The whole "Bring Roy 'Cuz he's a winner" is more than just a bit ridiculous. The reason why he's considered a winner isn't because of his exec career (One Mem Cup and, I think, Zero President Cup is rather weak when you have more ressources at your disposal than everyone else), but because of his extremely successful playing career.
His extremely successful playing career, and, thus, the "Winner" tag, came about because he was a generationnal goaltender. Arguably the greatest of all time. This is why he won. Make him an average NHL netminder, and Roy doesn't win any Cup here, and probably doesn't get traded to a powerhouse who only lacked a netminder, on his way to two OTHER Cups and another Smythe.
But... What the hell does being a generationnal netminder with an uncanny ability to perform in the clutch has anything to do with managing a hockey team? And, frankly, I'd rather have him as a head coach than as a GM.
We should leave Romanticism firmly in the 19th Century.