I actually think Gerry has a good chance, although I'd probably still go with Jiro. I feel like Jiro not being the better technician may really spook him for a little bit, when he finds out his normal opening up tricks don't work. It'd be a great fight at a high-level. Despite being able to write a book on the techniques in this muthafucker, I honestly think it'd come down to Jiro not being as patient. He'd out-work Gerry IMO. I love the image of these two trading in the pocket, though. Both men throwing beautifully structured shots and not having to fight ugly due to it being a rare case of a southpaw-on-southpaw closed stance.
I'm thinking Watanabe, competitive but clear. I favor his technically brilliant offense over Penalosa's terrific defense.