5 biggest NHL in-season trades of all-time ft. Mikko Rantanen, Joe Thornton & more

The Mikko Rantanen trade has hit the NHL like a nuclear blast. The swap between the Colorado Avalanche and the Carolina Hurricanes (with the Chicago Blackhawks as brokers) has led to discussion of it as one of the biggest in-season trades ever.

So, here’s a look at the five biggest in-season trades of all time.

5 biggest in-season trades of all-time featuring Mikko Rantanen

#5 Wayne Gretzky to St. Louis Blues, 1996

Wayne Gretzky in action for the St. Louis Blues during an NHL game. (Credits: Getty)

As the 1996 trade deadline approached, the LA Kings dealt soon-to-be free agent Wayne Gretzky to the St. Louis Blues in exchange for a package that included first and fifth-round draft picks, along with players Craig Johnson, Patrice Tardif and Roman Vopat.

The deal paid off for the Blues, as Gretzky led them to the playoffs despite a lackluster record. However, St. Louis lost to the Detroit Red Wings in the playoffs. Gretzky left during the offseason to join the New York Rangers.

The trade is still considered among, if not the biggest, in Blues history.

#4 Patrick Roy to Colorado Avalanche, 1995

Montreal Canadiens franchise goaltender Patrick Roy was fed up with team management. The standoff was highlighted when then-coach Mario Tremblay humiliated Roy by leaving him in goal following a nine-goal shellacking at the hands of the Detroit Red Wings on December 2, 1995.

Roy was finally pulled from the game and walked into the tunnel, never returning to the ice for the Habs. Days later, the Hall of Famer was traded to the Colorado Avalanche along with Mike Keane for netminders Jocelyn Thibault, Andrei Kovalenko and Martin Rucinsky.

The Avalanche would win the Stanley Cup that season with Roy in the crease.

#3 Doug Gilmour to Toronto Maple Leafs in 10-player swap, 1991

Doug Gilmour #93 in action for the Toronto Maple Leafs during an NHL game. (Credits: Getty)

In January 1991, a disgruntled Calgary Flames center, Doug Gilmour, left the team to join Team Canada in protest over a contract dispute. Days later, the Flames worked out a 10-player swap, sending Gilmour to the Toronto Maple Leafs for Gary Leeman as the central piece in return.

Leeman, a former 50-goal scorer, didn’t succeed in Calgary. Meanwhile, Gilmour was the heart and soul of the Leafs, leading them to back-to-back Conference Finals appearances in the early 1990s. The deal remains the largest trade in terms of players involved.

#2 Joe Thornton to San Jose Sharks, 2005

The Boston Bruins traded their captain, Joe Thornton, in 2005 amid an effort to shake up a struggling team. The Bruins sent Jumbo Joe, the 1997 first-overall pick, to the San Jose Sharks in exchange for Marco Sturm, Wayne Primeau and Brad Stuart.

Thornton led the Sharks to several successful playoff runs, but the team failed to reach the Stanley Cup Final.

#1 Mikko Rantanen to Carolina Hurricanes in three-player trade, 2025

In late January 2025, the Colorado Avalanche ended months of speculation by shipping 100-point winger Mikko Rantanen to the Carolina Hurricanes in exchange for Martin Necas, Jack Drury, and draft picks.

The trade involved a swap of skilled wingers Mikko Rantanen and Martin Necas, dealing with contract issues that may resolve concerns for each team. While it’s too early to declare a winner, initial signs suggest Mikko Rantanen could be the most valuable acquisition in recent history.