Ranking the top 5 worst Conn Smythe Trophy winners in NHL history

Not every Conn Smythe Trophy winner in NHL history was deserving.

Every year, the NHL awards the Conn Smythe Trophy to its playoff MVP. In many ways, hockey’s the only sport that gets it right. The NBA, NFL, and MLB all only give out MVP awards for their respective championships instead of the entire postseason. Hockey, though, rewards a player’s entire postseason resume, instead of just a small (but important) blip of it.

That said, like every award, the Conn Smythe Trophy isn’t always awarded to the right player. Voters are human. They screw up. We all do because we’re human and we’re flawed.

This year’s Conn Smythe Trophy race will likely be won by Victor Hedman. Nikita Kucherov and Brayden Point would be deserving winners as well. Should the Dallas Stars come back from their 2-1 deficit and win the Stanley Cup, it will likely go to either Miro Heiskanen or Anton Khudobin. Whoever wins it this year likely won’t be facing too much controversy.

With the Stanley Cup Playoffs wrapping up soon, here’s a look at the five least deserving Conn Smythe Trophy winners of all-time. I like to be transparent, so let me explain my process. I’m strictly looking at players who shouldn’t have won it. Not necessarily “the worst” winners, but the “least deserving” winners.

Before I begin, let me just say that, no, you’re not going to find Jean-Sebastian Giguere or Ron Hextall on this list. They were both objectively the best players in 2003 and 1987, respectively. Plus the award doesn’t have to go to a player on the winning team.

Honorable Mentions

Everyone talks about how Phil Kessel should have won the Conn Smythe in 2016 over Sidney Crosby. They’re right, but it’s not like Crosby was a bum that postseason. Still, Kessel should have won because he led the “HBK” line and there’s a zero percent chance the Penguins win the Stanley Cup without their famous third line.

Dominik Hasek of the Buffalo Sabres probably should have won it in 1999. He was the biggest reason why the Sabres were even in the Stanley Cup Final to begin with. And he was great during the Stanley Cup Final. The Stars lacked an obvious choice for the Conn Smythe, so had Hasek won it, I wouldn’t have had any issues.

Mark Messier’s 1984 Conn Smythe was the last one left off this list. Here’s why. Yes, Wayne Gretzky should have won the Conn Smythe in 1984. But at least Messier was still pretty darn good during that postseason. I don’t agree with the pick, but I can at least understand the logic behind it.