Jim Webb vs. Jeb Bush

[Joe Biden 2020]

So maybe he'd win Oklahoma.

Don't bet on it.  Oklahoma, as a whole, is fond of the Bush family.  We remember HW and W quite fondly, so I think Bushie (not me) would win Oklahoma.  The only knock on Jeb is his support for common core, something the teachers across the state vehemently forced the governor to do away with last summer.  That, and the fact that Jim Webb is as close to a Blue Dog as we've got, might make it closer than past elections, but it wouldn't be enough for Webb to win.

[Joe Biden 2020]

So maybe he'd win Oklahoma.

Don't bet on it.  Oklahoma, as a whole, is fond of the Bush family.  We remember HW and W quite fondly, so I think Bushie (not me) would win Oklahoma.  The only knock on Jeb is his support for common core, something the teachers across the state vehemently forced the governor to do away with last summer.  That, and the fact that Jim Webb is as close to a Blue Dog as we've got, might make it closer than past elections, but it wouldn't be enough for Webb to win.

Could the results in Oklahoma be something like 60-40 or 61-39 in a Bush vs Webb matchup?

Possibly.  I think Webb could keep Bush in the mid to high 50's.