...Trump’s oppo book was slim not because Clinton staffers had missed details regarding his divorces or corporate bankruptcies. It was short because they didn’t think he had much of a chance of winning the G.O.P. nomination.
Trump’s oppo book, however, did make 16 references to his 11-year tenure on The Apprentice, his reality-television program. It noted, in particular, footage of Trump telling one female contestant that “it must be a pretty picture, you dropping to your knees.” As staffers reviewed the file, one person familiar with the meeting told me, someone made an unusual suggestion: while this clip could be damaging, there might be far more impactful raw footage of Trump saying outlandish things that had ended up on the cutting-room floor. The person suggested that the campaign scour those outtakes for any such material, if it existed.
Another staffer present at the meeting argued that such a hunt would be a waste of resources and time. Money was better devoted elsewhere, such as looking at the possibility that Trump-branded clothing was made in China. The two started to debate if it was worth devoting resources to look for some tapes that no one was certain even existed. Then someone else in the room, who had ties to Hollywood, interjected that she had heard, anyway, that Trump “always stuck to his cue cards during the taping.” On that note, the suggested hunt for any potential outtakes was tabled—at least for the time being.
For more than a decade, between 2004 and 2015, Donald Trump sat in a leather chair pulled up to a long wooden table, as sleek as a bowling lane, more than 180 times. In a Brioni suit, with his cotton-candy hair, he climbed into the costume of himself and praised, berated, jostled, and bewitched his contestants on The Apprentice, inevitably ending the conversation with his trademark catchphrase, “You’re fired!” Viewers of the program adored, or at least found themselves amused by, Trump’s theatrics. But, for journalists, the Clinton campaign, and many people inside Hollywood, what Trump may have said between takes became a year-long fixation.
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Nevertheless, the Clinton campaign, which had seen Trump survive previous raucous scandals, refused to give up its own search. Two days before the election, one entertainment executive with ties to Clinton contacted someone in the industry who had said he had a copy of a tape depicting Trump that could create problems for the then candidate. Would this person be willing to pass him the footage to give to the Clinton campaign? Since the latest poll numbers indicated it was clear Clinton would win the election—likely in a landslide—this person didn’t want to risk it.
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As much as the tapes may have become a fixation for political operatives, journalists, and so many people in Hollywood, they may have also become a white whale during the campaign. Without the prospect of the tapes, maybe Clinton’s campaign would have arranged more rallies in the Rust Belt. News outlets may have focused more on understanding why so many Americans had stuck Trump-Pence signs on their lawns.
