He Still Had Presidential Things to Do

“Suddenly, in the midst of talking about [Joan] Rivers,” a Celebrity Apprentice contestant, “Trump careen[ed] off course.

“‘I have to get back up,’ he says, pointing to his office, ‘because, you know, I’m doing the whole thing with the Afghanistan.’ It’s not clear if he’s talking about conducting another interview, or if he’s momentarily forgotten that President Joe Biden has barred him from receiving the customary ex-presidential intelligence briefings. Biden remains on Trump’s mind. ‘Has he blown the Afghanistan?’ Trump asks.”

Donald Trump gestures on 'Celebrity Apprentice'

Donald Trump during the Celebrity Apprentice live season finale on May 16, 2010.

Bill Tompkins/Getty Images

Setoodeh says he “told Trump that I wasn’t there to talk politics today; in our last conversations, he’d spent so much time ranting about how he won the 2020 election that I just needed him to focus on analyzing the show that engineered his rise. But he can’t help himself.

“Trump tells me that if he’d been in charge, the chaotic withdrawal from Afghanistan would have gone a lot differently. ‘I wanted to get out too,’ Trump says. ‘Actually, the Taliban, who I dealt with, was not living up to certain things. But they were getting ready to live up to them.’ It’s strange, but not surprising, to hear Trump suddenly talking about the Taliban like a bad contestant on The Apprentice he’s about to fire.”

Trump Thinks He Could’ve Beaten Obama

In 2011, NBC persuaded Trump to drop a flirtation with running for the GOP nomination against Barack Obama, the subject of the racist “birther” conspiracy Trump did much to promote.

“The first time”—meaning 2008—“would have been hard,” Trump says. “The second time was easy because he was a failed president. He was four years in, and the country was doing poorly. I think it would have been easier than beating Hillary Clinton.”

For what it’s worth, Trump calls Mitt Romney, the Republican nominee in 2012, “a total asshole” and “a real schmuck.”

Trump also says Mark Burnett tried to stop him running in 2015, saying NBC would give him “any money you want.” Trump went into politics anyway. Burnett voted for Hillary. Trump tried to have Ivanka replace him as host of The Apprentice with her brothers Don Jr. and Eric in as judges. NBC didn’t buy it.

Trump Was Fed Lines in The Apprentice Boardroom

Trump’s reliance on scripts or autocues, or not, and the efficacy of his off-piste rants, remains a theme of debate. One Apprentice contestant, Clay Aiken, tells Setoodeh the boardroom monologues that stoked Trump’s rise as a supposed improvisatory genius were in fact anything but.

“A small device that sat on the table in front of him. On TV, it looks like a telephone. ‘It’s essentially a screen, where they could type him messages, and send him messages from backstage.”

Trump Gave an Interview the Day His Sister Died

In November 2023, Setoodeh went to Mar-a-Lago. Trump’s older sister, Maryanne Trump Barry, a federal judge, had died that morning, aged 86. In New York, furthermore, Donald Trump Jr. was on the stand in the civil fraud trial that would cost the family billions.

“So I’m a little surprised when his office emails me to say he’ll need to push back our interview by only an hour,” Setoodeh writes.

“As he settles into his seat, I offer my condolences about his sister. ‘Awww, thank you very much,’ Trump says. ‘I just found out this morning. It’s too bad. She was a good woman, actually. Very smart. Very, very smart. Anyway, so good.’

“Trump—who once described himself as “nostalgic” watching old clips of The Apprentice—isn’t feeling sentimental about Maryanne’s passing.”

Trump also tells Setoodeh “they just finished up the trial” in New York, and ‘We won everything.” They did not. For the judge, Arthur Engoron, Trump has characteristic abuse: “He’s crazy. He’s a fucking lunatic.”

“Trump’s storytelling is stuck on the same track,” Setoodeh says. “But it’s a storytelling track that millions seem to love.”

Trump Can’t Believe His Own Story

Setoodeh asks Trump about “the Alice in Wonderland reference in Rage,” Bob Woodward’s second Trump book, which inspires Setoodeh’s own title.

The Washington Post veteran “reports that [son-in-law and adviser] Jared Kushner believed the secret to unlocking Trump is seeing him as a real-life Cheshire Cat—that Trump is always appearing and disappearing, confusing people for the sake of confusion.

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“‘I don’t know what he means by that,’ Trump says. ‘You’d have to ask him.’

“Fair enough. But does he know the story of Alice in Wonderland?

“‘Well,’ Trump says. ‘It [his presidency] was like a fairy tale.’ He repeats it with more conviction. ‘Look! It was a fairy tale. The first night in the White House, I end up standing outside the Lincoln Bedroom. It’s so iconic. I call people. I said, “I’m standing in the Lincoln Bedroom right now.” He had pictures of his son who died—it’s tragic. But it was Lincoln. What can I do? It was like,’ Trump tries to find the right word, ‘amazing.’

“Trump seems pleased with himself. ‘It takes you a while to get over it. It was a dream, yeah. There’s nothing like it.’

“It was a dream from which he has yet to wake up—and neither have any of us.”

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