I think not, although I'm sure he wouldn't have been pro-StoniesEverywhere, either.
That's a good question and not that easy to answer. If you really cared what He thinks then consider that His first miracle was to turn water into wine, not grape juice as Baptists would have you believe. But that doesn't mean weed is ok with Him anymore than "Let him without sin cast the first stone" means that all sin is just fine with Him either.
That's not the question---the question is whether caging adults for using weed is OK with Him. I think that "Render unto Caesar the things that are Caesar's and render unto God the things that are God's" and "Put away your sword" strongly suggest otherwise.