Since the league expanded from just 6 teams, which teams have been the most successful?
IMO, the top 10 would be:
1. Montreal Canadiens: 10 cups; 11 finals - 82 total team/individual awards won
Cup winning years (1968, 1969, 1971, 1973, 1976, 1977, 1978, 1979, 1986, 1993)

2. Pittsburgh Penguins: 5 cups; 6 finals - 76 total team/individual awards won
Cup winning years (1991, 1992, 2009, 2016, 2017)

3. Edmonton Oilers: 5 cups; 7 finals - 59 total team/individual awards won
Cup winning years (1984, 1985, 1987, 1988, 1990)

4. Detroit Red Wings: 4 cups; 6 finals - 62 total team/individual awards won
Cup winning years (1997, 1998, 2002, 2008)

5. New York Islanders: 4 cups; 5 finals - 43 total team/individual awards won
Cup winning years (1980, 1981, 1982, 1983)

6. Boston Bruins: 3 cups, 9 finals - 72 total team/individual awards won
Cup winning years (1970, 1972, 2011)
7. Chicago Blackhawks: 3 cups; 6 finals - 47 total team/individual awards won
Cup winning years (2010, 2013, 2015)

8. New Jersey Devils: 3 cups; 5 finals - 33 total team/individual awards won
Cup winning years (1995, 2000, 2003)

9. Philadelphia Flyers: 2 cups; 8 finals - 48 total team/individual awards won
Cup winning years (1974, 1975)

10. Los Angeles Kings: 2 cups; 3 finals - 39 total team/individual awards won
Cup winning years (2012, 2014)