Measuring success can be different things to different people, and the answer will vary depending on people's expectations.
I think Bettman has succeeded in keeping a league going that at times has had no business continuing. While fans rue the days the lockout started, without the second lockout, there may be a LOT less than 30 teams in the NHL. With the way costs were moving for a small subset of teams (Montreal, Toronto, Boston, Philadelphia, Rangers, Detroit, Anaheim, Los Angeles, and Dallas) it was only a short amount of time before they rendered the rest of the league uncompetitive. The salary cap (for better or worse), changed that. As has been stated...he has increased revenues from $700MM in 1992 to $2.8B this season, player salaries have increased from $344,000 (93-94) to $2.2MM, attendance was at an all-time high, the TV ratings were at an all-time high from a regular season perspective. All are higher than the pre-lockout year of 2003-04 (no other sport in North America can claim that). So, in a financial sense, he has succeeded.
He has not succeeded in warming the fans to him. I'm an open-minded person, I've been watching hockey since the early 70s, been a hockey historian/writer since the mid 80s, and have done a statistical analysis on a lot of what is out there.....and the game is not the same as it was 20 years ago...........or 30 years ago....and so on. I'm not so sure that it's Bettman's fault as he does have 30 bosses, but the shootout - arguably the worst thing to happen to the NHL in my opinion, happened under his watch
Bettman's successes
- keeping a 30 team league together
- getting increased television ratings
- increasing league-wide revenues 4 fold
- increasing player salaries 6 fold AND keeping them in line with the cap
- increased parity - in a 21 team league - the last week of the season rarely had any effect on who was in and who was out...but in the last 8 seasons at least one playoff spot has been determined on the last weekend of the season
- continued increased attendance (the NHL has had one negative increase since 1967)
- Olympic participation (prior to NHLers being allowed to compete, professional players from other European leagues participated)
Bettman's failures
- the shootout (I know he doesn't have a vote - but he does have the power to say...'It's a bad idea guys')
- two lockouts (I know these were mandated, and I know neither side should be expected to give in to the other, and I even developed an interest in poker - but I missed my hockey!)
- relationship with the fans - for whatever reason, he has yet to develop one.
- relationship with the players - prior to this weekend, Bettman had never attended an NHLPA meeting despite promoting a 'continuing dialogue' with the players
Clarence Campbell had a far worse relationship with the players than Bettman could ever imagine, and Ziegler had none, but the lingering animosity is not good.
Has my appreciation of the game been enhanced? Hard to say. I love hockey, I study it, etc....so I can roll with the rule changes as much as anybody (aside from the shootout). There has been a lot of great hockey under Bettman's watch. What does ruin it for me is his smugness, his lack of a relationship with the fans, and the lingering perceived toll that the lockouts have had (in reality, hockey is more popular than ever when you look at the NHL's numbers and climbing enrollment in minor and senior hockey in both Canada and the US) on the ignorant people who feel that they have nothing better to do than bash a sport that they have not taken the time to obtain the facts. I will always watch hockey, and I'm pretty sure I will always enjoy it (until the Western conference brings in the 'designated cherry picker' for overtime). But I doubt any one individual can do anything to enhance, or detract from my pleasure of watching an NHL game.
So, while Bettman has done a lot of things for the league financially that have made it 'more successful', none of it has added, or detracted the pleasure I get watching an NHL game.