Are you sure that you're not conflating debate skill with being correct? Also, I may be mistaken, but I have always considered Jimmy's position to be that while Trump would be worse than Hillary while in office, the long-term consequences of having Hillary would be worse for progressives since electing her would "prove" to the establishment that Neoliberal policies and candidates are the way to go. As it stands, I don't see how either Jimmy or Sam was meaningfully wrong on this issue. I ended up voting for Hillary because I live in Ohio, but I did not enjoy the experience and I am very much on the fence about whether or not I made the right decision.