Bill Clinton selects Al Gore 2

  The stars were aligning for Clinton, and this mistake didn't hurt him.  Much more significant than choosing a wooden Washington Insider was the fact that J. Ross Perot hated George H. W. Bush so intensely, that he was motivated to run on the "Independent" ticket, gathering millions of petition signatures, putting him on the ballot in all 50 states.  Coupled with Bush's relative overconfidence, the death of Lee Atwater and the most pom-pom pumping press corps since Kennedy, his 43% was just enough. 

After the election, while the democrat party zealots were arranging the cabinet, good ol' boy Bill asked what was perceived by most as a stupid question.  Gore icily sneered at him, "get with the goddamn program! "  They didn't exactly get off on the right foot.