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I had Jay Harrison on my list, but figured because he's had a somewhat decent career he didn't count. But "guys that turned out OK but were discarded by the Leafs" could be another list.
Lonny Bohonos
Carter Ashton. Thought he'd be able to become a full-time NHLer somewhere. Still don't think Carlyle used him properly, and that messed him up.Also really thought Matt Finn would have cracked an NHL lineup by now.