The Five Worst Trades in NHL History

Esposito, Thornton Involved in Hockey’s Biggest Dud Deals

There are bad trades, and then there are these five, among the worst in the history of the NHL.

Sure, there have been lots of lopsided deals in the history of the NHL. But it is hard to imagine that there are trades worst than the following five. So here, in no particular order, are the five worst trades in NHL history:

Chicago Trades Phil Esposito, Ken Hodge and Fred Stansfield to Boston for Pit Martin, Gilles Marotte and Jack Norris

Many hockey fans were surprised when Bobby Hull’s centre was shipped off to Boston in 1967, but you could imagine their reaction over the next ten seasons, when Esposito would mature into one of the league’s top scorers. Esposito became the first player in league history to top the 100-point plateau in a season, and then had five more 100-point seasons in a row during the early 1970’s. Esposito became a two-time Hart Trophy winner for league MVP, an icon for the sport, and a future Hall of Famer in 1984. To make matters worse for Chicago fans, Hodge also had two 40+-goal seasons and a 50-goal campaign in 1973-74. Even Stansfield, considered a spare part in this blockbuster deal, had six straight 20+-goal campaigns for Boston from 1967 through 1973.

As for Martin, he went on to be an All-Star and captain for the Blackhawks. Martin even hit the 30-goal plateau three times in Chicago. Marotte was an All-Star himself in 1973 and bounced around for several teams in the league before defecting to the WHA in 1978. Norris played part of eight seasons in the NHL and the WHA before retiring in 1976. But none of their contributions to the Blackhawks could even come close to those of what Esposito, Hodge and Stansfield contributed to the 1970’s Bruins juggernaut.

Boston Bruins Trade Joe Thornton to San Jose for Marco Sturm, Brad Stuart and Wayne Primeau

At the time of his departure to San Jose in 2005, Thornton was heavily criticized by Bruins fans and Boston media outlets for his lack of offensive production in the playoffs and his leadership abilities. Less than one year into a three-year, $20 million deal he had just signed with the Bruins, the club dealt him to the Sharks for a trio of players, all of whom while solid players, would never put up the numbers Thornton had or continues to put up to this day. In San Jose, Thornton was the league’s leading scorer in 2006, scoring 92 points with the Sharks that season in just 58 games, and as a Shark, he has had four 85+point seasons. Meanwhile, Stuart eventually went to Detroit and Primeau to Toronto. Sturm is the only one of the three to have remained with Boston and, while there, he has had three-straight 20+ goal seasons for the club.

Vancouver Sends Alek Stojanov to Pittsburgh for Markus Naslund

At the time of this deal, hard to believe as it may seem, Stojanov may have been the bigger of the two names. A former 1st round pick (7th overall) by the Canucks in 1991, he never quite found a place in their organization. Stojanov was shipped to Vancouver for Naslund, who at the time amassed 25 goals in parts of three seasons in Pittsburgh. Subsequently, Naslund would explode as one of the league’s top offensive threats of the last decade, with three consecutive 40+-goal seasons in Vancouver, five All-Star appearances and a Hart Trophy nomination in 2003. Stojanov fizzled out of the NHL by 1997, and played in the minors until his retirement in 2002.

N.Y. Islanders Trade Zdeno Chara, Bill Muckalt, and Their 2001 1st Round Pick to Ottawa for Alexei Yashin

For sheer volume, this arguably is one of the worse trades then-Islanders’ G.M. Mike Milbury ever made, and he made quite a few doozies during his reign on the Island. The club moved a future four-time All-Star and 2009 Norris Trophy winner in Chara, as well as the pick that would eventually become Jason Spezza and Muckalt, to Ottawa, for Yashin. He was then immediately signed by Milbury to a 10-year, $87.5 million deal, and in five seasons with the club, saw his numbers steadily decline after an initial 75-point season in 2001-02. Seemingly untradable, Yashin had his contract brought out by the club in 2007, and he has spent the last three seasons playing in his native Russia.

Vancouver Trades Cam Neely and Their 1987 1st Round Pick to Boston for Barry Pederson

One of the all-time great blunders in NHL trading history, Neely was buried in the Vancouver organization as a middling forward and was swapped straight up for Pedersen, a solid defensive-first winger who amassed a decent NHL career, but no where near what Neely accomplished. Neely went on to become beloved in Boston, with three 50+ goal seasons, in a career that culminated in being inducted into the Hockey Hall of Fame in 2005. To make matters worse, that 1st round pick involved in this deal, the third pick overall in 1987, was used by Boston to select defenseman Glen Wesley, who played seven seasons on the blueline with the club.

Michael Spagnuolo, Taken By: Patricia Piersimoni

Michael Spagnuolo - Hello - my name is Michael Spagnuolo. I have worked for several years behind the scenes with two NHL teams, and I have also played ice ...

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