IOTL, New Jersey Senator and former New York Knicks star Bill Bradley was the lone challenger to then-incumbent VP Al Gore in the 2000 Democratic Primary. Running to the left of Gore, he didn't win a single primary, and took only 21% of the vote.

Your challenge, as the tin suggests, is to both change the outcome of the primary that year and then have Bradley go on to win the Presidential election. A longshot, I know, but i'm curious to see if anyone can think of a way to achieve it.
 
In late 1999/early 2000, After years distancing himself from Bill Clinton's indiscretions, an employee at a massage parlor appears on FOX News and tells the world that Al Gore had had his won "indiscretion" with her. Gore's numbers tank, and Bill Bradley presents himself as an alternative, unscathed by the seedy personal lives of the Clinton administration. Voters see him as a breath of fresh air, far from the trashiness of the Clinton admin. and the monarchist undercurrents of Bush's rise. Bradley ekes out a narrow primary win against Gore, with much of the Democrats of the Midwest breaking for his old-fashioned liberalism (no doubt helped by the endorsements of Tom Harkin and Richard Gephardt). Bradley selects Bob Graham as his running mate to shore up support amongst moderates.

With Gore out, the Republicans are now positive that they'll win the general election, and as such, they no longer have to play nice with Pres. Clinton. Afraid of being reduced to a lame duck, Clinton backs away from interest rate increases that, in OTL, softened the blow of the dotcom bubble. Despite this being done as a goodwill gesture to the GOP, the Democrats are successfully able to portray the burgeoning recession as the result of conservative fiscal policy (Bradley being the new standard-bearer instead of Gore helps this along).

On Election Night, Bradley narrowly beats Bush with a margin of 273 to 265, having barely won New Hampshire and Florida.
 
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