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

From a failed attempt to buy the Beverly Hills Hotel in the ’80s to his recent jabs at the industry Trump has made a long tradition of doing the wrong thing

Between 2006 and 2007, Trump lived in a purgatory of his own making in Los Angeles, but his troubled history with the city—and with Hollywood in particular—goes back to the ’80s and continues through today. Here are some greatest (or, rather, worst) hits.


Takes an interest in the Beverly Hills Hotel and announces he’s hiring Steve Rubell and Ian Schrager, creators of Studio 54, to run it. Trump’s efforts to lowball the owners of the landmark fail miserably. “He was never a serious contender,” one of the owners says.


Proposes building a world-record-setting 125-story skyscraper over the site of the Ambassador Hotel after joining a syndicate that bought the 23.5-acre lot for $64 million. The Los Angeles Unified School District counters that it needs the land for a new campus. Trump later says the district is taking the land from him “as viciously as in Nazi Germany.”


Pitches a TV special, Donald Trump Presents the Most Beautiful Women in the World, to ABC president Roone Arledge, boasting: “I’ll bet it gets one of the top five highest ratings of the year!” The show does not make it past the pitch stage.


Proposes Grand Avenue project for a residential and commercial development to revitalize downtown L.A. but is ditched in favor of a team lead by architect Frank Gehry

donald trump hollywood failure
Donald Trump
at Universal Studios in 2004.


Complains The Apprentice was “screwed out of an Emmy” at the 56th TV awards show by The Amazing Race, a show he dismisses as a “piece of crap.”


Donates $10,000 to Arnold Schwarzenegger to help him pay his campaign debt after appearing on The Apprentice. Trump later proclaims Schwarzenegger “Dead,” and Arnold fires back: “I’m still here. Want to compare tax returns?”


Offers to buy the Beverly Hills mansion of Johnny Carson sidekick Ed McMahon, who is ailing, and promises to allow McMahon to stay in the residence. McMahon politely declines the offer.


Strips Carrie Prejean of her Miss California crown, insisting his decision has nothing to with Prejean’s anti-gay-marriage comments or seminude photos, instead attributing it to Prejean’s refusal to appear on Larry King Live and at the red-carpet events.


Is semiofficially barred from the Grove when owner-developer Rick Caruso tells a TMZ photographer that he would “be happy to” ban Trump from Caruso’s flagship L.A. shopping complex.


Claims California causes wildfires by not raking fallen forest leaves, a fire-prevention technique he says he learned about from the prime minister of Finland, who denies discussing leaf raking with Trump.


Insults the industry that spurned him: “Hollywood is terrible. You want to talk about racists? They’re racists. People call them the elites, but they’re not the elites. They go after the elites.”

RELATED: Donald Trump Tried to Make a Go of It in Hollywood. He Failed Miserably

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