LATE NIGHT WITH THE DONALD
Trump has been campaigning for decades on Leno and Letterman
No one has made more bonehead statements in this presidential run than Donald Trump. Pundits sometimes attribute this to inexperience. They’re wrong.
Trump has been crafting his campaign since at least 1980, when Rona Barrett asked him whether he’d ever seek the nation’s top job. Why would a gossip columnist pose such a question? Maybe Trump planted the idea?
In 1988, he assured Oprah Winfrey that if he ever sought the presidency, he’d probably win. Then in 1999, Trump formed a presidential exploratory committee on the Reform ticket. His first primary would be in California, where he made his pitch on Jay Leno’s Tonight Show.
As a producer for the show, I booked and worked directly on Trump’s appearances, and I’ll never forget that one. Leno introduced Trump as “the next president of the United States,” and he walked out to the strains of Hail
to the Chief while flashing victory signs. Leno was going for a joke. Trump was serious.
The real estate mogul went on to win the Golden State Reform Party primary in 2000, but soon dropped out of the race when it became apparent he had no chance of winning the presidency. He has never liked losing.
DRY RUNS ON TV Trump would return to The To
night Show in 2004, ostensibly to plug his new NBC show, The Ap
prentice. But Trump went out of his way to push his political views. And it didn’t stop there.
During subsequent bookings on both NBC with Leno and CBS with David Letterman, Trump hinted at his interest in a presidential bid. I thought he was doing it as a ruse to promote The
Apprentice and later Celebrity Apprentice; I chalked it up to unconventional but effective marketing.
But now that he is the presumptive Republican presidential nominee, I realize I had it backward: Trump wasn’t posing as a presidential candidate to boost his Nielsen ratings. He was actually making a campaign dry run under the guise of being a celebrity. I’ve reviewed Trump’s interviews with Leno and Letterman over the years, and discovered he had regular talking points:
OPEC is ripping off our country with high gas prices despite huge oil reserves.
China is doing a number on us with unfair trade practices.
We’re spending billions to build the infrastructure of Iraq but nothing to rebuild our cities.
We need to bring back jobs to America.
Sound familiar? Trump has been honing his campaign shtick for more than 30 years, like a comedian testing material to come up with a killer set.
And he has made clear he sees late-night shows as integral to a campaign — for instance, comparing Mitt Romney unfavorably to President Obama in 2012 because "Obama, say what you want, he was on Jay Leno, he was on David Letterman. "
Is Trump a monster, as his critics contend? I don’t think so. Now, I don’t claim to be an insider. But I had a 10-year relationship with Trump and my phone calls were always returned, sometimes by him.
Backstage at The Tonight Show, he was always pleasant and never asked for special treatment. His wife, Melania, and his adult children were equally gracious. People who worked for him, including women, were loyal and supportive.
CAPABLE OF CHANGE Is he racist? In my experience, no. I’ve read his books, The Art of the Deal and The Art of the Comeback, and I think they reflect his business philosophy: Make outrageous demands, and then back off and negotiate a deal.
Does he have flaws? Yes, he has a bad case of inflated self-esteem, which severely clouds his vision. Just before a scheduled chat with Leno in September 2005, Trump greeted me by saying, “I’m here to save your sorry network.” Then he pointed out that The
Apprentice was rated No. 1. Except it wasn’t. The ratings had started to slip at the time. I thought he was joking, so I laughed. But he didn’t, and neither did his staffers. It was obvious that they hadn’t told him about his dropping Nielsen numbers. You can’t be president if you only hire yes-people.
Trump’s biggest problem? A tendency to be small and petty. He loved gossiping about people like Rosie O’Donnell with Leno and other hosts. This is a serious character flaw.
Is Trump capable of changing? I think so. He took direction from executives at The Apprentice by adding famous people and renaming it Celebrity Apprentice, averting a possible cancellation. Recently, he has used teleprompters to make major campaign speeches and toned down at least some of his bonehead remarks.
That’s huuuuuge.
Dave Berg is author of Behind the Curtain: An Insider’s View of Jay Leno’s Tonight Show.