This is a multi-billion dollar business so Gary does what is required of him. I don't see what the big deal is, it's a cold, greedy world out there in case someone hasn't noticed and the NHL as a business is no different.
In terms of rule changes I think he and the NHL have done a good job. A weaker man in charge during the last few years and we'd have women's rules right now.
If someone insists on booing the man, doing so at the draft is ok by me but doing so when the Cup is being presented is seriously lame.