
The Unofficial Award for the Most Regrettable Trade: The Conned Smythe
As the NHL playoffs reach a fever pitch and we narrow the field down to the final four contenders, it is time to discuss one of the league’s most prestigious—albeit entirely fictional—honours: The Conned Smythe.
For the uninitiated, the Conned Smythe isn’t about individual brilliance on the ice. Instead, it is awarded to the team that made the absolute worst trade, providing a massive boost to the eventual Stanley Cup winners. Whether it’s a deadline panic or a long-term rebuild gone wrong, the Conned Smythe celebrates the art of the ‘trade regret’.
From the Florida Panthers benefiting from Calgary’s losses to the Colorado Avalanche thriving on Toronto’s mistakes, the history of this award is rich with irony. As we look at the current finalists, here are the top candidates for this year’s trophy.
The Top Candidates for the Conned Smythe
Who is most likely to accidentally hand over the championship? Let’s break down the most suspicious trades involving this year’s contenders.
- The San Jose Sharks: With Tomáš Hertl in Vegas and Mackenzie Blackwood in Colorado, the Sharks have assets on both sides of the final. While they haven’t dominated yet, Hertl’s ability to be a game-changer makes San Jose a dark horse for the award.
- The Montreal Canadiens: The trade of Alex Newhook to the Avalanche is starting to sting. Newhook has emerged as a postseason powerhouse, scoring seven goals through two rounds. If Colorado lifts the Cup, Montreal’s management might be feeling the heat.
- The Ottawa Senators: The Mark Stone trade to Vegas is a classic case of long-term regret. While it happened years ago, the lack of return for a superstar like Stone continues to haunt Ottawa, especially if Stone returns to lead Vegas to victory.
- The Buffalo Sabres: The Jack Eichel saga is legendary. Seeing Eichel as the best player on a championship-bound team is a nightmare scenario for Buffalo fans, even if the trade was practically forced.
- The Toronto Maple Leafs: Between the Mitch Marner situation and the Nazem Kadri history, the Leafs are perennial candidates. Trading Marner to the Golden Knights—even under complex circumstances—could be the ultimate ‘Conned’ move if Vegas wins it all.
The ‘Sneaky’ Contenders
Not every bad trade is a blockbuster. Some are subtle contributions that solidify a championship roster.
Take the Nashville Predators, who sent Scott Wedgewood to Colorado for a pittance. Wedgewood could easily end up as the starting goalie for the champions. Similarly, the New York Islanders helped build the Avalanche powerhouse by sending Devon Toews and Brock Nelson their way.
Even the Calgary Flames are in the mix. While they’ve moved on from the Tkachuk era, sending Nazem Kadri to Colorado and a defensive pairing to Vegas means they are effectively rooting against two different finalists.
Final Verdict: Who Wins the Regret?
While the Stanley Cup winners will celebrate with champagne, the Conned Smythe winner will be left staring at their trade history with a sigh. Whether it’s the long-term failure of the Senators or the immediate impact of the Canadiens’ loss of Newhook, the drama off the ice is just as compelling as the action on it.
To stay updated on the latest NHL standings and playoff brackets, keep a close eye on the rosters. The more a former player dominates, the closer their old team gets to the trophy of regret.
Who do you think deserves the Conned Smythe this year? Let us know in the comments!




