Letterman Had Trump’s Presidency All Figured Out Back in 1999

While poking around for vintage David Letterman videos to illustrate my review of the new book Letterman: The Last Giant of Late Night earlier this week, I came across this. It’s from 1999, Dave’s Top 10 list of “Donald Trump’s Campaign Slogans.” “Huh?” you say. Well, in 1999 Trump began an exploratory effort to become the presidential candidate for the Reform Party. He announced it, of course, on television — not descending the Trump Tower escalator as he did in 2015, but during an appearance on CNN’s Larry King Live.

Trump employed longtime and still-active weasel Roger Stone as his campaign strategist, but Trump dropped out of the race after coming to the conclusion he could not win with a third-party candidacy. Not before winning the California and Michigan primaries, however — a specter of things to come. The list here is remarkably timely (“No. 10: He’ll make our national defense as impenetrable as his hair”) and the No. 1 answer is especially accurate and chilling.

These days, the retired Letterman has made it clear what he thinks of Trump, coming out of his old-man cave to declare our new president “a damaged human being” and “a person to be shunned.” By the way, that joke Dave makes in 1999 about Oprah Winfrey being his ideal vice-presidential running mate? Turns out, that wasn’t a joke, but truth once more: Trump told the press that Oprah would be his “ideal running mate.” Oprah for president in 2020 seems more realistic than ever…

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