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

With the conference finals well underway and the Stanley Cup final looming, it’s time to focus in 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 award that goes to the team that had the biggest impact on the playoffs by making the worst trade with a contending team.

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 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 basically just made up to be nice to Sabres fans, there’s actually plenty of turnover in this year’s candidates.

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.

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