Al Gore's big mistake was picking Lieberman as his running mate.
From Easter Lemming Liberal News
He thought it would bring moralists who disliked Clinton to the party and carry Florida's Jewish vote. In reality, only a minuscule percentage of voters pay attention to Senators or politicians outside of their home state. While it may have helped marginally in Florida it reinforced an image of the Democratic Party as a collection of liberal special interests.
Instead of an East Coast wealthy Jewish Senator who is liberal on domestic policy but conservative on moral and foreign issues a Gore pick of moderate conservative Senator Graham of Florida would have helped in Florida, the entire South, and the overall vote.
Why? Sen. Graham is from Florida, he is from the South, and his pick nudges the party more toward the perceptual right/left center sweet spot. All of these are factors in the presidential election electoral college game.