My own speculation leads me to conclude that he's in very good standing with a core group of hardline owners, and always has been. I think this group includes Jacobs, Snider, AEG, formerly Wirtz, Leipold, formerly Hotchkiss and the Oilers previous ownership group. He isn't on good terms with Ilitch or Dolan, for example, and I'd imagine MLSE are at odds on at least one matter (the Nov 2006 letter on territorial rights). Obviously Moyes went his own way, in a big way. What about ASG? All speculation really.
With regard to Calgary and Edmonton, they really were hurting, but it was currency instability coupled to the need to pay out in USD while earning in the CAD.
I also believe Bettman has taken several of his cues from the NBA. I don't view this as an evil thing, just an objective observation that several of the more powerful owners in the NHL also own(ed) NBA teams. What one learns in one league may seem to be applicable in the other-- and to a certain extent this may be true.
Thus they all may be "comfortable" with the approach and with each other.
If you aren't going to have a sports league that has relegation built into it along the lines of European leagues, then how do you breach the gap between massive markets and the 'barely big enough to register', who all have somehow come together as equals in one league?
As you note, revenue sharing is the real answer from the revenue side of things, but it's completely unacceptable from the ROI side of the equation. Each owner owns one team, not shares in the league, and thus each owner has invested vastly differing sums of money (Molson group at $500+ MM vs Vinik in TB at $100 MM + assumption of that year's remaining operational costs).
Cap systems are an evolutionary change to this reality--- increasing competition for players among a group of teams with vast disparities in income. Why not? It's that or a luxury tax or soft caps, etc., but if you're going to stick to the single league of equals model, you have to get creative. The other factor that offered protection to lesser equals was a restraint on free agency and lack of information for players on salaries. That has also changed drastically in the past two or so decades.
In a sense, the cap system with some level of revenue sharing was palatable to both big and small because both benefited from the expected savings the cap would bring. The bigger teams would spend less money overall -- in spite of writing the big transfer checks -- because they'd also spend less on players due to there being a cap. The smaller teams would get help paying for the players. It was supposed to be a win/win.
Where I believe it went off the rails is that the NHL treated the small Canadian markets similarly to the US smaller revenue generators. It was supposed to be a one size fits all solution. I guess no one expected the USD to crash against the CAD. The other factor is that everyone promised 'winning' so the teams most in need of a boost (the small revenue teams) were usually the worst in on ice performance as well. Maybe the 'Any Given Sunday' promise was the wrong to make?
Today we're at a point where the Canadian teams have driven a good chunk of the cap growth, while any US growth only feeds the fire, so-to-speak. Did anyone really expect the ceiling to be at $64 MM within five years of the lockout? Had the growth come from the weakest teams [who ostensibly were going to benefit from parity], it might have worked out. Only problem is that you weren't going to have the big boys sitting on the sidelines so the others could catch up--- at their expense.
It really may be that the real problem is simply structural. Should Sheboygan be competing head on with Manhattan? Europeans approach it differently. Why have US leagues chosen this direction?
(I think the answer is the TV network expectations, but that assumes those guys actually know what they're talking about.... I'd say they don't if they just keep showing the same 6 teams over and over. I don't know really, to be honest.)
