Jan 20, 2024; Boston, Massachusetts, USA; Former Boston Bruins Cam Neely walks onto the ice during a ceremony before before a game against the Montreal Canadiens at the TD Garden. Mandatory Credit: Brian Fluharty-USA TODAY Sports
10. Vancouver Canucks trade Cam Neely to the Boston Bruins (1986): Neely went on to have a Hall of Fame career in Boston
9. Washington Capitals trade Filip Forsberg to the Nashville Predators (2013)
Apr 16, 2025; Nashville, Tennessee, USA; Nashville Predators left wing Filip Forsberg (9) skates with the puck against the Dallas Stars during the third period at Bridgestone Arena. Mandatory Credit: Steve Roberts-Imagn Images
An awful deal for Washington as Forsberg has become Nashville’s all-time scoring leader
8. New York Islanders trade Zdeno Chara to the Ottawa Senators (2000)
Sep 28, 2005; Buffalo, NY, USA; Ottawa Senators defense Zdeno Chara (3) in action against the Buffalo Sabres at HSBC Arena. Credit: Lou Capozzola-USA TODAY NETWORK
Not only did the Islanders give up Chara in the deal, but they also gave up a first-round pick in the deal (Jason Spezza), who had an outstanding career
7. Calgary Flames trade Brett Hull to the St. Louis Blues (1988)
EAST RUTHERFORD, NJ – CIRCA 1988: Brett Hull #16 of the St. Louis Blues warms up prior to the start of an NHL Hockey game against the New Jersey Devils circa 1988 at the Brendan Byrne Arena in East Rutherford, New Jersey. Hulls playing career went from 1986-2005. (Photo by Focus on Sport/Getty Images)
Hull went on to have a Hall of Fame career with St. Louis, scoring 936 points
6. Montreal Canadiens trade Patrick Roy to the Colorado Avalanche (1995)
Canadian professional hockey player Patrick Roy of the Montreal Canadiens hoists the Stanley Cup over his head as he celebrates their championship victory over the Los Angeles Kings, Montreal, Canada, June 9, 1993. (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)
Roy went on to win two Stanley Cups with Colorado as Montreal fell to the bottom of the standings without him
5. Detroit Red Wings trade Marcel Dionne to the Los Angeles Kings (1975)
Jan 31, 1982, Los Angeles, CA, USA; FILE PHOTO; Los Angeles Kings center Marcel Dionne (16) during a game against the New York Rangers at the Great Western Forum. Mandatory Credit: Jayne Kamin-Oncea-USA TODAY Sports
Oft referred to as the best player never to win a Stanley Cup, Dionne thrived as one of the game’s best offensive players in Los Angeles.
4. New York Islanders trade Roberto Luongo and Olli Jokinen to the Florida Panthers (2000)
Choosing Rick DiPietro over Luongo was Islanders GM Mike Milbury’s biggest mistake
3. Boston Bruins trade Joe Thornton to the San Jose Sharks (2005)
Apr 10, 2006; Glendale, AZ, USA; San Jose Sharks center (19) Joe Thornton against the Phoenix Coyotes at Glendale Arena. Mandatory Credit: Rick Scuteri-USA TODAY Sports Copyright Rick Scuteri
Thornton left Boston to become a Shark and led the league in assists for the first three seasons after the trade
2. Edmonton Oilers trade Mark Messier to the New York Rangers (1991)
BOSTON, MA – MAY 24: Mark Messier #11 (right) of the Edmonton Oilers helps out teammate Joe Murphy drink from the Stanley Cup in the locker room as they celebrate their Game 5 win over the Boston Bruins on May 24, 1990 at the Boston Garden, Boston, Massachusetts. The Oilers defeated the Bruins 4-1 and won the Series 4 games to 1. (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)
Edmonton begins its dismantling trading “Mess” to the Rangers who went on to win its first Stanley Cup since 1940 just a few years later
1. Edmonton Oilers trade Wayne Gretzky to the Los Angeles Kings (1988)
EAST RUTHERFORD, NJ – NOVEMBER 11: Wayne Gretzky #99 of the Edmonton Oilers skates on the ice during an NHL game against the New Jersey Devils on November 11, 1982 at the Brendan Byrne Arena in East Rutherford, New Jersey. (Photo by B Bennett/Bruce Bennett Studios via Getty Images Studios/Getty Images)
Claiming financial hardship, Edmonton trades the “Great One” to the Kings, forever changing both teams’ fortunes
