Quick team I through together based off a comment from another site.
Not the oldest team possible, but pretty close to it while trying to remain a "good" team.
Could this team, or one similar to it win a Stanley Cup?
Everyone bags on old teams and "last hurrah" teams. I think they are very much capable of winning a cup. Granted this team is star studded.
Watching old teams who are muddy and slow is enjoyable to me. They have to play calculated and intelligent. A team that has overwhelming talent is fun to watch, don't get me wrong. But watching the gamesmanship of a team like this would be something special. Obviously it's a different era than 10 years ago, and a lot would need to go right for a team this old to win 16.
Way before the cap era, the 1967 Leafs had lots of oldies.......Bower and Sawchuk in net, Horton, Stanley, Pronovost, Baun on defence, Armstrong, Kelly, Pulford forwards.