Ranking the Last 10 Conn Smythe Winners

The Conn Smythe Trophy is perhaps the most sought-after individual award in the NHL, as the player awarded with it usually gets to hoist the Stanley Cup a few minutes later.

Well, usually…

With the award going to Jordan Staal for his Stanley Cup-winning run in 2026, we thought it would be interesting to rank the last ten Conn Smythe-winning campaigns, from worst to first.

Jordan Staal, 2026

It feels wrong to put this win in last place, because Staal definitely deserves to be celebrated. He has spent 14 seasons with the Carolina Hurricanes, experiencing many highs and lows, from campaigns that ended in high draft lottery odds to conference finals appearances.

If this were a Stanley Cup Final MVP, Staal would be placed higher. He scored in the first five games of the Final, including a highlight-reel falling-down goal in Game 4. Staal finished with eight goals and 12 points in 19 playoff games, which, while impressive, isn’t quite up there scoring-wise with the other forward Conn Smythe wins of the last ten years. Major props do have to be given for his defensive impact, though, as he won plenty of clutch defensive zone faceoffs and killed penalties for the Hurricanes.

Jonathan Marchessault, 2023

If this list were strictly narrative-based, Jonathan Marchessault would be near the top. He was one of the original expansion draft Vegas Golden Knights, part of the “Golden Misfits” group of players undervalued by their previous teams. Marchessault was an immediate impact player in the Golden Knights’ first run to the Final, leading his team in goal scoring with eight.

In their 2023 Stanley Cup run, Marchessault again led the Golden Knights in goals and was second in points to Jack Eichel. Three of these goals were game winners, which showcase Marchessault’s clutch nature. He slots in at number 9, as while he scored goals in bunches, the Conn Smythe very well could have gone to his linemate, Eichel, whose 200-foot game and playmaking ability were the difference that finally got Vegas over the hump.

Sam Bennett, 2025

He may not be the most popular Conn Smythe winner, especially amongst fans of the team the Florida Panthers have faced in the playoffs, but Sam Bennett definitely deserved the trophy.

The grinding forward has always had a knack for finding the net in the postseason. Even in his early years with the Calgary Flames, he often stepped up when the team needed him. He reached another gear in Florida, however, and the 2025 Stanley Cup Final was his masterpiece. He scored 15 goals in the playoffs, becoming the fourth active player to do so after Alex Ovechkin, Sidney Crosby, and Zach Hyman. He also had seven assists, bringing his point total to 22. The knock against Bennett is that, despite an excellent playoff run, several other players could’ve won the hardware. Brad Marchand was exceptionally clutch while Carter Verhaeghe, Matthew Tkachuk, and Sam Reinhart all tied for the team lead in points with 23. It took a village to win this Stanley Cup.

Ryan O’Reilly, 2019

Winning the Stanley Cup and Conn Smythe was quite the way to cap off a dream season for Ryan O’Reilly, who joined the St. Louis Blues that previous offseason. The Blues struggled in O’Reilly’s first few months with the team, but went on a historic tear in the second half, with O’Reilly clearly driving that with a Selke Trophy-winning campaign.

O’Reilly did not slow down in the playoffs, scoring eight goals and 23 points in 26 playoff games. Five of these goals came in the brutal seven-game Stanley Cup Final against the Boston Bruins, including a goal and an assist in Game 7. O’Reilly kept up his great defense in the series, often going head-to-head against Patrice Bergeron’s “perfection line” and somehow winning plenty of those minutes. Some may say that rookie goalie sensation Jordan Binnington deserved the award, but O’Reilly was consistency personified and finally had a scoring explosion when it mattered most.

Sidney Crosby, 2017

The only multi-time Conn Smythe winner on this list, Sidney Crosby, had previously won the award in the 2016 Stanley Cup Playoffs. That Pittsburgh Penguins team was particularly stacked, and thus, many players like Phil Kessel, Matt Murray, or Kris Letang could’ve been named playoff MVP.

In the 2017 Stanley Cup Playoffs, Crosby proved that he was still the engine that drove the team. While Evgeni Malkin led the Penguins in points, Crosby outscored him at even strength and had a better points-per-game mark due to being sidelined a game with a concussion. Crosby was also at his best defensively, routinely matching up against the other teams’ stars and winning his matchups.

Alex Ovechkin, 2018

It took him 13 seasons, but at long last, Alex Ovechkin was a Stanley Cup champion. Not just that, either, he also took home the Conn Smythe Trophy, playing possessed throughout his entire playoff run.

The Washington Capitals had some notably deeper rosters in previous playoff runs, as they lost key depth pieces like Karl Alzner, Marcus Johansson, and Kevin Shattenkirk before the 2017-18 season. The dominance of Ovechkin proved to be the difference, as he scored 15 goals in the 2018 Playoffs, the most in a single playoff run since Crosby in 2009. The only reason he isn’t higher is that while dominant, linemate Evgeny Kuznetsov led the team in points with 32.

Victor Hedman, 2020

This might be the most underrated Conn Smythe win in quite some time. The Tampa Bay Lightning squad was filled with elite talent that really showed up in the 2020 Playoffs that took place in the Toronto and Edmonton “bubbles”. 

Hedman’s status in these playoffs actually seemed to be up in the air, as he injured his ankle in a seeding round match against the Philadelphia Flyers. He was locked and loaded and ready to go for Game 1 against the Columbus Blue Jackets, though, playing over 57 minutes of the game, which went to a fifth overtime. Hedman scored a whopping 10 goals, including a clutch double-overtime winner to send the Presidents’ Trophy-winning Bruins home in the second round. He finished the postseason with 22 points as well, an impressive total for a player who also played shutdown defense.

Cale Makar, 2022

While Hedman’s Conn Smythe campaign comes close, Cale Makar’s 2022 Playoffs were the greatest by a defenseman in a long time. The Colorado Avalanche were an unstoppable force in those playoffs, only losing four games total. They went up against an immovable object in the defending Cup champions, the Lightning, and still clobbered them. 

While the Avalanche had a plethora of star talents like Nathan MacKinnon, Mikko Rantanen, and Gabriel Landeskog, Makar was the difference. He scored eight goals and 21 assists for 29 points as a member of the Avs’ blue line corps. His shifty skating and powerful shot proved too much for teams, as he dominated every single series. A highlight of the run was a five-point night to secure a Western Conference victory over the Edmonton Oilers.

Connor McDavid, 2024

Connor McDavid’s Conn Smythe win was historic, as he became the first player since Jean-Sébastien Giguère in 2003 to win the Conn Smythe as a member of the losing team. Fans were confused, boos were loud, ESPN talking heads were upset, but at the end of the day, one can’t deny this was a legendary run.

McDavid put up eight goals and 34 assists for a total of 42 points in the playoff run. This was the most assists ever in a single playoff campaign, and was the most points in one since Mario Lemieux in 1991. When the Oilers went down 3-0 to the Panthers, he answered with back-to-back four-point games to make it a series. While his Oilers were ultimately unable to knock off the Panthers and win the Stanley Cup, his run was so historic that voters had no choice but to honor him with the Conn Smythe.

Andrei Vasilevskiy, 2021

Surprisingly, there’s only been one goaltender to win the Conn Smythe in the last 10 seasons, as perhaps he set the bar too high? Even on a Lightning team that saw Brayden Point score 14 goals and Nikita Kucherov tally 32 points, it was clear that Vasilevskiy was their best player.

Perhaps the most impressive aspect of Vasilevskiy’s incredible 2021 Playoff run was how clutch he was. He had a shutout in every single clinching game. This extended Vasilevskiy to a five-game series clincher shutout streak if you include the 2020 Playoffs. Per MoneyPuck’s goals saved above expected stat, Vasilevskiy had a record-breaking total of 26.6. The only other time a goalie has eclipsed 20 in a playoff run in that stat besides Vasilevskiy in 2021 was Vasy himself in 2020, when he had 20.8. In terms of the more well-known stats, he finished the playoffs with a .937 save percentage and a 1.90 goals-against average.

Who’s Next?

With the Stanley Cup and the Conn Smythe just being awarded a few days ago, we will have to wait about a year until we find out the next winner of this award. With that said, the last 10 winners showcase that it can go to a variety of players, from the legends in the pantheon of their position to the depth pieces who come in clutch in the big moments.