It’s a fascinating thought experiment: Could Trump have done to the Democrats in 2016 what he did to the Republicans? Why not? There, too, he would have challenged an overconfident, message-challenged establishment candidate (Hillary Clinton instead of Jeb Bush). He would have had an even smaller number of competitors to dispatch. One could easily see him doing as well as or better than Bernie Sanders—surprising Clinton in the Iowa caucuses, winning the New Hampshire primaries, and on and on. More to the point, many of Trump’s views—skepticism on trade, sympathetic to Planned Parenthood, opposition to the Iraq War, a focus on blue-collar workers in Rust Belt America—seemed to gel as well, if not better, with blue-state America than red. Think the Democrats wouldn’t tolerate misogynist rhetoric and boorish behavior from their leaders? Well, then you’ve forgotten about Woodrow Wilson and John F. Kennedy and LBJ and Bill Clinton.
Not sure how I feel about Trump running as a Democrat. While I have deep reservations about the guy being in the White House (regardless of what platform he runs on), I find myself agreeing with many of his positions in this scenario, and believe his charisma could have allowed the Democrats to regain their status as the party of the working-class. It's really a shame he started the stupid "birther" movement and sided with the climate skeptics, I might have otherwise supported him last year.