Crosby has won three cups, not two.
Anyway, even with the percentage argument, it is still a difference of over $4 million/season in cap space. I think Chia made a mistake signing Russell to a 4x4 instead of locking up Draisaitl and McDavid first. Now with McDavid's deal seemingly set, not only is Chia now having to worry about signing Draisaitl with less than $10 million in cap space (iirc), he has to worry about teams offer sheeting Leon for over an $8 million cap hit. I think Edmonton would be lucky if Draisaitl gets under $8 million, but that team is going to be handcuffed when it has over $20 million locked up in two players, and around another $10 million for non-core pieces like Lucic and Russell.