About the only way Bradley could have won would have been for there to be a major backlash against Clinton within the Democrats, and then for Bush to make some major blunder in the campaign. Bradley would have done worse than Gore did in the general if nothing else had changed, and he didn't really have any chance of winning the nomination with Clinton being so popular.
One of the few things bradley was good at was "attack debating". When he debated people of an opposing party, he was vicious and pretty good. If you thought Gore man handled the 2000 debates, you would have been tickled pink by Bradley.
Unfortunatly, Bradley didn't even try to attack Gore in the primaries. He tried to get people to vote for him rather than against Gore. Democrats just don't think that way. Almost all of them vote against something/someone rather than for something/someone.