The Biggest Loser: Why Donald Trump Couldn’t Hack It in Hollywood

Donald Trump spent years trying to make it as a Hollywood mogul. Nobody bought his act

The Ponderosa” is what producers on Mark Burnett reality shows call the residence where eliminated contestants are exiled while taping of the competition continues. During the ill-fated Los Angeles season of The Apprentice in 2006, the Ponderosa was an unremarkable corporate apartment complex in Marina del Rey. While Donald Trump stayed for months at the Beverly Hills Hotel conducting various alleged affairs, his fired candidates were detained without their wallets or cellphones in a beachside condo to guarantee they wouldn’t leak the show’s plot. “When you want something, you have to tell the producers you want something from ‘Uncle Mark,’” said Jenn Hoffman, a cast member. “But all we ever needed was tequila and mahi-mahi, basically.”

You don’t generally think of Donald Trump when you think of L.A. Before he was president, the chief resident of Trump Tower’s penthouse cultivated his besuited image as the consummate New Yorker, even when he was at Mar-a-Lago eating prime rib and “beautiful” chocolate cake among the Sansabelt set.

But the truth is, Trump spent a lot of time in Los Angeles, much of it in a purgatory of his own making circa 2006 and 2007. He was allowed to keep his wallet, but The Apprentice franchise was near death. To his dismay, no subsequent season of the show enjoyed ratings that were as high as the first. For a few seasons after its January 2004 debut, The Apprentice had remained a valuable franchise, even when season 4 sank to a number 38 average ranking, with about 11 million weekly viewers in the first half of the 2005-06 season. With season 5’s plunge to 51st place, it was decided that the show would leave New York and head to Los Angeles.

Trump gamely made the most of the move, dining with Wolfgang Puck on the show, even taking off his socks and, grimacing, tottering in the Santa Monica sand in dress slacks and a blazer. Although beached, and finding himself in the same boat as his floundering former Apprentice candidates, Trump would do as he always seems to do—find his way out and up: a guy who turned a massive inheritance into a string of financial crises, with an indisputable record of infidelity and no formal political experience, somehow became a viable presidential candidate. And yet, I’ve come to wonder if, late at night in the executive residence amid ice cream pints, Twitter rants, and blaring TVs, Trump rues what might have been in Southern California had he played it differently.

Trump dreamed of becoming a Hollywood player. “The ultimate job for me would have been running MGM in the ’30s.”

During the depths of The Apprentice’s grim L.A. run, Trump would purchase a 5,400-square-foot Beverly Hills estate; 13 years and a presidential inauguration later, the Trump Organization unloaded the house to a billionaire Indonesian businessman for $13.5 million, far more than the $8.3 million value appraised by Los Angeles County in 2018 and about double what Trump paid for it. At first blush, the transaction appeared to Trump-skeptical reporters as an affirming story of corruption. Local real estate experts are not so sure. “Based on the square footage of the house, it was a little on the rich side,” Luis Pezzini, a Beverly Hills realtor told me. “But it’s a 29,000-square-foot lot. Could it command 13.5? Of course.”

Profitable as it was, the sale of the mansion marked the official demise of Donald Trump’s longtime dream to become a Hollywood macher. As a young man, Trump had been interested in attending film school at USC. “I’ve always thought that Louis B. Mayer led the ultimate life, that Flo Ziegfeld led the ultimate life, that men like Darryl Zanuck and Harry Cohn did some creative and beautiful things,” he told Playboy in 1990. “The ultimate job for me would have been running MGM in the ’30s and ’40s—pretelevision.”

Maybe that’s the tragedy of Trump. Though he reportedly learned his straight-to-camera scowl by studying Clint Eastwood’s Dirty Harry, and his appetites and parental bankroll were well suited for louche movie moguldom in the pre-#MeToo era, Trump ultimately decided to take a safer path. He gave up on USC to major in business at the University of Pennsylvania before going to work for his father, Fred, at the family’s real estate company. When President Trump unleashed a stream of puerile insults west, telling reporters “Hollywood is racist … really terrible,” it can be heard as the tirade of a frustrated inner child, stomping on the sandcastle built by a clique of cooler kids who spurned him. But, until recently, Trump’s interest in the entertainment business was undiminished.

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Trump with The Apprentice creator Mark Burnett

Before The Apprentice took off, Trump had been making cameos on sitcoms for years, including Brooke Shields’s Suddenly Susan, The Fresh Prince of Bel-Air with Will Smith, and Fran Drescher’s The Nanny. But when Trump tried his luck in L.A. in a bigger way, he became at best a bit player—reality show fame is rarely real Hollywood power unless, as Ryan Seacrest demonstrated, it’s played just right.

“No one cared about Donald Trump in Hollywood,” said Susan Winston, who produced the broadcasts of nine Trump-owned beauty pageants. “He was nothing. He didn’t mean anything. There were people in Hollywood who had much more power, much more money.”
Jeff Klein, owner of Tower Bar, the go-to industry dining room at the Sunset Tower Hotel, quickly recognized where Trump belonged in the Hollywood pecking order. When regular Steven Mnuchin, then running a bank in Pasadena, brought Trump in around 2010 or 2011, Klein recalled, “They demanded a prominent table, the one everyone can see as you come in. It’s not where real movie stars sit. It’s where WB stars go—table 25. I remember him saying hello to people he didn’t know—Brian Grazer or someone like that. He reminded me of Lisa Vanderpump.”

Earning comparison to a star of The Real Housewives of Beverly Hills is not playing it just right. Nor are the grubby, exploitative shows Trump produced after announcing in 2006 that he was creating a production company to be run by season 2 Apprentice loser Andy Dean Litinsky. Trump might have had more success if he’d just hung a shingle in Chatsworth and fashioned himself after Burt Reynolds’s porn producer in Boogie Nights.
A partnership among Trump, the veteran producer RJ Cutler, and Hasbro to pitch a TV version of Monopoly fizzled. During their three-year run, Trump and Litinsky delivered The Girls of Hedsor Hall, a reality show about wayward young women; Donald J. Trump Presents: The Ultimate Merger, in which Omarosa Manigault starred as the prize for whom bachelors vied; and Pageant Place, chronicling the lives of three New York City roommates: a Miss Universe, a Miss USA, and a Miss Teen USA. (Also involved in Pageant Place was now-jailed Trump attorney Michael Cohen, who helped pitch the show to VH1, according to Michael Hirschorn, the channel’s former executive VP of original programming.)

As much as Trump may have longed for moguldom, getting into that position required a level of maneuvering he never committed to and might not have pulled off. With lots of help from his powerful father, he got Trump Tower built in the ’80s and lent his name to many other developments of steadily diminishing prominence, but in Hollywood, you’re only as good as your last show. Trump’s mastery of the gossip press and the balls-out selling of his persona and brand managed to make him a caricature king in New York, but his bridge-burning style didn’t fly in Hollywood, where professional relationships are nurtured over decades, and stiffing your business associates is an infamia. Winston got a view of how Trump operates when he demanded screen credit as a producer even though he was not a host of the Miss Universe pageants and barely participated in their production.
“He’d show up the day of the pageant. He insisted we make sure he was seen on camera three times,” Winston said. “He would come in, and I would make him shake my hand. I was torturing him. I knew he didn’t like to touch people. I’m the executive producer of this TV show sharing the marquee with him, and the guy is going to brush past me? I don’t think so.” Soon after he bought it, Winston said, Trump moved the Miss Universe offices out of comfortable accommodations in Century City “to a place somewhere in Hollywood that sold rugs and we had to go up three flights of stairs.”

It wasn’t even Trump who got The Apprentice made. It was someone with real Hollywood power. Coming off the success of Survivor, Mark Burnett and his development lieutenant Conrad Riggs had honed an idea for a business reality show. Trump’s relentless campaign to bully New York tabloids to refer to him as a billionaire—even as his real-life businesses were foundering—suddenly started paying dividends. “Pre–The Apprentice, he was Donald Trump doing Pizza Hut commercials, who had gone bankrupt seven years earlier,” said ad executive and TV host Donny Deutsch.

“No one cared about Donald Trump in Hollywood. He was nothing. There were people in Hollywood who had much more power and money.”

Although Trump was Burnett’s first choice for The Apprentice, the producers explored other possibilities. “I met with Jack Welch,” Riggs said, “but he seemed to have moved on with his life and didn’t want to make the time commitment. I talked with Richard Branson’s team, and we could have pursued that if Trump wasn’t an option. … I talked to people who worked with Warren Buffet, but it never got to a meeting with him.”

As evidence of what real power in Hollywood means, consider that at least two years before Burnett and Riggs started developing The Apprentice, Mark Bethea, an Air Force veteran trying to break into the reality TV business, had an idea for a reality show called C.E.O. He had two possible stars in mind, Lee Iacocca, the former chairman of Chrysler, and Trump. The idea was almost identical to what The Apprentice would be years later. Bethea registered a five-page treatment with the Writers Guild of America on August 30, 2000. Bethea pitched C.E.O. to Riggs in 2001; The Apprentice debuted in 2004. Riggs and Burnett contend that The Apprentice idea came fresh from Burnett. In the litigation that followed, during which future Trump adversary and now-troubled lawyer Michael Avenatti was tangentially involved in Bethea’s camp, Burnett and Riggs paid Bethea an undisclosed amount in an out-of-court settlement.

“When you think about Hollywood moguls, a lot of them are killers like David Geffen, [Jeffrey] Katzenberg, [Barry] Diller,” Klein said. “I don’t think [Trump] could have been a mogul. Hollywood is like high school—they would have made fun of him. Moguls are smart and conniving, and when it comes down to the business, they don’t fuck around.” It’s a fitting metaphor for Trump’s Hollywood ambitions that his star on Hollywood Boulevard was repeatedly attacked by vandals after he took office as president.

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Trump’s star on the Walk of Fame was obliterated by a vandal in July 2018.

Gabriel Olsen/Getty Images

Trump has always been obsessed with celebrities. The closets and walls of his New York offices are stuffed with autographed photos and memorabilia. He understands that there’s power in who you know and what you can get them to do for you. When Bill Royce, an Emmy-winning producer with The Tonight Show with Jay Leno, was hired to book talent for the Miss Universe pageant broadcasts, he met with Trump at his Century City offices. “He said, ‘So tell me who’s the biggest star you’ve ever booked?’ I said, ‘Well, it was Harrison Ford or maybe Robert De Niro,’” Royce recalled. “He said, ‘Oh, that’s pretty big. Tell me, who’s the smallest star you ever booked?’ I said ‘Billy Barty, the dwarf.’”

In 2002, the same year Trump bought a troubled golf course in Palos Verdes, he made a deal to start Trump World, a Robb Report-style magazine aimed at chronicling the finer things. L.A. was to be a key part of Trump World. “Every hot restaurant that opened out here I wrote about,” recalled Carol Dickson, the magazine’s L.A.-based food and travel editor. “I wrote a story about where to find the best caviar, centered around Petrossian in West Hollywood.”

When the magazine folded in 2006, Dickson said she was stiffed out of payment for her final two articles, about $2,000. She wrote to the Trump Organization, “[and] about a month later, I got a letter from his assistant saying Mr. Trump had nothing to do with the magazine, which is hysterical because he was on every cover.”

In the 1980s and 1990s, Trump pursued a spate of high-profile Southern California projects, including building a tower on the site of the old Ambassador Hotel; taking over the San Diego Padres; and trying to buy his favorite place to stay in town, the Beverly Hills Hotel. None panned out. The Access Hollywood-Billy Bush “Grab them by the pussy” tape that surfaced a few weeks before the 2016 election was recorded in September 2005 in a parking lot at NBC Studios, where Trump, always looking to sustain his pseudo stardom, was to appear in an episode of Days of Our Lives.

The Apprentice: Los Angeles portrayed Trump as traveling by chauffeured limo and living in “his” mansion next door to the one where the week’s winning team slept in bedrooms and the losers roughed it in tents on the lawn. Actually, the mansion on the show was rented and in the hills near Mulholland Drive between Benedict and Coldwater canyons, according to producer Jonathan Braun. Trump wouldn’t buy his house in the flats of Beverly Hills until the following year and was staying at the Beverly Hills Hotel. In June Trump was taping a golf reality show called The Big Break in Palos Verdes by day and The Apprentice at night. He drove himself the 35 miles back and forth in a “nice Lexus, black,” said Denny Hepler, who went on to win the golf show competition. Melania Trump had given birth to the couple’s son, Barron, in March 2006, and after appearing on the show’s premiere episode, she was not seen on set again, leaving Donald to his ways.

Trump was interested in women both on the golf course—once asking Hepler “if he should sponsor one or two of the girls”—and off. It would be about three years later that Trump walked up to an attractive woman at BOA Steakhouse in West Hollywood, looked her up and down, and introduced himself. Her date that night, who in a bizarre coincidence turned out to be Michael Avenatti, was at the bar getting her a sauvignon blanc. Trump didn’t know him yet, but when Avenatti returned, Trump knew he was blocked. “He clearly figured out that I was with her; [he] introduced himself; I introduced myself. We shook hands, and then he turned around and left,” Avenatti recalled. His date joked that Trump’s gaze left her “feeling like a piece of meat hanging from the rafters,” Avenatti said.

Hugh Hefner embodied the lifestyle and business acumen that Trump clumsily emulated, and his sorties to the Playboy Mansion during his L.A. years highlighted the differences between the two men. Hefner remained a force in L.A. for generations, not least because he exhibited personal charm and occasional tact. “The mansion wasn’t a bordello,” said Braun, who produced the episode of The Apprentice shot there. “You couldn’t just choose a girl and go have sex with her. There was a leering, sneering lasciviousness to Donald Trump when he would view the women who were there. Hef looked at the women as people, and Donald Trump did not.”

What Trump would leverage from The Apprentice was primarily not Hollywood power but political might. At dinner with Puck, at Spago with the cameras off, Trump asked the chef and some Apprentice candidates, “‘What do you think? Should I run? Would I be a good president?’” cast member Hoffman recalled. “And, of course, everyone’s like a bobblehead: ‘Uh-huh, uh-huh, yeah.’” (A Puck spokesperson said the chef has no recollection of the dinner.

Further evidence of Trump’s long game can be seen in episode 5 of The Apprentice: L.A., when he travels to deliver a speech in Minnesota. In the front row is a man holding up a small sign—this is 2006—TRUMP FOR PRESIDENT. Trump was planting seeds. Product placement on the show cost up to $1.5 million for advertisers, but for Trump, who split those revenues with Burnett, it was free. In case you thought the first flash was by chance, a minute later appears a full-frame close-up: TRUMP FOR PRESIDENT.

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Donald Trump eats an ice cream bar at a Lakers game in 2005

AP Photo/Mark J. Terrill

Politics was truthfully a better fit for what Trump had become. The persona that had made him a star wasn’t that of an L.A. guy. His image, cultivated as carefully as Hulk Hogan’s handlebar mustache, is of a bombastic businessman in a big suit with a red tie living in a tower. When Trump had to remove his shoes and socks for the beach shoot on The Apprentice, he was out of character and insecure about his freckled calves and unsure stride in the sand. “He’s balancing kind of awkwardly,” Hoffman recalled, “then he notices that we’re watching him, and he says almost bashfully, ‘You can tell I’m not a beach guy.’”
But seated for a fashion show on the sand and watching shirtless male models strut around him, Trump seemed to be channeling his childhood preacher Norman Vincent Peale, the author of The Power of Positive Thinking. Trump is heard saying, “I have a great body. I really do. I have a great, great body. I could wear that suit.”

After season 6’s disappointing ratings, NBC entertainment chief Kevin Reilly canceled the series but soon left the job. Reilly’s replacement, Ben Silverman, ordered two more seasons of The Apprentice, but with a format change: celebrities playing for charity. He also insisted that NBC start taking a share of product-placement revenue. Back in New York, viewership improved, and it ran for seven more seasons with Trump as host.

Justin McConney, Trump’s social-media assistant in the years before the White House, tried to convince his boss to pitch a talk show. Trump refused, saying, “‘You don’t know the amount of time that goes into it, and the questions you have to ask people, the research, and the topics,’” McConney recalled. “The Apprentice was a very fast thing for him to film. It was in his building. It was on his schedule. The Saturday episodes, there were a lot of times where they were supposed to film the boardrooms at like 2 p.m., but Trump would be out at Bedminster golfing.”

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After the election, Trump sold his Beverly Hills mansion for $13.5 million. He purchased the home during The Apprentice’s troubled L.A. run but preferred to stay at the Beverly Hills Hotel

The Beverly Hills mansion was never Trump’s Xanadu. He once told Travel + Leisure that he preferred to stay at the Beverly Hills Hotel “because the hotel has everything I could possibly need.” Michael Wolff, author of the Trump-eviscerating Fire and Fury and Siege, once interviewed Trump at the mansion and recalls that “it seemed uninhabited, with cast-off hotel furniture. Large unappetizing pieces, beige-y brownish. Kitchen where a meal has never been prepared. Nobody gave it more than a perfunctory thought.”

When NBC canceled The Apprentice following Trump’s escalator announcement of his candidacy in June 2015, he threw a fit. “Boy, boy, boy, you did not want to be around him then,” campaign aide Sam Nunberg recalled. Added McConney: “Once The Apprentice was done, he took the chair from the show and moved it up into his office and put a sign on it that says, ‘The chair from The Apprentice. 2004 to 2015. #1 Show.’”

If Trump seeks a late-life grab for relevance as a Hollywood power player, he could still decide to move to L.A. when his time in D.C., or in confinement, is done. His challenges include the fact that in the 2016 election 68.4 percent of California voters did not vote for him. But if he oversees an economic downturn that tanks the Southern California real estate market, he might be able to buy something nicer in 2021 or 2025 than his old mansion and at a discount. He’d need to take a diction lesson first—Trump can’t say the word “film.” “He joked about it once,” producer Braun said. “He says ‘fill-im.’ He said, ‘I can’t say that word. I just can’t say it. It doesn’t come out.’”

Trump knows films, though, like Citizen Kane, the story of a man who had everything but in the end yearned only for the lost pleasure of a childhood day aboard a sled named Rosebud. “The word ‘Rosebud’ is maybe the most significant word in film,” Trump once said for a never-completed project in which documentarian Errol Morris interviewed notables about their favorite movies. “The wealth, the sorrow, the unhappiness, the happiness just struck lots of different notes,” Trump continued. “Citizen Kane was really about accumulation, and at the end of the accumulation you see what happens, and it’s not necessarily all positive, not positive.”


Allen Salkin is coauthor of The Method to the Madness: Donald Trump’s Ascent as Told by Those Who Were Hired, Fired, Inspired—and Inaugurated (Macmillan).

RELATED: A Brief History of Donald Trump’s L.A. Fails

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