Larry (one punch) Robinson has to be one of the toughest of all time. Didn't fight much but it was usually over with one punch. (He KO'd Shultz in the Forum). And believe it or not Jim McKenny of the Leafs was a tough dude (altho not a heavyweight). Derek Sanderson and McKenny has major brawls in Junior and Sanderson always said McKenny was the toughest he had ever tangled with. I did see McKenny tangle with Moose Dupont once and Mckenny won. But without a doubt Larry Robinson was the King !!!
Stan Jonathan took out Pierre Bouchard who towered over him back in I think it was '77 or '78. Jonathan fought all the time and never lost it seemed. He killed Lorimer back in '80 during their playoff series.
Jonathan was another great fighter, especially for his size.
Of all the players I can think of one guy that never ever seemd to lose a fight was Wayne Cashman. I dont know why. I mean not that Cash wasnt tough, he certainly was, but he didnt rack up the penalty minutes that others did. I can think of a brawl back in 1980 where gary Howatt of the Isles gave Cash a sucker punch and got a good head start on him, after about 20 seconds Cashman was beating him and I'm sure Howatt was regretting it. But I've seen other brawls he's been in and fights and he never seems to lose.
when I read the title of this thread that was the fight that immediately came to mind. Howatt absolutely Pearl Harbored Cash but didn't have the upper hand for very long.
That series was filled with some great matchups... Cashman-Howatt, Milbury-Sutter, O'Reilly-Gillies, even Ray Bourque threw a couple of punches in that one.