In an alternate universe where he never had his scandal, I think he could have had the biggest landslide of the 2008 candidates. Definitely the odd man out of his time. Populism was as dead in the immediate aftermath of 9/11 as neoconservatism is today.
But in 2020? Sure, Democrats are trying really hard to seem folksy now, but it's paired with the Kerry kind of smug cosmopolitanism that ultimately takes precedence. I just don't see him fitting in with the modern party.
That's what's interesting about Warren -- she is like the personification of that weird mix of "folksiness" and "cosmopolitanism" that defines the Democratic Party today. How could you do that better than being born and raised in Oklahoma yet representing Massachusetts, being a populist on the one hand and someone palatable to party elites on the other? I don't think you could create an individual who better epitomizes the word "Democrat" today in a lab if you tried. Which is part of why I suspect she'll ultimately get the nomination. She's just closer to where the party is at right now than anyone else.