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Three of the Biggest NHL Trade Deadline Moves in History

Staff Writer 03/04/2025
5 Min Read
Regards of what the Toronto Maple Leafs may be thinking about Mitch Marner, they have to at least hold some extension talks with him.
Jan 18, 2024; Calgary, Alberta, CAN; Toronto Maple Leafs right wing Mitchell Marner (16) skates with the puck during the warmup period against the Calgary Flames at Scotiabank Saddledome. Mandatory Credit: Sergei Belski-USA TODAY Sports
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The NHL trade deadline, set for March 7, is a pivotal moment in the hockey calendar, where bold moves can redefine a team’s trajectory. Contending teams often use this opportunity to bolster their rosters, adding the missing pieces needed for a deep postseason run. Meanwhile, rebuilding franchises look to flip expiring contracts into valuable draft picks or prospects, setting the stage for future success.

The decision to buy, sell, or stand pat for teams on the playoff bubble can be agonizing, as it may dictate their immediate and long-term fortunes. These dynamics make the trade deadline a high-stakes chess match that captivates fans and reshapes Stanley Cup odds.

According to GameZinger.com, midseason trades profoundly impact betting markets and championship probabilities. A single acquisition can elevate a team’s status from dark horse to favorite or provide the depth needed to survive a grueling playoff series. For instance, top-tier teams like the Winnipeg Jets, Toronto Maple Leafs, and Vegas Golden Knights are already seen as strong contenders. However, no team is without small holes. A strategic addition could mean between advancing in the playoffs or being eliminated early. Conversely, sellers like the San Jose Sharks aim to maximize returns on veterans while building for the future.

Wayne Gretzky to the St. Louis Blues (1996)

If you know anything about hockey, you’ve heard about Wayne Gretzky. He’s likely the most prominent name the sport has ever seen, and his trade to the St. Louis Blues in 1996 was one of the more critical moments around the trade deadline. Gretzky requested to be traded after his former team, the Los Angeles Kings, went off track and wasn’t doing well financially. The Kings’ struggles went so far that players weren’t getting paid on time, so a player of Gretzky’s magnitude wasn’t suited for this situation.

The Canadian center was traded for Craig Johnson, Patrice Tardif, Roman Vopat, and two draft picks. His time in St. Louis didn’t do much for his legacy but paved the way for Gretzky’s final years in the NHL, which he spent in New York, playing for the Rangers.

Ray Bourque to the Colorado Avalanche (2000)

Ray Bourque was named to the All-Star team for 19 years straight. That says it all about the level of play he provided on the ice. However, one thing was missing throughout his career—the Stanley Cup. No matter what Bourque and the Bruins did and how well they performed during the entire season, they somehow fell short of winning the most important trophy.

Once the team started moving in the wrong direction, the always-loyal Ray Bourque changed his approach and expressed his desire to attempt to win a championship with another team. The defenseman went to the Colorado Avalanche in exchange for Brian Rolston, Martin Grenier, Samuel Pahlsson, and a first-round pick in one of the most legendary trades ever. This move was even more remarkable when Bourque won his first title in 2001, accomplishing his final goal in hockey.

Ilya Kovalchuk to the New Jersey Devils (2010)

The modern hockey era hasn’t seen many more groundbreaking trades than the one for Ilya Kovalchuk in 2010. Atlanta’s team was still competitive at the time and hoped to win the trophy. However, despite their history, Kovalchuk and the Thrashers couldn’t agree on a contract extension, and after two declined offers, the club’s front office decided to move on.

The Russian left wing was traded for Johnny Oduya, Niclas Bergfors, Patrice Cormier, and draft picks. This trade made Atlanta an immediate contender, eventually leading to a Stanley Cup Final appearance in 2012. Unfortunately, Kovalchuk couldn’t win another trophy in the NHL. He left when the 2012 NHL lockout started and decided to retire from the league in 2013. Ilya continued to play in the KHL until 2018, when he announced his return to the NHL.

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