Which NHL team should win the 2025 Conned Smythe for worst trade with a contender?

New York Times

26-05-2025

With the conference finals well underway and the Stanley Cup Final looming, it's time to focus on the top candidates for the game's most important playoff award: the Conned Smythe.
Yes, that's 'Conned' and not 'Conn.' We all know about the Conn Smythe, given to the playoff MVP. But that's an individual award, and as we're constantly being reminded, hockey is a team game. And the Conned Smythe is a team award — specifically, the team that had the biggest impact on the playoffs by making the worst trade with a contending club.
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This is a fake award I invented a few years ago, and it's been retroactively awarded for every year of the cap era. The 2023 Vegas Golden Knights gave us a ton of strong candidates, and last year's field was competitive. You might be wondering if this year's contenders are just going to be a rehash of last year's list, given three of the four finalists are the same. But with plenty of big moves in the year since, some shifting dynamics among those teams and a 'no repeat winners' rule that I just made up to be nice to Sabres fans, there's plenty of turnover this year.
As always, these need to be player trades — no trading of future draft picks who turned into guys, and no waivers or free agency. We'll count down ten candidate teams, from weakest to strongest, based on how the field looks right now.
And yes, you think you know where this is going. But it's going to be a tougher call than you think.
The trades: The Habs sneak into the top ten with a couple of under-the-radar trades that are still in play. They get credit for the 2023 deal that sent Evgenii Dadonov to Dallas for Denis Gurianov, as well as the 2022 deal that sent Brett Kulak to Edmonton for William Lagesson, a 2022 second-round pick and a 2024 seventh-round pick.
The case for: While neither of those deals was a blockbuster, they ended with solid players in key roles on a contender, and one of those two is going to be in the Stanley Cup final. Given that Gurianov and Lagesson combined to play just 26 games for the Habs, they didn't get much in return other than that second-rounder.
The case against: Let's check to see who the Habs drafted with that second-round pick and OOPS, you know what, never mind.
Bottom line: Oh, lord, the Habs fans didn't even stick around for that section and are already down in the comments, aren't they?
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The trade: Spoiler alert: Mikko Rantanen is going to be the main character in this post. But trades go both ways, and right now, Logan Stankoven is having a decent run in Carolina.
The case for: It's not often you see a team trade away a 22-year-old stud in his first full season.
The case against: It's not often that guys like Rantanen are available, and right now, there's not a soul in Dallas who regrets this deal.
Bottom line: It would take a lot of weird stuff happening between now and the end of the final for this one to emerge as a true candidate. And let's just say Stankoven and the Hurricanes don't look like they'll be around to make it happen.
The trade: They sent Adam Henrique to the Oilers at last year's deadline.
The case for: He had the first two goals in the Oilers' series-turning Game 4 win against the Golden Knights.
The case against: The game made you go, 'Oh, neat, I guess Adam Henrique is on the Oilers.'
Bottom line: Barring an OT goal or two in the final, this one feels unlikely.
The trade: We love it when an old trade pops back up for Conned Smythe consideration. In this case, the Penguins can still claim credit for the 2012 deal that sent Jordan Staal to Carolina for a package of future assets that didn't pan out.
The case for: Staal isn't just a key piece of the Hurricanes — he's also their captain, meaning he'd be the one to take the Cup handoff from Gary Bettman. It feels like that would add some juice to the Penguins' case.
The case against: Lifting the Cup requires mixing in the occasional conference final win, so…
Bottom line: We'll just file this one under 'in case of miracle.'
The trades: The Sharks are our first team to have three trades in play, an impressive showing for a team that hasn't had a ton of veteran talent to work with recently. Two of those deals came around this year's deadline, with the Sharks sending Jake Walman to Edmonton and Mikael Granlund and Cody Ceci to Dallas, each deal landing them a first. And if we reach back a bit further, they also sent Brent Burns to the Hurricanes three years ago.
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The case for: The Sharks offer quantity and quality. Burns has been a key piece for the Hurricanes, not to mention the league's top OGWAC story. Walman has been a key addition to the Oilers' blue line. And Granlund has been one of the deadline's biggest impact players, including having a hat trick in a crucial 3-1 win against the Jets.
The case against: While those are all good players having legitimate impacts on this year's playoffs, were any of those trades bad for the Sharks? That's part of what the 'Conned' in Conned Smythe is supposed to mean, and I doubt the Sharks want a do-over on any of those deals. Burns was a salary dump, and Mike Grier added first-round picks in the other two moves.
If anything, you could argue that the Red Wings should get some Conned Smythe attention for sending Walman to San Jose in the first place. But the Sharks? They have no regrets.
Bottom line: I'm not saying it would be theoretically impossible to win the Conned Smythe on a trade that worked out for both sides, but the bar should be high. I don't think the Sharks come all that close to clearing it.
The trade: At the 2023 deadline, the Predators sent Mattias Ekholm to the Oilers for a first and some spare parts.
The case for: Ekholm has basically been a home run for the Oilers ever since the deal went down, slotting in as arguably their most important defenseman.
The case against: He's been hurt so far this postseason. While he's expected back soon, he won't have as much runway to make an impact as some other candidates. And Nashville fans probably don't mind this deal, since it landed them a strong prospect and some needed cap flexibility that allowed them to… well, on second thought, maybe they would mind.
Bottom line: Compared to the rest of the final four, the Oilers don't do much trading, so if they win the Cup then there won't be many options. (Then again, if Connor McDavid can win the Conn Smythe in a year where they lose in the final, maybe we can do the same with the Conned.)
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The trades: The Blackhawks were a key — if mostly forgotten — part of the Rantanen trade, even though they didn't know it at the time. But even if you don't want to give them any credit for retaining salary, don't forget that they also sent Taylor Hall of Carolina as part of that three-way deal.
And of course, they also sent Seth Jones to the Panthers at this year's deadline.
The case for: Jones has been very good in Florida, including a signature performance in Game 7 against Toronto.
The case against: Hall hasn't exactly lit up the scoreboard as part of Carolina's middle six. And given how Jones basically forced his way out of Chicago, you could argue that they didn't have much choice in moving him, which feels like it should hurt their Conned case.
Bottom line: One thing worth remembering that adds to the Hawks' case: A lot of us didn't love their side of the Rantanen/Hall deal, which saw them net only a third for Hall and all that retained salary. They even got an ultra-rare 'F' in our trade grades. That's the sort of whiff Conned Smythe voters love, so if Hall could catch fire with a few big goals, they'd have a shot.
The trades: The big one here is that the Bruins sent Brad Marchand to the Panthers at the deadline for a conditional second. But don't forget that they also sent Tyler Seguin to the Stars. Sure, it was over a decade ago, but for our purposes, it still counts.
(They also traded Trent Frederic to Edmonton at the deadline, although technically he had a stop in New Jersey as part of a three-way deal, so I'm not sure how much that counts.)
The case for: The Seguin deal was unquestionably bad, partly because the Bruins, for some reason, decided to film the discussions that led to it and then post that online. Time will tell if Boston fans view the Marchand deal as a negative, but seeing him go to a division rival and help them win a Cup would at least be tough to swallow.
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The case against: Because the Panthers are in the conference finals, that conditional second for Marchand is now a first, which lessens any sting Bruins fans might be feeling.
Bottom line: The bottom line here is that if you've never watched the Seguin trade video, you absolutely need to, because it will make you feel better about your own team's front office.
The trades: The Flames were a favorite for last year's award, thanks to the separate deals that sent Sam Bennett and later Matthew Tkachuk to the Panthers. They lost in a mild upset to the Sabres and their trio of Sam Reinhart, Brandon Montour and Kyle Okposo, but that may have just cleared the field for an easy win this year.
The case for: Bennett and Tkachuk are two of the Panthers' four or five most important forwards, and Bennett has been having the sort of greasy but effective postseason that's going to get him paid this summer.
The case against: Battling through an injury suffered at the 4 Nations, Tkachuk hasn't been anywhere near as visible in this year's postseason as he had in recent years.
Bottom line: The rare double-down of two stars traded to the same team makes the Flames the clear front-runner if the Panthers pull off the repeat.
The trades: It's obviously the Rantanen trade. But… which one?
That's the curveball we're being thrown here. The Conned Smythe isn't supposed to overlap with the Conn Smythe, but when the favorite for the latter has been traded that season, it should all add up to an easy call. Except in this case, 'traded' isn't specific enough, because it happened twice.
So which one do we use? The January shocker that sent him from Colorado to Carolina? Or the March deal that saw the Hurricanes flip him to Dallas?
The case for Colorado: Based on the admittedly loose set of rules around this completely made-up award, you could argue they shouldn't even be in the running. After all, they traded Rantanen to Carolina, and he doesn't play there anymore. He's not their Conned Smythe problem, any more than you'd blame the Predators or Blue Jackets for Seth Jones being a Panther.
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Except… well, this clearly isn't that, right? The Avalanche traded a superstar that they'd drafted and developed, apparently over a relatively small amount of money, in a move that stunned some teams around the league who didn't even know he was on the block. Then that same star showed up across the ice in the first round, and almost single-handedly ended their season just a few months later. If that kind of trade can't land you a Conned Smythe, what are we even doing here?
The case for Carolina: It's the Conned Smythe, not the Conned Smythe-once-removed. If Rantanen continues to dominate the postseason, the Hurricanes have a solid claim here under procedural grounds. And of course, if he were to cap off his run by beating the Hurricanes in the final, that makes the case all that much stronger. (But it doesn't seem like that's a realistic outcome anymore.)
The case against: If Rantanen wins the real Conn Smythe, there isn't one. But if the Stars lose to the Oilers, that would clear the field for someone else to move up and steal the prize.
Bottom line: I'm confused. If the Stars go to the final, and if Rantanen keeps dominating, then clearly one of these teams has to win. But which one? Do we stick to the letter of the law, or can we go with the spirit of the thing? Let me know what you're thinking in the comments, and we'll see if we can work this out.
(Top photo of Mikko Rantanen: Sam Hodde / Getty Images)