Which NHL team should win the Conned Smythe for worst trade with the Stanley Cup winner?

We’re down to four teams left in the playoffs, and longtime readers know what that means: It’s time to take a look at the field for one of the league’s most prestigious awards, the Conned Smythe.

Yes, Conned. If you’re new to the concept, the Conned Smythe goes to the team that made the worst trade that had the biggest impact on each season’s eventual champion. Sometimes it’s a relatively obvious call, such as when Calgary Flames fans watched the Florida Panthers win Stanley Cup titles with Matthew Tkachuk and Sam Bennett, or when the Colorado Avalanche won in 2022 and the Conned went to the Toronto Maple Leafs for handing them Nazem Kadri. In other years, there are almost too many candidates for a given team.

We want to avoid feeling overwhelmed, so it’s smart to get organized now. Here are the ten teams that are in the best shape to win this year’s Conned Smythe, based on the trades they made with the conference finalists.

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 — we’ve always had an informal “no repeat winners” rule to prevent the upcoming Auston Matthews trade same deal from winning year after year, and I was worried the Stone trade would have already been recognized when the Golden Knights won in 2023. But no, we let you readers vote on that one, and you picked the Panthers handing Jonathan Marchessault to Vegas as that year’s winner.

The Stone trade finished second, though, so by process of elimination, it’s a strong candidate here, assuming Stone can get healthy.

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 we don’t know 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? I may need to reflect on this.

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 we’re missing that sting of regret that elevates a good Conned Smythe story into a great one.

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: Sorry Sabres fans, I know you’re already hurting, but we have to include the Jack Eichel trade.

The case for: You know the drill by now. The Sabres drafted Eichel to be the franchise’s savior, got a few good seasons from him, saw the relationship crumble and 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. Some of that is on them, obviously, but it’s worth considering. 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, I’m not sure this one carries quite as much weight as it used to.

5. Nashville Predators

The trade: Remember when the Avalanche had no goalies, and it was the only thing that was keeping them from becoming a powerhouse? Luckily for all of us, the Predators stepped up and gave them Scott Wedgewood for Justus Annunen and a sixth.

The case for: Wedgewood has a good chance to be the starting goalie for the Stanley Cup champions. That feels important. Ah well, at least the Predators don’t need a guy like him because Juuse Saros will be good forever.

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 don’t forget Noah Dobson, who 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 sneakily 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 perfectly reasonable deadline seller move, and they 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 well-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 the sort of 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. That’s progress, right?

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. Meanwhile, Drury is a key depth player who’s in the lineup every night.

The case against: Given how their side of the bracket is going, I’m not sure the Hurricanes regret this trade all that much.

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. In fact, let’s talk about him again …

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 our old pal Mikko Rantanen.

The case for: Rantanen’s heroics in last year’s playoffs had the Hurricanes looking like the Conned Smythe favorites, so fair’s fair. 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? Put it this way, I doubt they’d 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. What a bum.

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 he hasn’t done enough to get the Leafs into consideration on that move alone. No, the big one here is the other Roy trade — the one 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: I’m not really sure what to do with the Leafs. On the one hand, 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: But does that really count? The Marner/Roy trade was really more about a max-length contract extension, with a bit of old-fashioned blackmail (allegedly) rolled in. If anything, 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 a rare bit of solid work by Brad Treliving. It feels like it would go against the spirit of the thing to give the Leafs this year’s trophy.

Bottom line: Against the spirit of the thing, maybe. But also very funny, and that tends to be the tie-breaker around here. (And while neither decision counts for our purposes, if Carolina wins, then don’t forget the Leafs also let Frederik Andersen walk as a free agent and gave them 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).