Jeb was always thought to be the conservative wing of the Bush family, and by far the best political talent of the bunch. He would probably have been president instead of George had he won his first gubernatorial race. He lost narrowly, due in large part to a last minute robo-call campaign alleging that, as Governor of Florida, he would abolish Social Security and Medicare.
Jeb definitely comes off as more “with it” than George Jr. does in interviews, but he doesn’t lose the blue collar appeal. Honestly haven’t looked into his politics or positions much but I think he’s electable despite any Bush baggage. George Jr.’s approval’s been on the rise anyway I think, and people probably have an overall positive view of his presidency despite how it ended, especially when comparing to Barack’s. Mitt’s magic trick for the contested convention might be to fall on his sword and offer himself as Jeb’s V.P. Of course the GOP-E would want Jeb/Rubio if it goes totally brokered. Perhaps with a grand bargain among everyone else to give them cabinet positions they could pull it off (Santorum - Health, Newt - Energy, Mitt - Treasury, Paul - Janitor). I’m pretty much ABOBR, so I’d be okay with that.