That would have to be Rudy Giuliani. Front-runner to a DISTANT 6th place finish in Iowa, and then another distant 4th finish in a state that he should have had some appeal in, New Hampshire.
He then proceeds to put all his marbles in Florida, home of many transplanted New Yorkers, and loses by 21 pts. I can't remember any other time since 1987 that a SERIOUS Presidential campaign (we're not talking the Kuciniches of the world here) flopped that badly.
As I mentioned elsewhere, Phil Gramm in 1996 might give Rudy a run for his money.
Joe Lieberman in 2004 merits a dishonorable mention.