Challenge: Unanimous electoral vote

Reagan came pretty close in 1984.

He could've taken Minnesota, but DC was probably out of reach.

Likewise, Maine and Vermont actually went pretty hard for Landon in 1936 -- Upper New England was the inverse of the Solid South at the time.

I think our best bet is either 1820 (contrary to popular myth, that one elector from New Hampshire didn't vote for Adams because 'only Washington should be honored with a unanimous vote', but because he thought James Monroe was a jerk -- replace him and you're good), or 1864, if Democrats nominate a Copperhead instead of McClellan. (New Jersey and Delaware were close OTL, and supposedly McClellan won Kentucky on soldier votes.)
 
Maybe 1964, if you could get another Dixiecrat to run. That might split up the GOP and Dixiecrat vote and give LBJ all of the votes.
 
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