President David Boren

David Boren is an interesting guy. A Conservative/Centrist Democrat from Oklahoma who Barry Goldwater praised as somebody who ought to be president, Obama had on his national security team, Perot wanted him as a running mate in 1996 and Bloomberg contemplated as somebody who'd be a good running mate in 2008.

How could Boren become President?

I think the easiest way is for him to be picked as somebody's Vice President. Clinton considered making him defense Secretary in 1994 and Gore in 2000 wanted somebody tough on defense as his running mate, so perhaps Gore-Boren could work?

Alternatively Boren might work as Obama's running mate (he served on his intelligence advisory board in the first term).
 
Making him Vice President works, like you said, but aside from that he'd probably have had a decent opportunity in 1992, particularly if you manage to get Clinton out of the race.
 
I think Boren was too conservative even to get the Democratic vice-presidential nomination. (Yes, there was Bentsen, but Oklahoma wasn't Texas in terms of electoral power, and was even less likely to vote for a Democratic presidential nominee--unlike Texas, it didn't even go for Carter in 1976.)
 
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