Which NHL Team Deserves the Conned Smythe Trophy for Worst Trade? Stanley Cup 2024 Edition (2026)

The Conned Smythe: A Trophy No Team Wants to Win

Every year, as the Stanley Cup Playoffs narrow down to the final contenders, there’s another, less celebrated award that hockey fans and analysts can’t help but debate: the Conned Smythe. No, it’s not an official NHL trophy, but it’s one of the most intriguing concepts in sports—a tongue-in-cheek honor for the team that made the worst trade, inadvertently handing a key piece to the eventual Stanley Cup champion.

Personally, I think the Conned Smythe is more than just a fun exercise; it’s a window into the high-stakes world of NHL trades, where one misstep can haunt a franchise for years. This year, with only four teams left in the playoffs, the race for this dubious distinction is heating up. Let’s dive into the contenders, but with a twist—I’ll be adding my own commentary, analysis, and a few hot takes along the way.

The Contenders: Who Made the Worst Move?

San Jose Sharks: The Long Shots

The Sharks traded Mackenzie Blackwood and Tomáš Hertl to the Colorado Avalanche and Vegas Golden Knights, respectively. On paper, it’s not a terrible look—both players are in the conference finals. But here’s the thing: neither has been a game-changer so far.

My Take: What makes this particularly fascinating is how the Sharks’ situation reflects the broader struggle of rebuilding teams. They’re not terrible candidates, but they’re also not making anyone regret the trades. It’s like they’re stuck in hockey purgatory—not bad enough to win the Conned Smythe, but not good enough to contend for the Cup. If you take a step back and think about it, this is the story of so many NHL franchises: stuck in the middle, neither sinking nor swimming.

Colorado Avalanche: The What-Ifs

Three years ago, the Avs traded Alex Newhook to the Montreal Canadiens. Fast forward to today, and Newhook is a playoff hero for the Habs. But here’s the kicker: the Avs got draft picks and Gianni Fairbrother in return.

My Take: One thing that immediately stands out is how this trade feels like a classic case of ‘what could have been.’ Newhook’s breakout is impressive, but the Avs aren’t exactly crying over spilled milk. What many people don’t realize is that trades like these often come down to timing. If the Avs had kept Newhook, would they still be contenders? Probably. But they also wouldn’t have the pieces they got in return. It’s a reminder that in the NHL, every move is a gamble.

Ottawa Senators: The Lifetime Achievement Award?

The Senators traded Mark Stone to Vegas in 2019 for a package that, in hindsight, was underwhelming. Stone has since become a cornerstone for the Golden Knights.

My Take: In my opinion, this trade is the poster child for the Conned Smythe. It’s been seven years, and Senators fans still wince when Stone’s name comes up. But here’s the twist: does it still sting enough to win this year? Personally, I think the Conned Smythe should have a statute of limitations. After a certain point, it’s less about the trade and more about the franchise’s inability to move on.

Chicago Blackhawks: The Sneaky Contenders

The Blackhawks traded Kirby Dach to Montreal and Taylor Hall to Carolina in separate deals. Both players are now making waves in the playoffs.

My Take: What this really suggests is that the Blackhawks are in a unique position. They’re not the favorites for the Conned Smythe, but they’re in the conversation because of the sheer volume of their trades. It’s like they’re playing the lottery—the more tickets you buy, the better your chances. But here’s the catch: none of these trades feel that bad. Sure, Dach and Hall are performing well, but the Blackhawks got decent returns. It’s a reminder that not every trade has to be a disaster to qualify for this award.

Buffalo Sabres: The Eichel Effect

The Sabres traded Jack Eichel to Vegas in a deal that felt forced at the time. Now, Eichel is a star for the Golden Knights.

My Take: A detail that I find especially interesting is how the Eichel trade is a case study in franchise mismanagement. The Sabres drafted him to be their savior, but the relationship soured, and they were left with no choice but to trade him. Watching Eichel succeed elsewhere is painful, but it’s also a lesson in the importance of player-team chemistry. What many people don’t realize is that sometimes, a trade isn’t just about the players—it’s about the culture and the fit.

Nashville Predators: The Goalie Gamble

The Predators traded Scott Wedgewood to Colorado, who is now in the running to be the starting goalie for the Cup champions.

My Take: From my perspective, this is a classic example of a trade that looks worse in hindsight. Wedgewood wasn’t a superstar in Nashville, but seeing him thrive elsewhere stings. It’s a reminder that goalies are the wild card in any trade—they can go from afterthought to hero in a single postseason.

New York Islanders: The Avalanche Pipeline

The Islanders traded Devon Toews and Brock Nelson to Colorado, both of whom have been key pieces for the Avs.

My Take: Personally, I think the Islanders’ situation is the most intriguing. Toews, in particular, has been a quietly crucial player for the Avs. But here’s the thing: the Islanders got decent returns in both trades. It’s a fine line between a bad trade and a necessary one. If you take a step back and think about it, this is the dilemma every GM faces: do you hold on to your stars or cash in for the future?

Calgary Flames: The Rebuild Blues

The Flames traded Nazem Kadri, Rasmus Andersson, and Noah Hanifin to Colorado and Vegas, respectively. All three are now key players for their new teams.

My Take: What makes this particularly fascinating is how the Flames’ situation reflects the challenges of rebuilding. On one hand, these trades were necessary to restock the cupboard. On the other, seeing these players succeed elsewhere is a bitter pill to swallow. It’s a reminder that sometimes, the Conned Smythe isn’t about a single bad trade—it’s about a series of moves that leave fans wondering, ‘What if?’

Carolina Hurricanes: The Rantanen Ripple Effect

The Hurricanes traded Martin Necas and Jack Drury to Colorado in the Mikko Rantanen deal. Both players are now thriving for the Avs.

My Take: In my opinion, this is the most underrated contender for the Conned Smythe. Necas and Drury aren’t just depth players—they’re impact players. But here’s the twist: the Hurricanes got Rantanen, who was a superstar for them. It’s a reminder that sometimes, even a ‘bad’ trade can work out in the end.

Dallas Stars: The Stankoven Surprise

The Stars traded Logan Stankoven to Carolina in the Rantanen deal. Stankoven is now a breakout star for the Hurricanes.

My Take: One thing that immediately stands out is how this trade feels like a perfect storm for the Conned Smythe. Stankoven is tearing it up, while Rantanen is sitting at home. But here’s the catch: the Stars aren’t exactly regretting the move. It’s a reminder that in the NHL, every trade has winners and losers—but sometimes, the lines are blurred.

The Bigger Picture: What the Conned Smythe Really Means

If you take a step back and think about it, the Conned Smythe isn’t just about bad trades—it’s about the stories behind them. It’s about the what-ifs, the missed opportunities, and the lessons learned. Personally, I think it’s one of the most human awards in sports because it’s not about perfection; it’s about the mistakes that make the game so compelling.

What this really suggests is that the NHL is a league where every move matters. A single trade can change a franchise’s trajectory, for better or worse. And while no team wants to win the Conned Smythe, it’s a reminder that in hockey, as in life, sometimes the biggest losses lead to the most interesting stories.

Final Thoughts

As we watch the final four teams battle it out for the Stanley Cup, let’s not forget the teams that made it possible—for better or worse. The Conned Smythe may not come with a trophy, but it comes with something just as valuable: a story. And in a league as unpredictable as the NHL, that’s worth more than any award.

So, who should win this year’s Conned Smythe? Personally, I’m leaning toward the Ottawa Senators. Seven years later, the Mark Stone trade still stings. But hey, that’s just my take. What’s yours?

Which NHL Team Deserves the Conned Smythe Trophy for Worst Trade? Stanley Cup 2024 Edition (2026)
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