Just a quick start for a mini-TL here. It's a little rough around the edges, as I basically just rolled with this idea the second the light bulb went off. I'll expand on this idea if it goes over well.
A Rainbow Fades
aaaaaJesse Jackson was barely able to win the Democratic Nomination in 1988 after the poor performance of Massachusetts Governor Michael Dukakis, mainly due to the surprisingly successful campaign of Delaware Senator Joe Biden. His nomination came as a shock to many and nearly every worry in the book was brought to the forefront. Many worried that America wouldn't be ready to elect a black man as president. Others were simply worried about his experience (the lack thereof) and his extremely liberal platform (which could easily be considered farther left of even Walter Mondale).
aaaaaThese worries were shared by higher ups in the party as well. Many of the possible running mates Jackson had attempted to court had outright refused, convinced that their careers would be over if they tied themselves to the ticket. Jackson tried to find a running mate who could best relieve fears over his inexperience, while possibly adding ideological balance to the ticket. His choices were slowly whittled down until these first two considerations were almost completely thrown out. Most of the possible choices who hadn't refused simply weren't to Jackson's liking. Eventually he resorted to choosing someone he had previously dismissed, Pat Schroeder of Colorado. Jackson disliked the idea of choosing Schroeder, mainly because he thought that the public would see it as a political stunt and a reminder of the Mondale campaign. But, at this point he had soured on the idea of a ticket balancer. She was ideologically similar to him and inexperienced, but he was actually favorable towards the idea of her as his Vice President. So for the second time in a row, the Democratic ticket nominated a female running mate.
aaaaaInstantly the media began to attack the new ticket from all sides. The right attacked the ticket for its inexperience and radical platform. The Democratic ticket attempted to spin the right's criticisms as racist attacks, but the point of Jackson's race seemed to be brought up more by the left and the American people largely rejected this spin, seeing little substance to it. Jackson performed poorly in the debates, failing to explain several of his positions and refusing to compromise on others. Criticisms of Jackson's nuclear plan were made a major part of the Republican campaign (much to the surprise of Jackson), which managed to fairly easily paint Jackson as a "peacenik", with "no regard for American safety". The Republicans also made a point of Jackson's "Hymietown" comment from the '84 campaign, using it to such a degree that it turned much of Jackson's civil rights focused base against him. By the end of the campaign it had become clear that America had rejected Jackson's platform and Jackson himself wasn't ready for this campaign. Some polls showed Jackson winning as low as two states (a defeat as terrible as Mondale four years earlier), while others showed him winning a few more but not enough to nab more than 50 electoral votes. The Democratic ticket would lose, it was just a matter of by how much it would lose.
aaaaaIt was easily the worst defeat the Democratic party had ever seen, as well as being the worst defeat for any major party nominee in history. Bush had won every single state, only losing D.C. Bush's monumental success translated in a small degree down ticket as well, establishing substantial Republican majorities in both the House and Senate. Jackson's career was over, and the Democratic Party had suffered a defeat it might not recover from. It was a dark day for the American left.
EDIT: Removed ironic Dianne Feinstein