When Wayne Gretzky was traded back in 1988, it proved that anybody in the NHL could be had if the price was right. Some of the game’s most established stars have swapped teams in the past because there’s been so much demand for them. In addition, some players such as Brett Hull, Bernie Parent, Dominik Hasek, and Tony Esposito didn’t really flourish and become fan favourites until after their first trades. Others such as Dave Keon, Bobby Hull, and Gordie Howe jumped ship to the WHA (World Hockey Association) before returning to the NHL and some including Bobby Orr and Borje Salming broke the hearts of their team’s fans by signing as free agents with other teams.

On the flip side of the coin, players such as Maurice Richard, Mario Lemieux, Steve Yzerman, and Jean Beliveau played their entire careers with one club. Below is a list of 15 players who were involved in some of the most heartbreaking trades in NHL history. Some of them ended up in the Hall of Fame and others were simply hard workers or skilled scorers. The one thing they all have in common is that they were fan favourites and their supporters were devastated when they were traded. Oddly enough, many of these players were dealt more than once during their careers.

15. P.K. Subban

Gary A. Vasquez-USA TODAY Sports

Gary A. Vasquez-USA TODAY Sports

The most recent entry to this list is the P.K. Subban to Nashville trade, with Montreal picking up All Star defenceman Shea Weber in return. This deal had many Habs fans in tears, but let’s not forget there are some Predators’ supporters who aren’t too happy about it either. Both Subban and Weber are elite NHL defencemen who know how to put the puck in the net and setup their teammates, especially on the power play. However, their personalities are quite different. Subban is a somewhat cocky and arrogant character with a bubbly, positive attitude whereas Weber is more reserved. Subban is seen as a chance taker on the ice and who can forget his generous charity work. Habs’ fans also like to point out that Subban is three years younger than Weber and even though he makes more per season, Weber is under contract until he’s 40 due to a mind-boggling 14-year, $110 million contract.

14. Darryl Sittler

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

Centre Darryl Sittler was the Maple Leafs captain and leader in the 1970s after being drafted eighth overall in 1970. By 1972-73, Sittler was already one of the top players in the league. He reached the 100-point barrier twice and also had seasons of 90, 96, and 97 points. Sittler was the heart and soul of the Leafs and set an all-time record with 10 points in a game in 1976. Things turned sour when Punch Imlach returned to Toronto as GM in 1979 and tried to undermine the captain’s power. Things got so bad that Sittler took the C of his sweater and owner Harold Ballard called him a cancer. Sittler and Ballard eventually made up and the C was back on his chest, but the damage was done. Imlach was reportedly offered Rick MacLeish and Andre Dupont for Sittler, but the Leafs idol and Hall of Famer was eventually traded to Philly in 1982 in one of the NHL’s worst-ever trades for Rich Costello and a second-round draft pick. Sittler scored 916 points in 844 games with Toronto and added 178 points with the Flyers before being dealt again to Detroit. He totaled 27 points in 61 outings with the Wings before retiring.

13. Lanny McDonald

via zimbio.com

via zimbio.com

The Lanny McDonald trade from Toronto ties in with the Sittler deal. Right-winger McDonald and Sittler were line mates, best of friends, and had great chemistry together on the ice. McDonald was drafted fourth overall in 1973 and quickly became a fan favourite with 74 points in his first 134 games and then breaking out with a 93-point season in 1975-76. The mustachioed one scored four-straight 40 goal seasons, but was suddenly dealt by Punch Imlach to the Colorado Rockies just four days after Christmas in 1979. The Leafs sent McDonald and promising defenceman Joel Quenneville west for forwards Pat Hickey and Wilf Paiement. Toronto received a couple of good players in the deal, but Leafs fans and players were heartbroken as Imlach appeared to make the trade simply to spite Sittler. McDonald was traded once more from the Rockies to Calgary where he won a Stanley Cup. He finished his career with 500 goals and 506 assists in 1,011 games and is a Hall of Famer.

12. Jarome Iginla

Isaiah J. Downing-USA TODAY Sports

Isaiah J. Downing-USA TODAY Sports

Right-winger Jarome Iginla was drafted 11th overall by Dallas in 1995, but traded to Calgary before playing a game with the Stars. It was Iginla’s second trade that soured the fans though when the Flames more or less gave him to Pittsburgh on March 28, 2013 for Ben Hankowski, Kenny Agostino, and a first-round draft choice, which became Morgan Klimchuk. All Iginla did in Calgary was become the team’s leader and captain who scored 525 goals and 575 assists for 1,095 points in 1,219 games. Iginla was the heart of the Flames and was as happy dropping the gloves as scoring a goal. He won an Art Ross Trophy as well as a pair of Maurice Richard Awards, was named to the All-Rookie Team, and made six All-Star squads. Iginla had 11 straight seasons with at least 30 goals, scored at least 21 three other times and hit the 50-goal mark twice. Iginla leads the Flames in all-time games, goals, and points and it’s easy to see why fans were devastated when the now 39-year-old was dealt, especially since he’s scored 86 goals in 242 games since leaving.

11. Ray Bourque

Bob DeChiara-USA TODAY Sports

Bob DeChiara-USA TODAY Sports

Ray Bourque leads all NHL defencemen in several all-time career scoring categories simply because he’s one of the best ever to patrol the blue line. Bourque was drafted eighth overall by Boston in 1979 and played 20 straight years with the Bruins. He holds all sorts of team records and milestones and won numerous trophies, but was never lucky enough to win a Stanley Cup in Beantown. Bourque was traded to the Colorado Avalanche along with Dave Andreychuk in return for Brian Rolston, Samuel Pahlsson, Martin Grenier, and a first-round draft pick in March of 2000. Some fans believed the Bruins were doing Bourque a favour as he was able to win a Stanley Cup two years later, but others thought it was sacrilege to send a Boston legend packing after a two-decade career with their team. Bourque promptly retired shortly after skating around the rink with the Stanley Cup in 2001.

10. Dave Andreychuk

via thehockeywriters.com

via thehockeywriters.com

Left-winger Dave Andreychuk is one of several players on this list who was traded more than once and the fans felt it each time. He’s a former Buffalo first-round draft pick of 1982 who was a two-time All-Star and captained a Stanley Cup winner in Tampa. Andreychuk was an extremely underrated player whose numbers should put him in the Hall of Fame. He scored 640 goals and added 698 assists for 1,338 points in 1,639 games and is the NHL leader in power play goals with 274. Andreychuk also played with New Jersey, Tampa, Toronto, Boston, and Colorado and added 97 points in 162 playoff games. He was one of the most consistent scorers in history and fans in Buffalo and Toronto were extremely saddened when he was dealt. Buffalo traded him after 10 seasons and 804 points in 837 games to Toronto in 1993 with goaltender Darren Puppa and a first-round draft choice for Grant Fuhr and a fifth-round draft choice. Andreychuk then scored 219 points in 223 games with Toronto before being traded to New Jersey for a second and third-round draft choice in 1996. Both trades upset fans and rightly so.

9. Grant Fuhr

via nhl.com

via nhl.com

At 5-foot-10 and arguably overweight at 201 lbs, Grant Fuhr wasn’t the prototypical goaltender. But his competiveness and athleticism helped Edmonton win four Stanley Cups. Fuhr is a Hall of Famer who was named to six All-Star teams and also won a Vezina and Jennings Trophy. The Oilers were a powerhouse when Fuhr played from 1981 to 1991. He didn’t care if he won a game 1-0 or 10-9 as it was his job to simply make sure he won the contest by any means possible. Oilers’ fans were crushed when Fuhr was sent packing to Toronto in September of 1991 along with high-scoring winger Glenn Anderson and tough guy Craig Berube for Vincent Damphousse, Scott Thornton, Luke Richardson, and goaltender Peter Ing. Fuhr had lost just 117 games in 423 outings at the time while Anderson had 906 points in 845 games. Anderson is also a Hall of Famer, a four-time All-Star, and six-time Stanley Cup winner. Both Fuhr and Anderson were traded again, but their first deals definitely left fans scratching their heads.

8. Wendel Clark

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

Any Maple Leafs fan will tell you that rugged winger Wendel Clark was one of the most beloved players to ever wear the blue and white. Clark was the first-overall pick in 1985. He had a tremendous wrist shot, dropped the gloves with anybody, and hit anything that moved. However, his playing style was tough on a 5-foot-11-inch frame. Clark scored 34 goals in 66 games as a rookie and had over 30 goals in three of his first four seasons in Toronto, peaking at 46 in 64 games during the 1993-94 season. Clark was dealt in a blockbuster trade the next summer though as he went to the Quebec Nordiques with Landon Wilson, Sylvain Lefebvre, and a first-round draft round choice for Mats Sundin, Todd Warriner, Garth Butcher, and a first-rounder. Clark was traded three more times in his career and was reacquired by Toronto in March of 1996. He had two 30-goal seasons in three years before leaving for Tampa, Detroit, and Chicago, but being a Leaf at heart he returned to Toronto before retiring in 1999-2000. Fans were hurt at the time of the trade, but there’s no doubt they warmed up to that Mats Sundin guy.

7. Patrick Roy

Brad Rempel-USA TODAY Sports

Brad Rempel-USA TODAY Sports

Montreal found a gem in goaltender Patrick Roy by drafting him in the third round in 1984. The Hall of Famer retired in 2003 as an 11-time All-Star, four-time Stanley Cup winner, three-time Conn Smythe and Vezina Trophy winner, and a five-time Jennings Trophy recipient. He’d already won a pair of Stanley Cups in Montreal along with numerous trophies and had lost just 175 of his 551 regular-season games. However, he was traded to the Colorado Avalanche with Mike Keane for Martin Rucinsky, Andrei Kovalenko and fellow goalie Jocelyn Thibault on December 6th, 1995. Making the deal worse for Habs’ fans was the fact Keane was captain of the team. The trade came just a few days after Roy allowed nine goals on 26 shots in an 11-1 home loss to Detroit. Roy said coach Mario Tremblay left him in net to humiliate him before yanking him in the second period, before Roy told Habs’ owner Ronald Corey he was finished. The goalie was then suspended by the team and quickly traded.

6. Paul Coffey

Perry Nelson-USA TODAY Sports

Perry Nelson-USA TODAY Sports

Edmonton traded a lot of its stars of the 1980s, including Hall of Fame defenceman Paul Coffey. The blueliner was taken sixth overall in the 1980 draft and was seen to be the second coming of Bobby Orr as he was an offensive wizard. Coffey was a 14-time All-Star game player who won three Norris Trophies, and four Stanley Cups. He retired in 1998-99 with 1.531 points in 1.409 regular-season contests. Coffey had won three Cups with Edmonton by 1987 and racked up 669 points in just 532 games. However, he was traded away to Pittsburgh in November of 1987 with Wayne Van Dorp and Dave Hunter for Craig Simpson, Chris Joseph, Dave Hannan, and Moe Mantha. The Oilers’ fans were gob smacked to see the league’s top-scoring blue liner moved at the time. Coffey got used to living out of a suitcase though as he was traded six more times during his career before calling it quits.

5. Brian Spencer

via penguins-hockey-cards.com

The story of Brian ‘Spinner’ Spencer is one of the most tragic in league history. The left-winger from British Columbia was drafted 55th by Toronto in 1969. His hard-nosed play saw him make the Leafs a year later and he was scheduled to be interviewed on Hockey Night in Canada in December of 1970. Spencer’s father Roy held a party to see his son on TV, but was outraged when the local CBC channel broadcast the Vancouver Canucks game instead. Roy took a gun to the closest CBC affiliate and demanded they show the Leafs game. By the time he left the building, the RCMP had caught wind of the situation and Roy was killed in a shootout. Spencer found out about his father’s death after the game, but played the next night and had two assists and two fights, becoming an instant fan favourite.

Spencer had 30 points in 95 games with Toronto before the Islanders picked him up in the Expansion Draft of 1972. The 23-year-old alternate captain had 59 points in 132 outings with New York before the being traded to Buffalo in 1973. Spencer scored 114 points in 240 contests with Buffalo as a grinder and helped the team reach the Cup Final before being traded to Pittsburgh for Ron Schock in 1977. Spencer scored 223 points and 635 penalty minutes in 553 games before retiring from the sport in 1980. He became a drifter in Florida, was cleared of a murder charge in 1987, and was shot to death in June of 1988 at the age of 38. Spencer was a huge fan favourite everywhere he played and his life was detailed in a book and movie called Gross Misconduct..

4. Doug Gilmour

John E. Sokolowski-USA TODAY Sports

John E. Sokolowski-USA TODAY Sports

Yet again we have another player who was traded more than once and more than one set of fans were left mourning the deals. High-scoring and tough-checking centre Doug Gilmour carved out an excellent NHL career for himself with several different teams. The Hall of Famer wasn’t drafted by St. Louis until the 134th pick in 1982, but he was a two-time All-Star, a Stanley Cup winner, and recipient of the Frank Selke Trophy. And let’s not forget he scored 1,414 points in 1,474 games before retiring due to a knee injury in 2003. Gilmour was loved by fans everywhere he played due to the work ethic, leadership qualities, and scoring skills he displayed for such as small player. He spent five years in St. Louis before being dealt to Calgary in September of 1988 in a seven-player deal. Gilmour helped the flames win a Stanley Cup and was then part of a 10-man trade when he was sent to Toronto in January of 1992. Gilmour helped turn the Leafs around at that time and a third set of fans were heartbroken when he was traded to New Jersey in a five-player trade. He also played with Buffalo and Montreal before returning to Toronto and injuring his knee in his very first game back.

3. Phil Esposito

via bleacherreport.com

via bleacherreport.com

Centre Phil Esposito made his NHL debut in 1963-64 and scored 174 points in 235 games. Chicago fans didn’t really know what to make of him though since he was a relatively weak skater. Some were upset when he was traded to Boston in May of 1967 with Fred Stanfield and Ken Hodge for Jack Norris, Gilles Marotte, and Pit Martin, while others thought it was a good deal. However, just about every Bruins’ fan was crushed when Esposito was sent with Carol Vadnais to the New York Rangers in November of 1975 for Jean Ratelle, Brad Park, and Joe Zanussi in another blockbuster. The Bruins got a couple of Hall of Famers back in the deal in Ratelle and Park, but were giving up arguably the best scorer in hockey at the time as well as a fine defenceman in Vadnais. While in Boston, Esposito had won two Stanley Cups, earned eight straight All-Star nominations, five Art Ross Trophies including three in a row, and a pair of Hart Trophies. He also had 1,012 points in just 625 games.

2. Teemu Selanne

Kelvin Kuo-USA TODAY Sports

Kelvin Kuo-USA TODAY Sports

The Finnish Flash, Teemu Selanne took the NHL by storm as a rookie in 1992-93 after being drafted 10th overall by Winnipeg in 1988. Selanne shattered records by scoring 76 goals and 56 assists for 132 points. He proved it wasn’t a fluke as the Hall of Famer retired in 2014 with 684 goals and 773 assists for 1,457 points in 1,451 games. He won a Calder, Maurice Richard, and Masterton Trophy, was named to the All-Rookie team, 10 All-Star squads, and won a Stanley Cup. Selanne scored 306 of those points in just 231 games with the Jets before the team sent the fans berserk by trading him. Selanne had 72 points in 51 games in the 1995-96 campaign when he was sent to Anaheim with Marc Chouinard and a fourth-round draft choice for Oleg Tverdovsky, Chad Kilger, and a third-round draft pick. Anaheim fans felt the same way when Selanne was traded to San Jose for Steve Shields, Jeff Friesen, and a second rounder in March of 2001. Selanne would later return to Anaheim and win a Cup.

1. Wayne Gretzky

Perry Nelson-USA TODAY Sports

Perry Nelson-USA TODAY Sports

To many, centre Wayne Gretzky changed the face of the game and is the greatest player to lace up a pair of skates. He’s certainly the best-ever offensive player the game has seen. He broke into the NHL with Edmonton in 1979-80 as a 19-year-old after a 110-point season in the WHA. Gretzky spent nine seasons with the Oilers in the NHL and racked up numerous trophies, accolades, and milestones. These include four Stanley Cups between 1984 and 1988. Gretzky was the darling of Edmonton, the face of hockey around the world, and the most prolific scorer ever. However, he wasn’t above being traded. The hockey world was stunned on August 9th, 1988 when The Great One was dealt to the Los Angeles Kings along with Marty McSorley and Mike Krushelnyski for Jimmy Carson, Martin Gelinas, and the Kings’ first-round draft round choices in 1989, 1991, and 1993 as well as a ton of cash. Gretzky would be traded once again in his career from LA to St. Louis in 1996, but it was nothing compared to the heartbreak of Oilers’ fans the first time he was dealt.

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