Shisou:

Do I win?

Nope. The two remaining masks went with Jack's last human body into the Void when you kill him the first time. Therefore, they wouldn't be floating around Albion for the Hero of Bowerstone's descendants to find. I give you credit, though. It was certainly one of the better, "Let's bring Jack back" ideas I've heard. I particularly liked the bit about the Hero of Oakvale being slowly corrupted by prolonged exposure to the mask. Only other problem I see here is that this corruption would have affected the Hero of Bowerstone somehow, would it not?

Ultimately, I agree that if LH decides to bring Jack back, they can change "history" however they see fit to make it happen. This is more an exercise in personal entertainment.

squidproquo:

You are a murdering machine, sir.