1988: Jackson and Dukakis, Unlikely Democratic Rivals

In 1988, Rev. Jesse Jackson and Massachusetts Gov. Michael Dukakis formed a political odd couple in the Democratic primaries, with Jackson's bold liberal campaign pushing a populist Rainbow Coalition agenda while Dukakis positioned as the pragmatic frontrunner. Jackson stunned the establishment by winning key states like Michigan, briefly leading in delegates and forcing Dukakis to scramble, but Dukakis clinched the nomination after Wisconsin and went on to lose big to George H.W. Bush.