Donald Trump’s Wild ‘Apprentice’ Behavior: Meltdowns on Set, a Shocking Nickname for an NBC Exec, an ‘Obsession’ with Debra Messing and More

William Earl
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Ramin Setoodeh’s new chronicle of Donald Trump and “The Apprentice” — titled “Apprentice in Wonderland” — has arrived in bookstores and is filled with juicy behind-the-scenes anecdotes from the former President’s long-running reality show. (Note: Setoodeh is the co-editor-in-chief of this publication).

Along with a fascinating narrative that shows how the NBC series led to Trump’s political career, as well as multiple new interviews between Trump and Setoodeh, there are countless details which add more context to the wild world of the reality juggernaut. See five of them below.

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Trump’s head-turning praise for Ben Silverman

Ben Silverman, then-co-chair of NBC Entertainment, recalls a particularly spirited talk with Trump in 2007.

“He thinks for a minute,” Silverman recalls of Trump. “And he goes, ‘I’m so glad a Jew is running the network again.’ And I said, ‘Woah! I could take that in two ways, but somehow coming from you, it’s a compliment.'”

Omarosa allegedly wanted to sleep with Piers Morgan for a “showmance“

“She is one of the most appalling human beings I ever met in my entire life,” Morgan says, claiming that Omarosa wanted to sleep with him — to put on a “showmance” for the viewers —  and then continued to falsely claim he was gay after he shut down her advances. “She would literally do anything if she felt it would keep her on the show and get ratings,” Morgan says.

Trump grew childlike while waiting to film scenes for “The Apprentice”

As time went on, he was finicky about having to wait at all on the set of “The Apprentice.” If he arrived and the cameras weren’t ready to shoot his scene, he’d storm off and return hours later, just to prove a point. To help track his whereabouts in real time, members of the show’s transportation team were instructed to trail Trump when he took his own car.

Easier said than done. As one driver explains, trying to follow Trump as he sped to his golf course at Briarcliff Manor was an occupational hazard. Trump would run red lights, stomping on the gas and leaving other cars in the dust.

Trump has an “obsession” with Debra Messing

Trump described meeting Messing one year at the NBC upfronts, in which he said she was fawning over him.

“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.” I point out to Trump that “Will & Grace” came on before “The Apprentice,” which would mean that it wouldn’t have received a ratings bump from viewers turning into “The Apprentice.” “A lead-in — or a lead out,” he clarifies.

“She was so thankful,” Trump says. “She said, ‘I can’t thank you enough.’ Do you believe this? I’ve been watching her. And I’m saying, ‘She’d do anything for me.'” As he makes this claim, Trump’s words are lathered with a suggestive grease, similar in tone to his boasting about women finding him irresistible in the leaked “Access Hollywood” tape.

…

The next time we talk, Trump brings up Messing again, and 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…”

Trump knew about the affair between his son, Donald Jr., and Aubrey O’Day — but hasn’t heard her pop song about it

The Danity Kane singer famously had a fling with Don Jr. when she was on the fifth season of “The Celebrity Apprentice,” which Trump admitted he was aware of.

When I ask Trump about O’Day’s affair with Don Jr., he takes a long pause. “I had heard that, actually,” he says, blinking. “No, I had heard that.” Did he know that O’Day had written a song about Don Jr.? “I hadn’t heard the song. But I had heard that,” Trump says, confirming once again that he’s aware of the story about Don Jr. sleeping with one of the contestants on “The Celebrity Apprentice.”

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