The 10 worst trades in NHL history. (Featuring the Maple Leafs)

When it comes to trades in the NHL, hindsight is always 20/20. What seems like a fair trade at the time can sometimes end up crippling a team for years to come.While many factors go into making trades, the goal is always t improve your hockey club.On these occasions, one team got great return, while the other was left holding the bag. Sometimes things just do not work out the way you expect them to. These are ten NHL trades that were miserable failures. 10. The Toronto Maple Leafs trade Russ Courtnall to the Montreal Canadiens for John Kordic and a sixth-round draft pick on November 7, 1988. For former Leafs GM Gord Stellick, this was on trade that contributed to his short lived career with the blue and white. Kordic was never a prolific goal scorer. He finished his 9 year NHL career with just 35 points. His ability to be physical and engage in fights was his true claim to fame. Kordic tragically took his own life four years later. Courtnall, on the other hand was an offensive wiz. Courtnall totaled 744 points in his 19-year career and was a very important piece of the Canadiens organization. He could be counted on as a goal scorer and good two-way player. The Leafs were unfortunate losers in this trade. 9. The Edmonton Oilers trade Miroslav Satan to the Buffalo Sabres for Barrie Moore and Craig Millar on March 18, 1997 Former Oilers GM Glen Sather was not known for making bad trades, but this one definitely turned out bad for the Oil. In an attempt to shed salary the Oilers traded Satan for Barrie Moore and Craig Miller. Moore only played in 39 pro games and Miller played 114 over a five year career. Satan on the other hand, played in 1050 NHL games with Edmonton, Buffalo, New York Islanders, Pittsburgh, and Boston. He played in the Winter Olympics four times, twice in the World Cup of Hockey, and multiple times at the World Hockey Championships. He recorded 363 goals and 372 assists for 735 points in his career. He was exciting to watch and a key contibuter to all those teams. Needless to say, he outperformed Moore and Miller combined. 8. Calgary Flames trade Brett Hull and Steve Bozek to the St. Louis Blues for Rob Ramage and Rick Wamsley on March 7, 1988 Drafted 117th by Calgary in 1984, the "Golden Brett" would be destined for a Hall Of Fame career. Son of Bobby Hull and nephew to Dennis Hull, hockey was in his blood. Over the course of his career, Hull won two Stanley Cups, had eight All-Star Game appearances, plus a Hart and Lady Byng Trophies. In 1269 games, Hull compiled 741 goals and 640 assists for 1391 points, making him one of the most prolific scorers in recent memory. While Ramage won two Stanley Cups and Bozek won one, they were never close to matching Hull's contributions. Ramage was the better of the two, playing in four All-Star games over 15 seasons. Bozek's best season was his first, but he did play for 10 additional seasons. Neither player was even close to the level that Hull was. Calgary would love to turn back the clock on this one. 7. The New York Islanders trade Roberto Luongo and Olli Jokinen to the Florida Panthers for Oleg Kvasha and Mark Parrish on June 24, 2000 Roberto Luongo is widely considered one of the most solid goaltenders in the NHL. Although he has recieved some criticism regarding his play in the playoffs, he has consistently remained a number one goalie in this league and has achieved a lot of success. Olli Jokinen is still playing at a high level to this day. The Islanders got the short end of the stick as Parrish’s career lasted only 11 seasons scoring only 387 points. Kvasha never developed into anything other than a role player. Mike Milbury's disregard for Luongo and Jokinen left his team in the hole for years to come. 6. The Pittsburgh Penguins trade Markus Naslund to the Vancouver Canucks for Alek Stojanov on March 20, 1996 Alek Stojanov was a very highly touted prospect at the time he was drafted. Stojanov was drafted by the Vancouver Canucks in the 1991 NHL Draft 7th overall. Unfortunately for the Penguins, his NHL career was short lived as he only managed to play 107 games total. Markus Naslund on the other hand was a force to be reckoned with. He played 1,117 career games, acquiring 867 points during stops with Pittsburgh and Vancouver before ending his career with the New York Rangers. He also made numerous international appearances. Naslund ended up becoming the Canucks all-time leading scorer, making this trade extremely lopsided in hindsight. 5. The New York Islanders trade Zdeno Chara, Bill Muckault and 2001 1st round pick (Jason Spezza) to Ottawa Senators for Alexei Yashin on June 23, 2001 Alexei Yashin seemed like the real deal. He was drafted 2nd Overall by the Sens' in 1992 and led the team to the playoffs and their first series win over the New Jersey Devils. After fights with management over contract negotiations, he was dealt to the Islanders. During five seasons in Long Island, his production declined rapidly and he never bounced back. He is considered a bust by most hockey fans. Ottawa won the lottery in this trade. Zdeno Chara would develop into one of the most dominant blueliners in the NHL. He is still wreaking havoc to this day with the Boston Bruins. The 1st round pick they acquired turned into Jason Spezza, who led the team to the Finals in 2007, before losing against Anaheim. He was a mainstay for the Sens for a long time and a great contributor during that time. He continues to perform at a high level as a member of the Dallas Stars. This deal effectively ended Islanders GM Mike Milbury’s career. 4. The Toronto Maple Leafs trades the rights to Tukka Rask to Boston Bruins for Andrew Raycroft on June 24, 2006 Former Leafs GM John Ferguson Jr. must be kicking himself for making this deal. Maple Leaf Sports and Entertainment (MLSE) forced Ferguson's hand with a “make the playoffs or else” attitude. Andrew Raycroft won the Calder Trophy after the 2003-2004 season. Toronto thought Raycroft could be the goaltender of the future. Unfortunately for them, Raycroft played only two seasons in Toronto and over 91 career games he compiled a very average record of 39-34-14. On April 9, 2014 Raycroft retired from professional hockey. Rask was drafted by Toronto in 2005 and after the trade he developed into one of the NHL's premier goaltenders. Rask won a Stanley Cup ring with Boston in the spring of 2011 over the Vancouver Canucks. He has helped Boston become a consistent contender year after year. This trade is a memory that Leaf Nation would like to forget. 3. The Montreal Canadiens trade Patrick Roy and Mike Keane to Colorado Avalanche for Jocelyn Thibault, Martin Rucinsky and Andre Kovalenko on December 6, 1995 On December 2, 1995, the Detroit Red Wings played against the Montreal Canadiens and massacred them 11-1. Canadiens coach Mario Tremblay left Roy out to dry due to conflict between the two. After he was finally pulled, Roy told Tremblay and team president Ronald Corey, “It’s my last game in Montreal!” Four days later he was dealt to Colorado. Roy was considered one of the best goalies to ever play. Needless to say, the Habs lost on this deal. 2. The Toronto Maple Leafs trades their first round pick (3rd overall – Scott Niedermayer) to the New Jersey Devils for Tom Kurvers on October 16, 1989 Many Leafs fans consider this to be the worst trade in team history. Tom Kurvers was not a bad player, but he was far from a superstar. Kurvers’ best season came in the 1988-89 season, where he accumulated 66 points over 74 games. It was these numbers that prompted the Leafs t trade their pick for him. That pick turned out to be Scott Neidermayer. Neidermayer won a Norris Trophy, a Conne-Smythe Trophy, four Stanley Cups, as well as two Gold medals at the Winter Olympics. He was also inducted into the Hockey Hall of Fame. He was a staple on the Devils blueline his entire career and is considered one of the best players in franchise history. Toronto really screwed the pooch on this one. 1. The Edmonton Oilers trade Wayne Gretzky, Mike Krushelynski and Marty McSorley to the Los Angeles Kings for Jimmy Corson, Martin Gelinas, 3 1st round picks as well as $15M on August 9, 1988 Oilers owner Peter Pocklington was struggling financially at the time and was in need of capital for the team. Only two hours after winning their fourth Stanley Cup in 1988, Gretzky learned the team had planned on trading him. Worst of all the team informed him he had been traded during his honeymoon. Gretzky did not want to leave Edmonton whatsoever. The choice was not his to make. This deal helped opened the doors for hockey in the southern U.S, and Kings owner Bruce McNall could not have asked for a better player to lead his team. Five years later, the Kings played in the Finals only to lose to Montreal. The Oilers did win one cup after Gretzky's departure, but this trade ultimately marked the end of an era in Edmonton. The team has never reached the high of that decade and fans have been looking for something to look forward to ever since. Did we leave any out?