I think Montreal would be better.. especially at D.
Even an all-timer like Tretiak is < Roy so Montreal is just plain stronger on the back end.
At forward Montreal is better and deeper everywhere except LW.. even then Montreal's LW is strong..
Having a much longer history certainly works in Montreal's ...
Set a time period from the mid 60s onward? They do get a whole country to choose from ... but it's still fun. Mtl loses Rocket, Harvey, Plante, Moore, Boom Boom , maybe Henri doesnt make the team anymore, Beliveau is older, Morenz, Lalonde, Malone, Joliat...takes the era arguments out of the equation to a large extent. then the argument is Mtl gets more modern players and maybe "better."
Moving them around for chemistry... Beliveau is obviously still 1A and the captain as he was 34 in 1965 but also won the Conn Smythe and won another 5 Cups from 65 onward.
Went with a checking line, but that could be a huge mistake the way these teams would play. I think Bowman would go checking line, but with that defense and goaltending maybe not, or maybe he doubles down on d. Leclair was still developing as a Hab. Gainey was a monster against the Soviets, so building around him makes sense.
Shutt - Lemaire - Lafleur
F. Mahovlich - Beliveau (C) - Cournoyer
Gainey (A) - Carbonneau - Muller
Pacioretty - Turgeon - Naslund/Damphousse
Robinson - Savard (A)
Lapointe - Subban
Laperriere - Chelios
JC Tremblay
Roy/Price
Dryden
Also 10 of these guys were/are captain(s).