The 10 Biggest In-Season Trades in NHL History – The Hockey Writers – Hockey History


When the Vancouver Canucks shocked the world by trading franchise defenseman Quinn Hughes during the season, it immediately reshaped the landscape of the NHL. Weeks later, many are still comprehending what just happened. Superstars are supposed to be untouchable and untradeable. But if we dig into NHL history, we’ll see that, as unbelievable as the Hughes trade was, it’s not unprecedented. We look at 10 of the rare, franchise-altering blockbuster deals that shook the league during the season.

As an additional note, we tried focusing on deals that did not occur around the NHL Trade Deadline. There were a couple we could not ignore, however. Nonetheless, these deals made waves (some continue to do so now) even if some had writing on the wall.

The 10 Biggest NHL Deals That Happened During the Season

Mikko Rantanen Traded Twice (From Avalanche to Hurricanes to Stars, 2025)

  • Avalanche to Hurricanes
    • Avalanche sent Mikko Rantanen
    • Hurricanes sent Martin Necas, Jack Drury, 2025 2nd-round pick, and 2026 4th-round pick (three-team deal)
  • Hurricanes to Stars
    • Hurricanes sent Mikko Rantanen
    • Stars sent Logan Stankoven, two first-round picks, and two third-round picks

Even in the cap era, this one felt unreal. Mikko Rantanen was a core piece of the Colorado Avalanche’s Stanley Cup-winning team. And yet they moved him in January to the Carolina Hurricanes. But after just 13 games with his new team, Rantanen was shipped again. This time, he was sent to the Dallas Stars (where he re-signed on a long-term deal). The trade made an immediate impact for both Colorado and Dallas, as Rantanen scored a hat trick to eliminate his former team in the first round of the playoffs.

Related: 20 Biggest NHL Trades in the Past Year

Bruins Dealt a Living Legend (From Bruins to Rangers, 1975)

  • Bruins sent Phil Esposito and Carol Vadnais
  • Rangers sent Brad Park, Jean Ratelle, and Joe Zanussi

Boston fans know what it’s like to deal legends to New York. Phil Esposito was the most prolific scorer of his time, and despite being 33 years old, was still putting up stats like Rookie mode on an NHL video game. The New York Rangers did not achieve much with Esposito, but neither did the Boston Bruins without him. The franchise entered a nearly 40-year Stanley Cup title drought and never had another Hart Trophy winner because…

Sharks Get an MVP in Joe Thornton (From Bruins to Sharks, 2005)

  • Bruins sent Joe Thornton
  • Sharks sent Marco Sturm, Brad Stuart, and Wayne Primeau

The trade that still doesn’t make sense. The Bruins traded their captain and star player in November, then watched “Jumbo” Joe Thornton explode into an MVP-caliber force in San Jose. The Sharks became instant contenders as Thornton helped them make deep playoff runs perennially. The Bruins spent years answering for it, though they would go on to win a Cup in 2011. This remains a benchmark for in-season shockers.

Joe Sakic Patrick Roy Colorado Avalanche
Joe Sakic and Patrick Roy of the Colorado Avalanche pose with the Stanley Cup. (Photo by Steve Babineau/NHLI via Getty Images)

Canadiens Ended Their Dynasty By Dealing Roy (From Canadiens to Avalanche, 1995)

  • Canadiens sent Patrick Roy and Mike Keane
  • Avalanche sent Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko

This remains one of the biggest “what-ifs” not just in Montreal Canadiens’ lore, but in NHL history. Patrick Roy’s exit from Montreal was abrupt and ugly. He butted heads with head coach Mario Tremblay, which culminated in a humiliating defeat (he allowed nine goals in a game), where he infamously told team president Ronald Corey that he was done with the franchise. Montreal’s tragedy became the Avalanche’s fortune as Roy immediately led his new team to a Stanley Cup (and another one a few years later) while the Canadiens have yet to win another (as of the 2024-25 season).

Flames Gift Gilmour to Toronto (From Flames to Maple Leafs, 1992)

  • Flames sent Doug Gilmour, Jamie Macoun, Kent Manderville, Ric Nattress, and Rick Wamsley
  • Maple Leafs sent Gary Leeman, Craig Berube, Michel Petit, Alexander Godynyuk, and Jeff Reese

Calgary Flames fans are familiar with letting superstars walk. Trading Doug Gilmour, who was becoming the team’s best player, is one that still stings in some fans’ minds. Gilmour arrived in Toronto and instantly became the soul of the franchise. He not only came close to winning the Hart Trophy as the league’s MVP, but was also one blown call away from leading the Leafs back to the Stanley Cup Final. To this day, many Leafs fans still see Gilmour as the franchise’s best player and/or captain.

Chelios Was Stunned When Chicago Dealt Him (From Blackhawks to Red Wings, 1999)

  • Blackhawks sent: Chris Chelios
  • Red Wings sent: Anders Eriksson, 1999 1st-round pick, and 2001 1st-round pick

This was one of the biggest NHL Trade Deadline deals at the time. Chris Chelios swore on his kids’ heads, via ESPN, that he did not ask to be dealt from the Blackhawks. Despite being an aging player (37 at the time), Chelios wanted to stay in Chicago. What made this all the more startling was who the Blackhawks dealt him to: the bitter rival Red Wings, who would go on to win two more Stanley Cup titles with Chelios.

Winnipeg Lost a Hero With the Selanne Deal (From Jets to Mighty Ducks, 1996)

  • Jets sent: Teemu Selanne, Marc Chouinard, and a 1996 4th‑round pick
  • Mighty Ducks sent: Oleg Tverdovsky, Chad Kilger, and a 1996 3rd‑round pick

The Winnipeg Jets trading Teemu Selanne is like the small-town version of the Edmonton Oilers trading Wayne Gretzky. The “Finnish Flash” took the NHL by storm, scoring 76 goals in his rookie season and capturing the hearts of the city. Unfortunately, the struggling small market forced ownership to make the hard choice. It just about broke every Winnipegger’s heart, including Selanne’s. Anaheim, on the other hand, paired Selanne with Paul Kariya to form one of the league’s hottest young duos, which led to the franchise’s eventual rise.

Thrashers Trade The Face of the Franchise (From Thrashers to Devils, 2010)

  • Thrashers sent: Ilya Kovalchuk, Anssi Salmela
  • Devils sent: Johnny Oduya, Niclas Bergfors, Patrice Cormier, 2010 1st-round pick, and 2010 2nd-round pick

Before a certain dude named “Alex Ovechkin”, Ilya Kovalchuk was the league’s sickest goal-scorer. He was also the face of the Atlanta Thrashers; thus, this deal all but put a nail in the franchise’s coffin. What’s more surprising here are the New Jersey Devils. They typically do not make blockbuster deals such as this. But with their new sniper, the Devils returned to the Stanley Cup Final, albeit in a losing cause.

An Olympic Snub Led to St. Louis’s Divorce (from Lightning to Rangers, 2014)

  • Lightning sent: Martin St. Louis
  • Rangers sent: Ryan Callahan, 2014 2nd-round pick, and 2015 1st-round pick (conditional)

Martin St. Louis was the heart and soul of the Tampa Bay Lightning for well over a decade, and it appeared he would retire with the team. However, Steve Yzerman, then-general manager of both the franchise and the Canadian men’s hockey team, originally snubbed him from the 2014 Olympic roster (he eventually got in as an injury replacement). Asking for a trade, Yzerman shipped him to the New York Rangers. The “Blueshirts” made a Stanley Cup Final run while the Lightning went on to form a new dynasty years later.

Martin St. Louis Tampa Bay Lightning
Martin St. Louis, Tampa Bay Lightning (Kim Klement-USA TODAY Sports)

Vegas Hits Jackpot on Eichel (From Sabres to Golden Knights, 2021)

  • Sabres sent: Jack Eichel, 2023 3rd-round pick
  • Golden Knights sent: Alex Tuch, Peyton Krebs, 2022 1st-round pick, and 2023 2nd-round pick

This was a slow burn that culminated in a blockbuster deal. Tensions between Jack Eichel and the Buffalo Sabres reached a boiling point in 2021 when the team refused to let him undergo surgery on a spinal disc herniation. This team stripped him of his captaincy and, within a few weeks, traded him to the Vegas Golden Knights. Eichel led the Golden Knights to their first Stanley Cup victory, while the Sabres, as of the 2024-25 season, still have the longest active playoff drought.

More Big Deals Along the Way?

In-season blockbuster trades are rare for a reason. Teams don’t usually part with franchise players once the season is underway, which is why deals like these still echo years later. Most of these deals weren’t just deadline business or cap dumps. They were destabilizing moves that forced organizations to redefine themselves on the fly. And as several front offices become bolder, it’s fair to wonder whether the next league-shaking in-season trade is closer than we think. In the NHL, no one is truly “untouchable”.

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