Stan Bowman - Chicago. He repeatedly has to trade players who out value their usefulness to his team. Saad is a great player, but they couldn't afford the cap hit and there are plenty of examples. He trades a player like that for picks/prospects to re-stock on low cost effective players, took a big risk in giving Toews/Kane massive contracts that haven't backfired yet. (10.5mil caphit)
He pays the price to keep those he needs, sends packing the guys he doesn't in order to recycle them into cheaper more cost-effective players. Went on a limb and go Panarin, got plenty of players who weren't as effective on other teams as they are on his. Knew which players to keep around even if it seemed risky and which to move which also seemed risky.
Eventually, his risk vs reward might dwindle, but by the time it does his team already has 3 cups, 2 of which he was the GM for. The guy takes big risks IMO, but he has such a good success rate that it makes it seem farm less risky in retrospect.
Like I said, he'll overpay to keep the guys he knows he needs, and trade away players he doesn't without batting an eyelash, and he'll do it when their value is at a perfect time to do so.
HM: Dean Lombardi, and subsequently he has 2 cups to his credit too.
Rutherford didn't take too many risks since the trades he did were shrewd and IMO pretty lopsided. Anyone could've told you they were wins when they happened, but I admit some were more obvious wins than others.
