My guesses:
2017-2021: Last breath of a dying tradition, but one that's more outsidery and has a vague moderate reformist view (dunno here, I suppose Sandoval could work?)
2021-2029: Liz Warren (diehard liberal, defies tradition of being too extremist due to her charisma and the failures of a previous president, etc.
2029-2033: Someone more moderate but still on your side and has a lot of good Washington experience (someone said Bennet, this works IMO)
After that it gets trickier due to a lack of candidates by this stage. Does the 2040-2048 president become Chelsea Clinton?
