One of the biggest issues to me is that he isn't a hockey guy. You have a guy who has no history in the sport. Gary Bettman didn't watch Hockey Night In Canada growing up, heck, he probably was getting his lunch money stolen from the American kids that may have been paying attention to Peter Puck. I can say one thing, it definitely shows when there is a leader who is not in love with the sport he runs. Hockey doesn't have any sentimentality to him, and come to think of it Goodenow didn't seem to have a love for the game either. That is why neither of them have/had ever done anything that was actually in the best interests of hockey. You don't lock out the best league in the NHL if you love the game, you just don't.
Here is the thing, I have never been part of the NHLPA, but I have been part of a union. In a perfect world everyone gets a voice in a union at their workplace. But it doesn't work that way. Think of even something such as the Teacher's Unions. The union bosses run the show, not all of the opinions of the teachers. Ditto with the players. Unions can and will get corrupt. Yes, you look out for the players/workers you are representing, but you still need for them to have a job. If you run the business they are working into the ground or help contribute to it shutting down you aren't helping them.
I get it, you are from Edmonton I assume? However, Quebec and Winnipeg left on his watch.