Calgary trades Brett Hull: In March 1988, the Flames traded Hull and Steve Bozek to the St. Louis Blues. In exchange, they received defenceman Rob Ramage and goalie Rick Wamsley. Ramage did help the Flames win their only Stanley Cup in 1989 with 12 points in 20 playoff games but Wamsley played a little over three seasons as a backup netminder. Hull, however, went on to score 527 goals for the Blues and write his name in the NHL record books beside that of his father, Bobby Hull. Brett also won the Hart Trophy in 1991 as the NHL's most valuable player. The Flames couldn't plead ignorance — Hull had already scored 50 points in just 52 games for them in the 1987-88 season. The edge on this one clearly went to St. Louis.
Edmonton trades Wayne Gretzky: Ever eager to win the battle of Alberta, Edmonton gets two deals on the list. While you can argue there was no attempt to come out a winner in 1988 — it appeared to be all about the money for a cash-strapped owner — the deal itself set the stage for Edmonton's decline as a hockey power. The Oilers traded Gretzky, Mike Krushelnyski and Marty McSorley (they were part of the deal at Gretzky's request) to the Los Angeles Kings. Edmonton got that $15 million in cash owner Peter Pocklington needed plus Jimmy Carson, Martin Gelinas and three first-round draft choices. The Kings and NHL benefited from the higher profile Gretzky created for the sport south of the border but Pocklington was burned in effigy by angry fans.
Edmonton trades Mark Messier: The coup de grace for a dynasty that won five Stanley Cups in seven years was delivered after the Oilers won what would be their last Stanley Cup in 1990. They shipped Mark Messier to the New York Rangers the following year. To be fair, Messier was no longer happy with the Oilers, who even threw in future considerations to sweeten the deal. In return, Edmonton received forwards Bernie Nicholls, Steven Rice and Louie DeBrusk. Nicholls was the best of the bunch with 49 and 40 points, respectively, over the next two seasons before he moved to New Jersey. Messier, however, immediately delivered 107 points for New York and went on to lead the Rangers to a Stanley Cup win in 1994.
Canucks trade Cam Neely: OK, he was just 20 at the time and had only scored 51 goals in three seasons. But Vancouver fans won't forget the Neely trade in the 1985-86 campaign, when a future Hall of Famer was dealt to the Bruins. Neely became one of the grittiest and most productive players in the Boston lineup. For example, injuries kept him out of all but 49 games in 1993-94, but Neely still managed to score 50 goals. Vancouver got centre Barry Pederson in the deal but also gave up a first-round pick that Boston used to select defenceman Glen Wesley. As a final insult, in 2011 — with Neely as president of the Bruins — Boston defeated the Canucks to win the Stanley Cup.
Florida trades Roberto Luongo: The Panthers' 2006 deal with the Vancouver Canucks included Luongo, Czech defenceman Lukas Krajicek and a sixth-round pick (Russian forward Sergei Shirokov). Neither Krajicek nor Shirokov had a very long NHL career. Vancouver gave up goalie Alex Auld, defenceman Bryan Allen and forward Todd Bertuzzi. Only Allen stuck with Florida for more than a season. Bertuzzi played just seven games. Luongo, who had set several franchise records over five seasons with Florida, continued his stellar play for several years with the Canucks. Former Panthers coach and general manager Jacques Martin later said the trade was the worst in NHL history.