In the 2000 election, Donald Trump briefly ran for the reform party nomination against Pat Buchanan but eventually dropped out. What if Trump had instead sought the democratic nomination and gotten it? Would he have a chance against Bush?
I have a very hard time seeing Trump getting the Dem nomination in 2000. Gore had the party machinery locked up. If there was an opening for this, it was 2004 with DT running on an antiwar platform.