Off the top of my head you would have to consider several of the Yankees dynasty teams (at least four dynasties), Canadians (same number as Yankees), 1960s Celtics, 1970-80s Steelers, 1990s Bulls.......but the one I put ahead of them all was the 1980's Edmonton Oilers, who won five cups, and if they weren't a small city team in Canada and were able to keep Gretzky, Messier and Kurri together among other great players on that dynasty, they probably would have won 8-10 Stanley Cups.
The 1983-84 Oilers team average 5.5 goals a game, the following year their top line had two 70 goal scorers (Gretzky 73, Kurri 71), 1985-86 they didn't win the cup thanks to Steve Smith's own goal in Game 7, but that team boasted three players with 130+ points and 50 goals scored. After winning two more cups the Great One was traded to the Kings at the age of 28 and Coffey traded to the Pens (25 years old) in 1988, which didn't stop the Oilers from winning their 5th cup in 1989 led by Messier.
At their height they won 4 cups in 5 seasons and 5 in 7, but if they were in a major market like Chicago, New York or even Montreal, like I said I don't see why it wouldn't have been more.
The 1983-84 Oilers team average 5.5 goals a game, the following year their top line had two 70 goal scorers (Gretzky 73, Kurri 71), 1985-86 they didn't win the cup thanks to Steve Smith's own goal in Game 7, but that team boasted three players with 130+ points and 50 goals scored. After winning two more cups the Great One was traded to the Kings at the age of 28 and Coffey traded to the Pens (25 years old) in 1988, which didn't stop the Oilers from winning their 5th cup in 1989 led by Messier.
At their height they won 4 cups in 5 seasons and 5 in 7, but if they were in a major market like Chicago, New York or even Montreal, like I said I don't see why it wouldn't have been more.