November 2016 – WASHINGTON – As election evening began in Midtown Manhattan, people who wanted Donald Trump to win — loyal Republicans who risked the scorn of conservative critics to work hard on Trump’s behalf — were not only not sure he would win, they were actively trying to imagine the best-case scenario for his defeat. But how could so many people get it wrong? So many people said Donald Trump would never be president. A host of people even laughed at the idea – though none are laughing now.
Let’s rewind the clock back to election night: At the Hilton Midtown, where Trump would hold his election-night event, a Republican strategist who had worked on the Dole campaign, two Bush campaigns, the McCain campaign and the Romney campaign had little confidence Trump would win, but felt sure he would exceed Romney. Even a close loss would have value, he explained, because it would likely force the Beltway Republicans who refused to help Trump to look into the mirror and ask whether they could have done more to elect a GOP president.
That’s the kind of thinking that was going on in the early evening of the most extraordinary election night in U.S. history. Trump supporters wanted Trump to win — that’s why they were there — but there were doubts galore. Even Jeff Sessions, the Alabama senator whose early endorsement was a huge boost for Trump, seemed unsure about a Trump victory. Sessions said that in the last few days he visited Trump county headquarters in Arizona and Virginia. He was struck by the intensity of the support there. “The feelings of the American public are legitimate, and the politicians need to hear it,” Sessions told me. “This isn’t going away. This isn’t a one-time thing.”
The implication was, if Trump lost, Trump’s focus on working Americans would go on. All the while, the Trump campaign was expressing optimism. I ran into Jason Miller, the communications director, the night before the election and the morning voting began. He said Trump strategists felt very good not just about Florida but about North Carolina and Ohio and Michigan and Pennsylvania and other Rust Belt states. –Star Beacon
Mission Impossible: Trump wasn’t supposed to win and Hillary Clinton wasn’t supposed to lose. All the big money and influence was in Hillary Clinton’s favor. This was the most dramatic and profound presidential election in U.S. history. Why? If Wall Street heavy hitters and big banks endorse someone like Hillary Clinton, if Hollywood celebrities endorsed her, if you’re Clinton and former and acting U.S. presidents are you, if 51 national securities advisers tell you Trump is bad news, if every poll in America tells you Trump is losing to Clinton, if prominent Republicans from their own political party cross party lines and publicly announce they are going to vote for the Democrat nominee , if feminist supporters are galvanized against you and are voting for Clinton – if a tape surfaces just 2 weeks before the election incriminating you in some sexist, misogynist controversy, you’re not supposed to win a presidential election. You’re not supposed to be even close to winning. Yet Trump pulled off the upset win of the century. Donald J. Trump’s presidential election win may just go down as the most stunning political upset in history.