gambling back-to-back with JTs against same foe

[AragornX151]

Hand 1 won't work unless the opponent fits an incredibly thin stereotype of live players (which some do, so if this guy does, fine). This is awful in a vacuum, but I've played against plenty of fools live that I'd try it against, because they're convinced any river c/r is the nuts and they'll be damned if they fall for it. So maybe it's OK if this opponent fits the description.

I would fold hand 2. I don't see what you could be ahead of (despite results) unless your opponent is a maniac.