
My pick would be the politicians of Virginia’s reconstruction-era Readjuster Party, because it’s so unexpected. It was founded by this dude, William Mahone. He was a confederate general and railroad tycoon. So that comes with some expectations as to his policies. But astonishingly, his party was a populist coalition of poor black and white voters, and it created the first state-funded black university in the whole country.
It’s just so unexpected that a bunch of wealthy ex-confederates ended up leading the party who would significantly progress black rights, create public education in the state, and seek to dismantle the power of the planter elite. Formerly enslaved people were elected by this party alongside confederate generals.