George H. Bush in '88: Your successor will be the fat lecherous hillbilly from Arkansas who bored everyone to death introducing Dukasis at this year's poorly received Democratic National Convention! And the enviro looney from Tennessee who got killed in this year's Democrat primary will be his running mate!
Clinton in '92: Your successor will the son with the same name of the 1-term geek you just defeated! He's 46 years old, has never been elected to anything, recently gave up heavy drinking, and owns a baseball team in Texas now. Watch out for this guy!
George W. Bush in 2000: Your successor will be an obscure backbencher Illinois State Senator who just ran a failed campaign to oust a unpopular black panther Congressman! Oh yeah, he also has a history of using drugs, attending a church that claims Reagan invented AIDS, and a weird African name that nobody can pronounce, but reminds people of Arab terrorists.
So a guy becoming President when his most recent office ended in him being slaughtered for re-election by an empty suit politician's kid? Well, stranger things HAVE happened...