The Molson family didn't even own the team for 4 of is 9 cups as a GM, the Bronfman family did (who are also incredibly wealthy). And Montreal wasn't the only team with wealthy ownership.
And while there is overlap, there's a difference between how Pollock was a good GM (exploiting the draft and player development) vs. how Selke was a good GM (very intelligent and systematic investment in development teams during the 50s and 60s). And Selke wasn't even a revolutionary, he was Conn Smythe's top lieutenant in Toronto before their relationship broke down.
BTW, the Canadiens were in financial trouble when they hired Selke (and have been a few times under Molson ownership, which is why they've sold the teams at times)
That’s all true — but again, the point remains, Molson money elevated the Habs franchise on a number of levels during the 50s and 60s. Most germane to the subject of their dynasties, it was Molson money that allowed for them to buy a huge chunk of the amateur development system out from under the rest of the league, providing the Habs with a long-term talent stream that other teams could only dream of.
Yes, the Bronfman family owned the team during the late 70s dynasty. But what did they need to do beyond sitting on their hands and reaping the rewards of prior work? The major pieces of the dynasty were already in place, legacies of the Molson era (which is almost synonymous with the pre-draft era and the pre-expansion era).
It’s easier to see the progression of events if you start the story in 1957 when the Molsons bought the franchise. As of that year:
Maple Leafs: 7 Cups
Canadiens: 7 Cups
Red Wings: 7 Cups
Bruins: 3 Cups
Rangers: 3 Cups
Black Hawks: 2 Cups
At that point in time it was basically a 2-tier league which was still being run by the same people and on the same principles as the 1930s NHL. The Habs were owned by the Arena Company and managed by Selke, the Leafs by Conn Smythe, and the Norris family to varying degrees controlled all 4 American franchises, especially the Hawks and Rangers who were little more than support systems to prop up the Red Wings. The Bruins were owned by Walter Brown who was an old-school arena manager and promoter. Selke was probably the smartest of that bunch, but all were rooted firmly in a bygone era.
The Molson family’s purchase of the franchise in ‘57 was superficially another old-school ownership move by a wealthy family, but under the surface it was a shift toward modern ownership — a team financed by a national corporation. In a sense the Habs became a vertically integrated corporation along with Molson, similar to the Flyers with Comcast or the Bruins with Delaware North. That was a game-changer, in terms of producing a cash flow beyond what other teams could compete with. Selke and Pollock were smart enough to know what to do with that financial advantage, investing in long-term organizational development from junior leagues all the way up to management of the parent club.
Compare the above to the Maple Leafs, where Conn Smythe sold the organization to his own son and Harold Ballard, who for decades infamously refused to invest in the organization at all. And even in the present age, with corporate backing and a massive financial advantage, the Leafs have a notorious leadership problem which burns through money and talent in pursuit of profit rather than victory. That’s how you go from tied in the Cup race to down by 10.
And yes, the Habs eventually ended up in financial trouble under Molson. That speaks to how things played out after the Pollock-era excesses of the 1970s — expansion came to a halt, the Habs’ golden era of prospect development flatlined, other organizations were acquired by well-financed modern owners, and one by one they matched and then surpassed the Habs in their capacity to assemble talent. The Canadian economy circa 2000 had declined to the point that American corporate money was required to keep the team stable for a time. And of course the most recent chapter is the cap era, with a robust NHL in a relatively stable Canadian economy where ownership returned to the Molsons in a league where it’s now very difficult to gain any sort of systemic edge through any means at all. Which makes the Habs just another of the 32 organizations, hence the black-and-white difference between the organization’s successes 1957-1979 versus 1980-2025. Those differences certainly don’t come down to pure GM intelligence, they are a direct reflection of the context in which those GMs were operating.