There are four teams left in the playoffs, and that means the race for the informal Conned Smythe has narrowed too. The tongue-in-cheek award goes to the team that made the worst trade with the biggest impact on a season’s eventual Stanley Cup winner.
This year’s field is shaped by a familiar kind of regret. Calgary Flames fans watched the Florida Panthers win Stanley Cup titles with Matthew Tkachuk and Sam Bennett. The Colorado Avalanche won in 2022, and the Conned went to the Toronto Maple Leafs for handing them Nazem Kadri. That is the standard: one trade, one bruising outcome, one team left to wonder what might have been.
The current race has a sharp edge because it includes a franchise that knows the feeling too well. The Sharks have a pair of former players in the Western Conference final thanks to 2024 trades, after sending Mackenzie Blackwood to Colorado and Tomáš Hertl to the Golden Knights. Those moves now sit inside a postseason in which Colorado still has a live path and Vegas has been there before. The trade tree is the point. The teams in the bracket change, but the regret lingers.
Alex Newhook gives the story its most direct evidence. Three years ago, the Avalanche traded him to the Montreal Canadiens for two draft picks and Gianni Fairbrother, and Newhook has turned into one of the postseason’s better stories. He has seven goals through two rounds and scored the overtime winner in Game 7 in Buffalo, the kind of moment that makes an old trade look even worse in hindsight. One player leaves as a prospect package. Another arrives as a difference-maker when the games get tight.
The Senators have already lived through this kind of aftertaste. In 2019, Ottawa sent Mark Stone to Vegas for Erik Brännström, Oscar Lindberg and a second, and Pierre Dorion later called it his proudest day as GM. Critics were not nearly as enthusiastic. Nothing Ottawa got back ended up helping its rebuild, which is why the Stone deal finished second in a previous reader vote. Readers picked the Panthers handing Jonathan Marchessault to Vegas as that year’s winner, but Stone’s trade never drifted far from the conversation.
That is what makes the Conned Smythe such an odd and durable postseason exercise. It is not about the best team or the cleanest rebuild. It is about the trade that hangs over a champion’s spring, often years after the paperwork was filed. The list changes with every round, but the logic does not. A bad deal can survive front-office turnover, roster changes and even a parade. When the final four is set, the ledger gets clearer, not kinder.
