Bettman's resume' is checkered with notable failures.
With Friday's announcement that the NHL's Winter Classic has been canceled, the current lockout has claimed its most significant casualty thus far. Gary Bettman's already got the lost season of 2004-05 and the "No Goal" controversy on his record. So does this cancellation represent one of his worst moments as NHL Commissioner?
One thing is for sure. There's plenty to choose from.
Whether it's Bettman's failed expansion agenda or the lack of the NHL's presence on ESPN, hockey fans can point to numerous negative transgressions during his tenure. Compiling a list of those is much easier than coming up with the positives he's brought to the league since 1993.
Ahead, we're going to examine the four worst moments in Bettman's 19 years as Commissioner in the wake of losing the NHL's signature event.
Last year's Winter Classic was held at Citizens Bank Park in Philadelphia.
Since its inception in 2008, the Winter Classic has become a national showcase for the NHL. It brings hockey from the back burner of the American sports world to the forefront.
College football used to own New Year's Day, but since the inception of the BCS, fewer premiere bowl games have been played on January 1.
That's allowed the NHL to steal the spotlight with their annual outdoor game.
This season's version was set to feature a Canadian team for the first time in the event's history. The Detroit Red Wings were scheduled to host the Toronto Maple Leafs in an Original Six matchup at Michigan Stadium in Ann Arbor.
It surely would have drawn an NHL-record crowd, somewhere in the neighborhood of 100,000 people. The amount of money and exposure the league loses from its cancellation is immense and can't be over-stated.
Bettman bears this responsibility more than anyone.
If he hadn't helped to prepare such an insulting offer for a new CBA over the summer, a deal might already be done. Instead, it left the two sides miles apart and created a sense of animosity between both parties.
Little did Bettman and Donald Fehr know that after appearing in front of Congress together, they'd become adversaries four years later.
The fact that this is the third work stoppage under Bettman's leadership should say it all.
The NHL is still the only professional sports league to cancel an entire season. The effects of that decision are still being felt, and we'll touch on that in a little more detail shortly.
Obviously, since the axe came down on the Winter Classic as a result of the ongoing lockout, we're ranking one higher than the other. And although the September 15 announcement wasn't unexpected, that doesn't change the poor reflection it had on the Commissioner.
Like it or not, he has become the face of all that's wrong with the NHL's current situation. Greed, power, arrogance and egotism are just a few of the words his image evokes from hockey lovers.
Because he's been down this road before, fans are less tolerant than ever of his robotic demeanor.
His canned statements about the "good of the league" and its "financial stability" are falling on deaf ears. Especially when the NHL and its owners plead poverty despite coming off another season of record-setting revenue.
Bettman can never escape awarding the Stanley Cup for a goal that shouldn't have counted.
With the hope of the current lockout coming to an end still prevalent, we're ranking the "No Goal" debacle from the 1999 Stanley Cup Finals higher.
This was another first in pro sports on Bettman's watch. Never before and not since has a league's championship been decided on such a blatant violation of the rules.
At the time, Rule 78-B stated:
Unless the puck is in the goal crease area, a player of the attacking side may not enter nor stand in the goal crease. If a player has entered the crease prior to the puck and subsequently the puck should enter the net while such conditions prevail, the apparent goal shall not be allowed.
It was a source of controversy that entire season, as more than 100 goals were disallowed because of it.
But when it mattered most, the league inexplicably ignored it. The NHL tried referencing some ridiculous loophole as to why Hull was legally in the crease.
Yet, years later even Bettman himself all but admitted the goal was tainted. The fact the league changed the rule shortly after the Finals was an embarrassment to the Commissioner and hockey itself.
Bettman announcing in February 2005 that there would be no hockey that season.
Unless the current lockout wipes out another full season, the worst moment of Gary Bettman's career as NHL Commissioner so far came with the cancellation of the 2004-05 season.
The damage that did to the league's standing in the sports hierarchy (especially in the Unites States) was devastating.
For years afterward, the NHL toiled on obscure cable channels like Outdoor Life Network and Versus. The '04-'05 lockout resulted in ESPN turning their back on hockey. Bettman has done nothing since to rectify that.
Sure, the new TV deal with NBC and the NBC Sports Network is lucrative. However, it still keeps the majority of televised regular season games on a channel that most consumers don't get.
More than anything, it took the game out of the minds of the common sports fan for 18 months. Not until the popularity of the Winter Classic did the league regain any kind of presence with what you'd call casual hockey fans.
Mr. Bettman has made a lot of mistakes in his almost two decades running the NHL. Only time will tell if the worst one becomes him repeating history.