Why is it so hard for Democrats to hold the White House when they don't run an incumbent?
Haven't since 1856 (yeah, I know, I know...Gore won the popular vote...that's why I said it was hard, not impossible).
It's a quirk of history arising from the post-Civil War Republican strength and FDR running 4 times.It also seems to be that Democrats have a knock-down, drag-out fight for the presidential nomination when they don't have a sitting president in the running (1860, 1896, 1920, 1952, 1968), thus weakening them for the general. Republicans...not so much.
Roosevelt's win was narrower in '44 than '40...I think a nonincumbent Dem would've probably won in '40 due to the improving economy (after the '37 recession) and because Democrats were the nation's majority party, but '44's unpredictable. It's difficult to imagine FDR not running (much easier to imagine him not running in '40).