I've of course noted that the Democrats are really bad at picking their own candidates based on "electability" (Howard Dean Would Have Won), but it's also become clear that the leadership is really bad at picking their opponents. We already knew that the Clinton campaign elevated Donald Trump as part of a pied piper strategy, but now thanks to Brian Abrams's Oral History of the Obama administration, we know that the Obama administration was elevating Trump too (thanks to Corey Robin for reading and publishing excerpts from the book):

David Plouffe, Obama campaign manager: "There was strategy. Lifting up Trump as the identity of the Republican Party was super helpful to us. The president went out in the briefing room to present his long-form birth certificate, but really to continue the dance with Trump. Our view was lifting Trump up at the White House Correspondents' Dinner, you know, as kind of the example of the Obama opposition. There was a strategy behind the material and the amount of time we spent on Trump. Let's really lean into Trump here. That'll be good for us."