Weren't the Blackhawks used in the early days by the Red Wings to hold players until they needed them? I'm pretty sure they were owned by the same people. I believe Jack Adams traded Ted Lindsay to the Hawks to punish him for trying to form a player's union.
I would think that Montreal clearly is the most storied franchise, but after them it has to be Toronto. When the league was growing, Toronto was the team kids all across Canada grew up with on the radio. I do agree that they have never had that #1 player in the league, but a lot of teams can say the same thing. Until expansion, the best player in the NHL was almost always on Montreal or named Orr.
I'd say, out of the Original Six, Chicago is the weakest. All six teams have a lot to be proud of though, so I think this is a dumb thing to be arguing about.
Best overall Leaf? To me, it will always be Mats Sundin, but that is because I'm biased to the modern era. People forget that the Leafs did have a lot of playoff success under Mats, but they just missed getting to the final level.