Since the Conn Smythe Trophy – awarded to the most valuable player in the National Hockey League playoffs – was first handed out in 1965 only six players have won it more than once.

Those six players? Bobby Orr (1970 and 1972), Bernie Parent (1974 and 1975), Wayne Gretzky (1985 and 1988), Mario Lemieux (1991 and 1992), Patrick Roy (1986, 1993, and 2001), and Sidney Crosby (2016 and 2017). Five of the six are in the Hall of Fame, with Crosby surely to be enshrined as well.

Canadiens stars limited for Conn Smythe

That means no members of the Montreal Canadiens other than Roy have won the Conn Smythe Trophy more than once, despite all their Stanley Cup championships in the 1960s and 1970s. Jean Beliveau (1965), Serge Savard (1969), Ken Dryden (1971), Yvon Cournoyer (1973), Guy Lafleur (1977), Larry Robinson (1978), and Bob Gainey (1979) were all recipients of the trophy once.

Not helping the cause of the Canadiens players was the trophy being awarded to someone on the losing side in three of their Stanley Cup victories during that era. In 1966 the Canadiens got past the Detroit Red Wings in the Stanley Cup final, but Red Wings goaltender Roger Crozier was awarded the Conn Smythe Trophy. That scenario played out again in 1968 with St. Louis Blues goaltender Glenn Hall, and then once more in 1976 with Philadelphia Flyers forward Reggie Leach.

Four Islanders players won in four seasons

The New York Islanders won the Stanley Cup four times in four seasons from 1980 and 1983, but four different Islanders players were awarded the Conn Smythe Trophy in that four-season span – forwards Bryan Trottier, Butch Goring, and Mike Bossy, and then goaltender Billy Smith.

As well, the Edmonton Oilers won the Stanley Cup five times from 1984 to 1990, but Gretzky was the only multiple-time Conn Smythe Trophy winner during that stretch. Forward Mark Messier was the Conn Smythe winner during the team’s first Stanley Cup run in 1984, while Flyers goaltender Ron Hextall won for the losing side in 1987. Goaltender Bill Ranford claimed the award in 1990.

Ten active players have Conn Smythe wins

So how many players have a chance to join the multiple-Conn-Smythe club this postseason?

There are 10 active players with a Conn Smythe Trophy on their resume, but three of them missed the playoffs this season – Crosby, teammate Evgeni Malkin (who won the Conn Smythe Trophy in 2009), and Patrick Kane (who won the award in 2013 while still with the Chicago Blackhawks).

That leaves just seven total candidates to pick up a second Conn Smythe Trophy this spring:

Jonathan Quick – Goaltender – New York Rangers

Quick backstopped the Los Angeles Kings to a Stanley Cup championship in 2012 and had a solid year as the backup to Igor Shesterkin for the New York Rangers this past season. However, with Quick unlikely to see the crease during these playoffs unless Shesterkin falters badly (or suffers an injury), he’s a Conn Smythe Trophy longshot.

Alexander Ovechkin – Forward – Washington Capitals

Ovechkin was the Conn Smythe Trophy winner in 2018 when he put up 15 goals and 27 points in 24 games to lead the Washington Capitals to their first-ever Stanley Cup championship. Having led the Capitals in goals again this past season, Ovechkin would be the top Washington candidate to take home the award. The Capitals, however, are the lowest seed in the Eastern Conference side of the bracket.

Ryan O’Reilly – Forward – Nashville Predators

O’Reilly took home the Conn Smythe Trophy in 2019 as a member of the St. Louis Blues, with 23 points in 26 games that postseason. O’Reilly was fourth in scoring on the Predators this past season, and would be behind fellow forward Filip Forsberg, defenseman Roman Josi, and goaltender Juuse Saros in the team’s pecking order. Nashville is also a wild card team this year.

Victor Hedman – Defenseman – Tampa Bay Lightning

During the first of Tampa Bay’s back-to-back Stanley Cup championships in 2020 it was Hedman that was awarded the Conn Smythe Trophy, with 10 goals and 22 points in 25 games. Like the Caps and Preds, the Lightning are also a wild card team this year and have a tough postseason road ahead, plus Tampa Bay has other high-profile players that would be candidates including . . .

Andrei Vasilevskiy – Goaltender – Tampa Bay Lightning

Vasilevskiy was the Conn Smythe Trophy winner in 2021 as the Lightning won their second straight Stanley Cup, and after a sluggish stretch in his return from injury this past season he was solid down the stretch to guide Tampa Bay to a playoff berth. If the Lightning did win the Cup, Vasilevskiy and Hedman would have to contend with Nikita Kucherov and Steven Stamkos for Conn Smythe Trophy votes.

Cale Makar – Defenseman – Colorado Avalanche

Makar put up 29 points in 20 games in 2022 and was awarded the Conn Smythe Trophy as the Avalanche claimed the Stanley Cup. And the Avalanche put up 107 points this past season, and enter the postseason as one of the favorites on the Stanley Cup board. That leaves Makar as likely the best bet out of this group of seven to win a second Conn Smythe Trophy this spring, assuming of course that he could outshine high-scoring teammate Nathan MacKinnon in a championship run.

Jonathan Marchessault – Forward – Vegas Golden Knights

Finally, it was Marchessault that picked up the Conn Smythe Trophy last season as the Golden Knights won the Stanley Cup, after he put up 13 goals and 25 points in 22 games. Marchessault also had a team-high 42 goals and 69 points for the Golden Knights this past season, but a deep Vegas forward corps that includes Jack Eichel, Mark Stone, and Tomas Hertl could see anyone step up.