Business Democrats and their triangulating was one thing, but an outright conservative Democrat would be a bridge too far for much of the base. Although Cheney would lack Bush's beer-track Southern folksiness, it's not like he'd be up against a very Southern ticket (Gore still would have developed a reputation as a creature of D.C. rather than Tennessee, it was just the way he carried himself), nor did he have his spooky reputation yet- he would probably even be able to position himself as the sane one in the room versus McCain and then Lieberman. Consider, for example, his April 15, 1994 interview with C-SPAN, where he voiced opposition to invading Iraq. More people stay at home or vote Nader here. It would be a very Nixonian kind of election, where an uncharismatic but clever Republican goes up against Democrats in disarray and knows how to take advantage of it. Florida might actually be the closest state still, not that it would matter.
Vice President Joe Lieberman (D-CT) / Senator Al Gore (D-TN)
Fmr. Secretary of Defense Dick Cheney (R-WY) / Governor George Bush (R-TX) ✓