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Hockey's 5 worst GM moments

1. Pollock schools Finley and Regan

Montreal Canadiens general manager Sam Pollock really wanted Guy Lafleur, but he wouldn't have got him without exploiting the idiocy of others.

First Pollock had to convince a bad team to give up their 1971 first-round draft pick, which he finally managed when he persuaded California Golden Seals owner Charlie Finley to part with his first-round pick and depth defender Francois Lacomb on May 22, 1970. In exchange the Canadiens sent the Golden Seals their first-round pick and promising young forward Ernie "Bubbles" Hicke, who had a decent enough career.

Everything was going according to plan for the Canadiens, until the Golden Seals were just slightly outpacing the woeful Los Angeles Kings. It looked like, maybe, the Canadiens would have to settle for the second overall pick instead!

Pollock had no plans of selecting Marcel Dionne though. Instead he convinced Kings general manager Larry Regan to trade him spare parts for aging center Ralph Backstrom in midseason. Backstrom managed to accumulate 27 points in Los Angeles' final 33 games, leading them out of the cellar and allowing the Canadiens to select Lafleur with the first overall pick.

2. The Francis Trade

Lopsided trades happen in hockey, but the Ron Francis trade was so bad that it doomed NHL hockey in Hartford.

On March 4, 1991 Hartford Whalers general manager Eddie Johnson dealt captain Ron Francis, defenseman Ulf Samuelsson, and Grant Jennings to the Pittsburgh Penguins in exchange for Jeff Parker, John Cullen, and Zarley Zalapski. 

When you trade a guy who goes on to score 613 points and win two Stanley Cup trophies with his new team, and the most notable player you got in return was Zarley Zalaspski, well, that's just awful.

3. The Flyers play Kingmaker

In June of 2011 the Philadelphia Flyers, just 12 months removed from an appearance in the Stanley Cup Final, traded Jeff Carter and Mike Richards to the Columbus Blue Jackets and the Los Angeles Kings respectively. 

The trades themselves weren't so bad, in fact they look pretty decent in retrospect as the Flyers netted  a bounty of useful pieces including Wayne Simmonds, Brayden Schenn, Jakub Voracek, and Sean Couturier. 

In a vacuum, the deals worked out. 

NHL transactions don't occur in a vacuum though, and the critical context here is this: Flyers general manager Paul Holmgren made these trades to free up salary cap space that he then used to sign goaltnder Ilya Bryzgalov. The deal turned out to be one of the most misguided contracts of the salary cap era. 

Carter and Richards, who were later reunited in Los Angeles after Carter pouted until the Blue Jackets agreed to deal him, would go on to win two Stanley Cups within three years. Meanwhile the Flyers bought out Bryzgalov's oversized deal in 2013. 

4. Mike Gillis misjudges the goalie market

It's not a coincidence that the two examples from the salary cap era included bloated goalie contracts.

While the goalie market has flummoxed many a contemporary NHL executive, no one mismanaged and misjudged the market worse than former Vancouver Canucks general manager Mike Gillis.

In 2012, Gillis went to the entry-draft and it was widely assumed that he'd be moving a goaltender - either highly paid veteran star Roberto Luongo, or promising blue-chip backup Cory Schneider. 

Blocked by Luongo, who was unwilling to waive his no-trade clause at that point, Gillis elected to hang on to both goaltenders.

Then the lockout happened, and the salary cap recapture clause was introduced. Luongo's contract was already going to be difficult to move, but the salary cap recapture clause made the Luongo contract toxic. 

In 2013, Gillis went to the entry-draft and it was widely assumed that he'd be desperate to find a way to move Luongo. Instead he traded Cory Schneider for the ninth overall pick and selected Bo Horvat. 

Luongo put on a brave face and tried to make it work in Vancouver during the 2013-14 season, but ultimately lost his starters job (again) to Eddie Lack. The final nail was when the Canucks elected to start Lack at the 2014 Heritage Classic.

Finally, Luongo's agent Pat Brisson managed to orchestrate a trade that got Luongo out of Vancouver and to his preferred destination. In exchange the Canucks received Jakob Markstrom, Shawn Matthias, and $800k worth of dead salary cap space through the 2021-22 season. 

5. Naslund for Stojanov 

The Canucks and the Penguins had a couple of young players, Alex Stojanov and Markus Naslund, both of whom weren't really working out and required a change of scenery.

On March 20, 1996 the two clubs swapped underachieving forwards - with Stojanov going to Pittsburgh, and Naslund joining the Canucks.

The deal remains one of the most lopsided in NHL history. Naslund would go on to record over 750 points with Vancouver over the course of 12 mostly successful season with the club. Stojanov meanwhile would appear in just 45 games with the Penguins, totalling just six points in those games.

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