We all make mistakes, but few of us will ever do so under as intense scrutiny as that faced by an NHL general manager. Their jobs are far from enviable, filled with immense pressure, expectations and second-guessing. Even those with proven success pulling a floundering team back into the playoffs or leading a good team all the way to Stanley Cup glory are not safe from a public indictment and calls for their job if they make an error in their player management. Sometimes mistakes are apparent immediately, as when a GM trades his star player for low value due to personal, financial or on-ice reasons. Others, however, are not apparent until years later, as a draft pick or young prospect is traded away for a safer or older player, and the young player emerges as a superstar on their new team.
In some cases, these moves are beneficial for both teams. In March 1988, the Flames sent Brett Hull to St. Louis for Rick Wamsley and Rob Ramage, neither of whom would ever approach Hull's Hall of Fame production. Wamsley and Ramage, however, were both members of the Flames' Stanley Cup winning team in 1989. While there is no guarantee that they were the difference, or that the team would have failed to win a Cup with Hull instead of them, the Flames still won the Stanley Cup, while the Blues did not with Hull. A team's success, therefore, must be considered when evaluating trades as well.
The following fifteen trades, however, were unmitigated disasters for one team and steals for another. One's perspective on them may depend on which team they prefer, but no one can deny that these trades made significant differences to the teams involved and that they were far from even transactions.
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15 Patrick Roy to Colorado from Montreal
Four days after being forced to stay on the ice for nine goals against in an 11-1 home loss to Detroit, Roy's wish to never play for the Canadiens again was granted. The three players Montreal received back (Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault) all served as slightly below average contributors for Montreal, and Roy forced Montreal's hand, so the trade does not stand as high as it may have on this list. Trading away arguably the best goaltender in NHL history is a poor decision, so regardless of Roy's forcing their hand, the trade remains a mistake for the Canadiens.
14 Zdeno Chara and 2nd Overall Pick (Jason Spezza) to Ottawa from the New York Islanders for Alexei Yashin
Yashin's contract holdout in 1999-2000 should have served as a red flag for the Islanders, but they still sent a young Chara, the second overall pick, and winger Bill Muckalt to acquire his services in 2001. The Islanders bought out Yashin's 10 year, $87.5 million contract in 2007 and still pay him today. Chara, meanwhile, matured into one of hockey's best defenseman, and the second overall pick was used to select long-time first line center Jason Spezza.
13 First Round Pick (Scott Niedermayer) to New Jersey from Toronto
In 1989, Leafs GM sent their first round pick to acquire defenseman Tom Kurvers, coming off a career-best 66 point season. Kurvers also scored 52 points in his first season for the Leafs, but his career is best remembered for being traded for the pick used to take Scott Niedermayer, one of the best defensemen in NHL history. The Leafs had no idea they were losing Niedermayer initially, but the trade stands in retrospect as an enormous mistake for the Leafs.
12 Dominik Hasek to Buffalo from Chicago
In 1992, Chicago already had a young Ed Belfour, as well as promising 1987 first round pick Jimmy Waite in net, while Hasek had only played 25 games for the Blackhawks, and therefore seemed expendable. The Blackhawks, however, received only blueliner Stephane Beauregarde and a fourth round pick in 1993 (Eric Daze) for Hasek, and Waite spent much of his later career in Europe as Hasek became a six-time Vezina and two-time Hart winner. Advantage: Buffalo.
11 Markus Naslund to Vancouver from Pittsburgh
Pittsburgh, in 1996, dealt Naslund, who already had 52 points in 66 games, for defenseman Alek Stojanov, who had scored one point in 62 career games. Stojanov only scored six more points in 45 career games before dropping down to the IHL two years later. Naslund, on the other hand, became the Canucks' captain and leading scorer for several seasons. Some trades have complex legacies, but this one is unmistakably and woefully lopsided in the Canucks' favour.
10 First Round Pick (Guy Lafleur) to Montreal from California Golden Seals
First, Montreal GM Sam Pollock acquired the California Golden Seals' first round pick in 1971 and Francois Lacombe for his first round pick in 1970 (Chris Oddleifson, who never played for California but became Vancouver's captain in the late 70s) and winger Ernie Hicke. He then dealt centre Ralph Backstrom to LA in early 1971 to help them finish above California and guarantee the Canadiens could use the acquired pick to select Lafleur first in the draft. Brilliant maneuvering by Pollock.
9 Doug Gilmour to Toronto from Calgary
Gilmour was sent to Toronto, along solid defenseman Jamie Macoun and three other players, to Calgary for a package of five players, most notably former 50 goal scorer Gary Leeman. Only one of the five traded to Calgary would stay with the Flames for more than two years, and none of them made an impact. Gilmour, in contrast, recorded seasons of 127 and 111 points in 1992/93 and 1993/94, becoming one of the most beloved Leafs players of the modern era.
8 Rick Middleton to Bruins
After unwisely sending Phil Esposito to New York for Jean Ratelle and Brad Park in 1975, the Rangers compounded their mistake in 1976. New York acquired Ken Hodge, Esposito's former linemate in Boston, and gave up Rick Middleton, a talented but immature forward, to get him. Hodge only played one and a half seasons before finishing his career in the minors, while Middleton matured in Boston, scoring 40 or more goals five times and over 400 career goals as a Bruin.
7 Cam Neely and a First Round Pick (Glen Wesley) to Boston from Vancouver
Barry Pedersen was set for stardom, having recorded two seasons each of at least 40 goals and 100 points by age 25, but had his career derailed by injuries. The Bruins were wise enough to trade him just before he went into severe decline. In exchange, they got a first round pick, which they used to draft talented defenseman Glen Wesley and Cam Neely. Despite his own injury problems, Neely recorded three seasons of 50 or more goals, and retired with nearly a point per game average.
6 Adam Oates to St. Louis from Detroit
Oates spent less than three years in St. Louis, but recorded 228 assists in just 195 games as Brett Hull's linemate there, helping Hull to record seasons of 72, 86 and 70 goals respectively. Without Oates, Hull only broke the 50 goal plateau two other times in his career. In return for Oates, Detroit got only Tony McKegney, who recorded a mere three points as a Red Wing before moving on to Quebec, and Bernie Federko, who retired after one season in Detroit.
5 Mark Messier to the New York Rangers from Edmonton
After winning five Stanley Cups with the Oilers and serving as team captain, Messier was ignominiously shipped to the Rangers on October 4, 1991, along with Jeff Beukeboom, for Bernie Nicholls and prospects Steven Rice and Louie DeBrusk. None of the three became impact players in Edmonton, while Messier led the Rangers to win the Stanley Cup in 1994, their first since 1940, and further established himself as one of the NHL's greatest captains, point producers and clutch performers.
4 Tuukka Rask to Boston from Toronto
Since joining the Bruins in 2006, Rask has become the team's starting goaltender, won a Vezina and has finished with a GAA of 2.05 or lower in four of the past five seasons. What did Toronto get for him? Andrew Raycroft, who sadly peaked as a rookie. He served as starter in Toronto for one season, recording an underwhelming 2.99 GAA and .894 save percentage, before spending another year as backup and then moving to Colorado. Justin Pogge, Toronto's heir apparent and the reason for their decision to trade Rask, never cracked an NHL roster and now plays in Sweden.
3 Marcel Dionne to Los Angeles from Detroit
When Detroit traded Dionne in 1975, they knew they were losing an incredibly talented player. After being drafted second overall, Dionne had put up seasons of 77, 90, 78 and 121 points to start his NHL career. Upset with Detroit's inability to make the playoffs, however, Dionne was accommodated and moved to Los Angeles for Dan Maloney, Terry Harper, a second round pick and cash. While Dionne never won a Stanley Cup, he did put up six fifty goal seasons in seven years, and finished with 731 goals and 1,771 points in his career, good for fourth and fifth all time respectively.
2 Phil Esposito, Ken Hodge and Fred Stanfield to Boston from Chicago
In 1967, Chicago received Pit Martin, who had a consistently solid career, as well as Gille Marotte and Jack Norris, but they lost three players who were each better than any of the ones they got back. They lost Fred Stanfield, who provided consistent secondary scoring, recording between 54 and 79 points in each of his six seasons in Boston. Ken Hodge partnered with Esposito to score at least 40 goals three times, including one fifty goal season, and two 100 point seasons. Most importantly, they lost Phil Esposito, who became one of hockey's most unstoppable offensive forces, recording at least 55 goals five times, including one 76 goal season, and over 125 points six times. Esposito also won five Art Ross trophies and two Hart Trophies.
1 Wayne Gretzky to Los Angeles from Edmonton
"The Trade," which sent Gretzky, Marty McSorely and Mike Krushelynski to Los Angeles for Jimmy Carson, Martin Gelinas, three first round picks and $15 million dollars, is even more painful because of the motivation behind it. Peter Pocklington, the Oilers owner, was desperate for money and demanded the $15 million as the key part of the trade. Gretzky's success in Los Angeles sparked a wave of Southern expansion in the US, and while Gretzky never won another cup and the Oilers went onto win another Stanley Cup two years later in 1990, the team was never quite the same without him as Gretzky continued to dominate hockey.
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