If the residents of the District of Columbia had the right to vote since the first presidential election, how would they have voted? Would it have voted Republican in any election?
I think it's likely it'd have voted Republican in 1864. Lincoln blew out McClellan in Maryland and DC was a pretty militarized city in 1864.
1868 and 1872 are possibilities, but I think the Dems would win it both times. 1872 would be more likely than 1868 as a GOP victory.
Given DC did not yet have home rule, it'd be difficult to imagine the degree of intensity Jim Crow voting restrictions in DC would be. Presumably, they'd be present though less stringent than most Southern states. (DC was absolutely a Jim Crow city before the Civil Rights movement, but as far as voting rights are concerned, it'd be more confusing when either/both parties realize they have a vested interest in those three EVs) Post-1872 it's basically impossible to guess given it's unclear what chunk of DC's black voters would be voting.
Either way, lots of blacks or very few voting, I think we could easily guess that DC is 100% safe Democrat from 1932 to when it starts actually voting. (Though Ike would've likely massively overperformed there, I don't think Eisenhower would've won it) It's the period between the 1870s and 1930s that's difficult to imagine.
