2012 and 2016 were the only ones where I was (anywhere near) politically savvy enough to even form a good guess:
2016Hillary Clinton (D-NY): 308Donald Trump (R-NY): 230
While I had come around to thinking Clinton was a particularly flawed candidate, I overestimated the voters' disdain for Trump.
2012Mitt Romney (R-MA): 286Barack Obama (D-IL): 252
I really thought Romney was going to win, and I bought into the idea that the electorate would revert back to 2004 "norms" somewhat. You know, "center right nation" talking points. I thought Romney would do better in New England than he did, I still thought VA was winnable with a good enough candidate for NOVA and I thought Ryan would put us over the top in Wisconsin. What can I say? I liked Romney. We'd all be in a much better place if I were right.