Writing in a New York Times column on Nov. 3, 2008, Kristol laid out a possible path for a McCain upset: "But what if John McCain pulls off an upset...It’s possible. What if the polls, for various reasons, are overstating Obama’s support by a couple points? And what if the late deciders break overwhelmingly against Obama, as they did in the Democratic primaries? McCain could then thread the Electoral College needle."
Kristol didn't exactly predict a McCain victory. He added that pulling it off would be "an inside straight," but said, "But I’ve seen gamblers draw them."