Everyone ranks players differently. It is the same in soccer - who is the best of all time? Pele? Maradona? Eusebio? Garrincha? CR7? Messi? Di Stefano? I think it is a bit more nuanced in football because of how many different leagues there were in addition to eras.
For me, it all comes down to how good were you against your peers during your career? Orr is amazing and weirdly still underappreciated by many, but he was head and shoulders above his peers. Iginla basically had 25% more goals in 2001 than anyone else in 2001. If you watched him play, he was probably the most complete and 'perfect' player in the game (somewhat like Ronaldo from Brazil was in a way). Iginla scored goals, he was underrated as a playmaker, he would fight, he would play physical, he was great defensively, he was amazing along the boards or in the middle of the ice, and he was a true leader out there. He was an incredibly perfect player and was the best player in the world that year (and for a couple of other years I would argue). You won't get that from stats alone of course - you had to watch him, but stats do help in figuring out how a player compared to his peers.
I think Crosby is a generational player, but I roll my eyes when I see people saying: "He would be better than Gretzky if he went to that era". Sure, if he got to bring all the leaps forward in terms of equipment and science (training, nutrition, recover, etc.). There is not telling how far that stuff gets you. I think you always have to rank players in any sport as they were compared to their peers, and then you also have had to really watch them.
Iginla was an amazing player for a many seasons, and if he played in a bigger market, he wouldn't ever be overlooked on anyone's list. Maybe if he had better players to play with, he would have been able to do even more. I will not be convinced that every player who has hit 100 or more points in a season is instantly better than Iginla.
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