Conned Smythe – With the playoffs down to four teams, MISRYOUM’s list turns the Coned Smythe into a countdown of regret—revisiting trades that ended up shaping the Stanley Cup teams they helped build, and weighing who might deserve the award this year.
The playoffs are down to four teams. and the Coned Smythe countdown is back—one of the league’s most talked-about jokes dressed up as a serious premise. The award goes to the team that made the worst trade with the eventual Stanley Cup winner. based on how much that deal ends up mattering across the champion’s run.
Sometimes it’s obvious. Calgary Flames fans watched the Florida Panthers win with Matthew Tkachuk and Sam Bennett after those moves. In 2022. the Colorado Avalanche won the Cup and the Coned Smythe went to the Toronto Maple Leafs for handing them Nazem Kadri. But other years. the list of “wait. how did that work out?” trades is long enough to make the whole bracket feel like a trial.
So here are the ten teams in the best shape to win this year’s Coned Smythe—based on trades they made with the conference finalists still alive.
10. San Jose Sharks
The trades: The Sharks have a pair of former players in the Western Conference final thanks to 2024 trades, with Mackenzie Blackwood having been dealt to Colorado while Tomáš Hertl went to the Golden Knights in a mildly stunning deadline deal.
The case for: The Sharks are a long shot because neither guy has done much so far this postseason. But Hertl has been a game-breaker in the past. and he’s shown some signs of heating up recently. so maybe he goes on a spree. And Blackwood hasn’t had much action for the Avs, but could be one game away from a key role.
The case against: The resume just isn’t there so far, so they’re trailing most of the field.
Bottom line: There’s still time, but the Sharks better get swimming.
9. Colorado Avalanche
The trade: Three years ago, the Avalanche sent Alex Newhook to the Montreal Canadiens for two draft picks and Gianni Fairbrother.
The case for: While the deal made sense at the time and Newhook hadn’t exactly made the Avs regret it in the three years since. he’s suddenly emerged as a major story in this year’s postseason. With seven goals through two rounds. including the OT winner in Game 7 in Buffalo. Newhook might be gaining steam as an unexpected Conn Smythe candidate.
The case against: The Habs are still a long shot to win it all, and if they do, it will probably be because their big guns woke up and not because Newhook had to carry the load as he did against the Sabres.
Bottom line: In addition to the Patrick Roy callbacks, a Colorado/Montreal final would have some fun Conned Smythe implications; remember that the Avs got Artturi Lehkonen from the Habs back in 2022.
8. Ottawa Senators
The trade: Way back in 2019. the Senators sent Stone to Vegas for Erik Brännström. Oscar Lindberg and a second. While GM Pierre Dorion called it his proudest day as GM. critics weren’t quite as enthusiastic. and in hindsight. nothing Ottawa got back in this deal ended up helping its rebuild.
The case for: First things first — there’s the “no repeat winners” rule to prevent the upcoming Auston Matthews trade same deal from winning year after year. There was worry the Stone trade would have already been recognized when the Golden Knights won in 2023. But it wasn’t. because readers voted on that one and picked the Panthers handing Jonathan Marchessault to Vegas as that year’s winner.
The case against: While there’s no statute of limitations on the Conned Smythe, seven years feels like a long time to still be litigating the same trade, even one as lopsided as this one. Also, Stone is hurt right now and there’s no word on when (or even if) he might be back.
Bottom line: Wait, is the Conned Smythe like the Selke or Norris, where some guys win it as a lifetime achievement award? Are Dorion and the Senators due?
7. Chicago Blackhawks
The trades: The Blackhawks are a sneaky pick thanks to a pair of trades that had been overshadowed until recently. First, there’s the 2022 deal that sent Kirby Dach to the Canadiens for picks. And then there was their involvement in the Dallas/Carolina megadeal that featured Mikko Rantanen. That one saw the Hawks not only retain some salary but also send veteran Taylor Hall to the Hurricanes.
The case for: Dach has already had a fascinating postseason of ups and downs. and it feels like there are more twists to come. But the bigger name right now is Hall. who went from washed-up veteran to rootable OGWAC to one of the playoffs’ breakout stars. If the Hurricanes win it all. he wouldn’t be the favorite for the Conn Smythe — that would be Frederik Andersen — but he’d be in the conversation.
The case against: The Blackhawks got the Frank Nazar pick in the Dach trade, and Hall wasn’t doing much in Chicago, so the regret sting isn’t as sharp as it could be.
Bottom line: You don’t have to hate the trade you made to contend for a Conned, but it sure helps.
6. Buffalo Sabres
The trade: The Jack Eichel trade.
The case for: The Sabres drafted Eichel to be the franchise’s savior, got a few good seasons from him, saw the relationship crumble, then traded him to the Golden Knights for a decent but hardly breathtaking return. Now he’s the best player on one of the four teams left.
The case against: The Sabres were largely forced into the Eichel deal, making it because they had to, not because they thought it would make them better. And thanks to Alex Tuch emerging as a legitimate top-line star, this one doesn’t look as lopsided as it once did.
Bottom line: Watching Eichel lift the Cup would be painful for Sabres fans. But since they’ve already had to do it once, the sting doesn’t carry quite as much weight as it used to.
5. Nashville Predators
The trade: The Predators gave Scott Wedgewood to the Avalanche for Justus Annunen and a sixth.
The case for: Wedgewood has a good chance to be the starting goalie for the Stanley Cup champions.
The case against: Wedgewood is always one shaky game away from being replaced by Mackenzie Blackwood.
Bottom line: It could change quickly, but for now, Wedgewood has the Predators in solid contention.
4. New York Islanders
The trades: The Islanders helped stock the powerhouse Avalanche with a pair of trades. sending Devon Toews to Colorado for picks in 2020 and then last year’s Brock Nelson deadline deal. And Noah Dobson is also part of the broader picture. with the note that he hasn’t done a ton for the Habs yet in this year’s postseason but could emerge as a factor as he gets healthier.
The case for: Toews is a crucial piece of what the Avs have built, and Nelson had 30 goals this year. A Colorado championship would make the Islanders strong contenders.
The case against: While the Toews trade looked iffy at the time and downright awful today, the Nelson trade was a reasonable deadline seller move, and the Islanders got a nice haul for Dobson.
Bottom line: You could at least make a case that Toews is the most important Av to have been acquired by trade.
3. Calgary Flames
The trades: For the first time in three years. Flames fans don’t have to worry about Matthew Tkachuk and Sam Bennett in this column. But they’re still represented. having sent Nazem Kadri to the Avs at this year’s deadline while also supplying both halves of the Rasmus Andersson/Noah Hanifin pairing in Vegas.
The case for: Kadri’s already won the Cup in Colorado and could be about to do it again, while Andersson and Hanifin have been getting top-line minutes with Vegas.
The case against: Given how badly the Flames have been needing a rebuild, you could make a solid case that none of those three trades were bad, and in fact all three were win/win moves that teams like Calgary should be looking to make.
Bottom line: They’re in the running, but they’re not the favorites this time around.
2. Carolina Hurricanes
The trades: The original Mikko Rantanen trade saw them send both Martin Necas and Jack Drury to Colorado.
The case for: Necas had 100 points this season and is better than a point-per-game so far in the playoffs. Drury is also a key depth player who’s in the lineup every night.
The case against: Given how their side of the bracket is going, there’s not much sign they regret this trade.
Bottom line: After looming large on last year’s list, Rantanen is still casting a big shadow over this year’s version even though his team is out.
1. Dallas Stars
The trades: At last year’s deadline, the Stars sent Logan Stankoven and a pile of draft picks to the Hurricanes for Mikko Rantanen.
The case for: Rantanen’s heroics in last year’s playoffs had the Hurricanes looking like the Conned Smythe favorites. This year, Rantanen is sitting at home while Stankoven is part of arguably the postseason’s single best line, racking up offense with Taylor Hall and Seth Jarvis.
The case against: Was it a bad trade for Dallas? It’s doubtful the Stars would take a do-over today, even given how good Stankoven has looked lately. It’s possible all three of the teams in that Rantanen custody chain are happy with how it worked out.
Bottom line: Stankoven didn’t even score a goal in a few of Carolina’s games this spring.
Bonus team: Toronto Maple Leafs
The trades: They sent Nicolas Roy to the Avs for a first-round pick at this year’s deadline. but Roy hasn’t done enough to get the Leafs into consideration on that move alone. The bigger one here is the other Roy trade — where the Leafs did technically trade Mitch Marner to the Golden Knights in the hours before he would have left as a UFA anyway.
The case for: Marner might be the leading candidate for the Conn Smythe this year, and the Leafs did indeed trade him in a deal they clearly lost.
The case against: The Marner/Roy trade might not count as fully as the spirit of the award. It was more about a max-length contract extension, with a bit of old-fashioned blackmail (allegedly) rolled in. The argument here is that the Leafs taking a guy who’d clearly made up his mind to leave for nothing and turning him into Colorado’s first-round pick was actually solid work by Brad Treliving. If anything, giving the Leafs this year’s trophy goes against the spirit of the thing.
Bottom line: Against the spirit of the thing, maybe. But it’s also very funny. There’s also an added note: if Carolina wins, the Leafs also let Frederik Andersen walk as a free agent and gave the pick that turned into Seth Jarvis.
Honorable mentions: Anaheim (for Shea Theodore and Josh Manson), Pittsburgh (for Brett Kulak), Los Angeles (for Phillip Danault).
Conned Smythe Stanley Cup playoffs Dallas Stars Carolina Hurricanes Mikko Rantanen Logan Stankoven Taylor Hall Seth Jarvis Jack Drury Martin Necas Jack Eichel Alex Newhook