Cherry is a tool, if he were the commissioner he would be too busy going out of his way to make himself look like a hard (bleep) to worry about the league, although he never would have let Canadian franchises like Hartford and Quebec escape to the US.
I agree that the big problem with Bettman is his focus on the wrong issues. He is always trying to reintroduce rampant scoring but to me that over-inflates stats, and, to me at least, is boring. It's just teams trading goals back and forth rather than really competing. Boards of current and former goaltenders along with league reps. consistently decide against major changes but every season he's back with his ideas about increasing net size and decreasing equipment size. The only merit to his argument is that in the new-age, butterfly dominated world of goaltending equipment should be updated to meet the style, and even that is a weak argument IMO.
He ignores the fact that hockey could be a staple sport in the U.S. but isn't. Georges Laraque put it best when he asked why teams would open overseas to try and generate interest in the NHL when it can't even generate interest at home. Instead of trying to build up interest overseas he should be worried about the primary market.
He doesn't go with tried and true marketing techniques: in the NBA, great players are always compared to MJ by the league, and it works. Only the media outlets do that here, and comparing the new greats to the old would stop the massive loss of fans of the old NHL.
The fact that the later rounds of the playoffs appear only on VS. drives me insane. Very few people get Versus, and the ones that do don't know it exists. Showing the weekend games on NBC is a step in the right direction but the fact that the network does things like cutaway from a Cup Finals game that's in overtime is also ludicrous.
I could continue my rant but the bottom line is the guy has ideas that are too big and too far into the future for where the league actually is right now.