"Once you’re a winner, you keep improving on perfection. You keep making trades and changes that will strengthen their team, even if they aren’t popular at the time. You go about your business."
Those are the words of the legendary Sam Pollock, arguably the greatest general manager in the history of the NHL. He's the man who brought Ken Dryden, Guy Lafleur, Larry Robinson, and Bob Gainey to Montreal, among many others. He built a Canadiens dynasty that won the Stanley Cup nine times during his 14-year tenure as GM. He's also the same man who let Hall of Fame goaltender Tony Eposito go in an intra-league draft, traded Vezina Trophy winner Rogie Vachon for practically nothing, and drafted Mark Napier over Mike Bossy.
Even the best in the business make mistakes sometimes. It's the price you pay for trying to build a team that can consistently win championships. Often you have to take big risks to make your team better even, as Pollock said, if it isn't the popular decision at the time. The difference between a bad manager, a good manager, and a great manager is knowing which risks are worth taking and keeping your failures to a minimum. But sometimes even the most calculated of risks can blow up in your face.
Every NHL team has, at one point or another in their history, made a trade that left fans shaking their heads. The great teams all found ways to recover from those trades and turn lemons into lemonade. Others have tried to fix their own blunders, only to make matters worse. Some of these trades have been forced by financial or personal decisions. Others are just completely baffling and leave you wondering how the person in charge ever got hired in the first place. Here's a look at every NHL team's worst trade. Note: the trades also take into account the franchises' entire histories, meaning some old Jets, Nordiques and Hartford Whalers trades will come up.
30 Anaheim Ducks
- Teemu Selanne for Jeff Friesen, Steve Shields and 2nd Rounder
29 Arizona Coyotes (Winnipeg Jets)
- Teemu Selanne, Marc Chouinard and 4th Rounder for Chad Kilger, Oleg Tverdovsky and 3rd Rounder
Of course, the Ducks aren't the only team to regret trading away the Finnish Flash. Selanne scored a rookie record 76 goals and 132 points for the original Winnipeg Jets in the 1992-93 season. However, 51 games and 71 points into his fourth NHL season - the Jets final season before the move to Phoenix - Selanne, Marc Chouinard, and a fourth round draft pick were traded to the Mighty Ducks for Chad Kilger, Oleg Tverdovsky and a third round draft pick.
Tverdosky got his tenure in Phoenix off to a nice start, posting a career high 55 points in his first season, but he was never able to establish himself as a top defenseman and was traded back to Anaheim after three season with the Coyotes. Kilger, meanwhile, was never able to justify his selection as the 4th overall pick in the 1995 NHL draft and spent most of his career as a third or fourth line winger. As for Teemu, he finished his career as the Ducks' all time leader in games played, goals, and points.
28 Boston Bruins
- Tyler Seguin, Rich Peverley and Ryan Button for Loui Eriksson, Reilly Smith, Matt Fraser and Joe Morrow
Following the 2013 Stanley Cup Playoffs, the Bruins were upset with 21-year-old Tyler Seguin for behaving like a 21-year-old and shipped the former 2nd overall pick to the Dallas Stars along with Rich Peverley and Ryan Button for Loui Eriksson, Reilly Smith, Matt Fraser and prospect Joe Morrow. Fraser and Smith are no longer with the Bruins and Morrow has yet to establish himself as a regular NHL defenseman.
27 Buffalo Sabres
- Dave Andreychuk, Daren Puppa and 1st Rounder for Grant Fuhr and 5th Rounder
Dave Andreychuk scored a career high 41 goals and 91 points for the Sabres in 1991-92 and had 29 goals and 61 points in 52 games midway through the 1992-93 season when he was traded, along with Daren Puppa and a first round draft pick, to the Toronto Maple Leafs for a 30-year-old Grant Fuhr and a fifth round pick. Andreychuk scored 25 goals and 38 points in 31 games following the trade and scored 12 goals and 19 points in 21 playoff games in the Maple Leafs run to the 1993 Conference finals. He followed that up with 53 goals and 99 points in 1993-94.
26 Calgary Flames
- Doug Gilmour, Ric Nattress, Kent Manderville, Jamie Macoun andRick Wamsley for Gary Leeman, Craig Berube, Alexander Godnyukk, Michael Petit and Jeff Reese
On January 2, 1992 Maple Leafs general manager Cliff Fletcher swung a massive 10 player deal with his former team, sending Gary Leeman, Craig Berube, Alexander Godynyuk, Michel Petit, and goaltender Jeff Reese to Calgary for Doug Gilmour, Ric Nattress, Kent Manderville, Jamie Macoun and goaltender Rick Wamsley. The deal paid immediate dividends for Toronto. In Gilmour's first full season in Toronto he picked up a franchise record 95 assists and 127 points while taking home the Selke Trophy and was the runner up for the Hart Trophy.
25 Carolina Hurricanes (Hartford Whalers)
- Ron Francis, Ulf Samuelsson and Grant Jennings for Jeff Parker, Zarley Zalapski and John Cullen
Current Hurricanes general manager Ron Francis was part of the franchise's worst trade when the Hartford Whalers traded him, Ulf Samuelsson and Grant Jennings at the 1991 trade deadline to the Pittsburgh Penguins for Jeff Parker, Zarley Zalapski, and John Cullen. Francis was the team's number one centre and held many of the franchise's records, but had already been stripped of his captaincy and was in the final year of his contract when the trade took place.
24 Chicago Blackhawks
- Phil Esposito, Ken Hodge and Fred Stanfield for Pit Martin Jack Norris and Gilles Marotte
During a 1967 Blackhawks team party, a drunken Phil Esposito said to Chicago general manager Tommy Ivan and coach Billy Reay, “We’ve got a great team here, you could almost have a dynasty, but you two are gonna screw it up.” He was right. That offseason the Blackhawks traded Esposito, Ken Hodge, and Fred Stanfield to the Boston Bruins for Pit Martin, Jack Norris, and Gilles Marotte. Of the three players Chicago got in the deal, only Martin made any real contributions, reaching the 30 goal mark three times and the 70 point mark four times, including a career high 90 points in 1972-73. However, those numbers pale in comparison to what they gave up.
23 Colorado Avalanche (Quebec Nordiques)
- Mats Sundin, Garth Butcher, Todd Warriner and 1st Rounder for Wendel Clark, Sylvain Lefebvre, Landon Wilson and 1st Rounder
The Quebec Nordiques had the first overall pick in three straight drafts from 1989-91, but by the time the team won its first Stanley Cup in Colorado, all three of those players had been traded away. While it's hard to argue with the results, the return for 1989's pick, Mats Sundin proved to be underwhelming. At the 1994 Draft, the Nordiques dealt Sundin, Garth Butcher, Todd Warriner, and a first round pick to the Maple Leafs for Wendel Clark, Sylvain Lefebvre, Landon Wilson, and a first round pick.
22 Columbus Blue Jackets
- Jakub Voracek, 1st Rounder, 3rd Rounder for Jeff Carter
Rumors were running rampant leading up to the 2011 NHL Draft that the Philadelphia Flyers were shopping stars forwards Mike Richards and Jeff Carter. After trading Richards to the Los Angeles Kings, they reached a deal to send Carter to the Blue Jackets for Jakub Voracek, the eighth overall pick, which the Flyers used to draft Sean Couturier, and a third round pick.
21 Dallas Stars
- James Neal and Matt Niskanesn for Alex Goligoski
20 Detroit Red Wings
- Marcel Dionne and Bart Crashley for Dan Maloney, Terry Harper and 2nd Rounder
19 Edmonton Oilers
- Wayne Gretzky, Marty McSorley and Mike Krushelnyski for Jimmy Carson, Martin Gelinas, three 1st Rounders and $15 million
In the summer of 1988, following the Oilers' fourth Stanley Cup victory in five years, financial trouble prompted Oilers owner Peter Pocklington to agree to a trade with Los Angeles Kings owner Bruce McNall, along with input from The Great One, that sent Wayne Gretzky from Edmonton to Los Angeles, along with Marty McSorley and Mike Krushelnyski. In return the Oilers received Jimmy Carson, Martin Gelinas, three first round draft picks and $15 million.
18 Florida Panthers
- Dan Boyle for 5th Rounder
17 Los Angeles Kings
- Kimmo Timonen and Jan Vopat for Future Considerations
Following the 1998 expansion draft, the Kings traded prospect Kimmo Timonen and Jan Vopat to the Nasvhille Predators for "future considerations". Under the terms of the pre-arranged deal the Predators received Timmonen and Vopat as compensation for taking goaltender Frederic Chabot in the expansion draft and not selecting defenseman Garry Galley.
16 Minnesota Wild
- Nick Leddy and Kim Johnsson for Cam Barker
At the 2010 trade deadline the Wild traded defense prospect Nick Leddy and 33-year-old defenseman Kim Johnsson to the Chicago Blackhawks for former third overall pick Cam Barker. Johnsson scored three points in eight games for the Blackhawks, but didn't play at all in the postseason during Chicago's Stanley Cup run. However, Leddy became a top four defenseman and was only traded from Chicago for salary cap reasons. He produced a career high 37 points for the New York Islanders in 2014-15.
15 Montreal Canadiens
- Patrick Roy and Mike Keane for Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko
Canadiens fans everywhere point to this trade as being the main reason for the Habs currently experiencing the longest Stanley Cup drought in the franchise's history. After being humiliated in a game against the Red Wings, in which Roy was kept in nets for nine goals, he stormed past coach Mario Tremblay and told team president Ronald Corey, "it's my last game in Montreal." Four days later, the team traded Roy and captain Mike Keane to Colorado for goaltender Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko.
The trade essentially handed the Avalanche the 1996 Stanley Cup while the Canadiens failed to get an impact player for an elite goalie with two Conn Smythe trophies to his name. It was bad enough that the Habs traded Roy, but to not get anything of value in return doomed the NHL's most storied franchise.
14 Nashville Predators
- Cody Franson and Matthew Lombardi for Brett Lebda, Robert Slaney and 4th Rounder
The Predators haven't made many bad trades in their short history, but their two worst trades happened to involve the same player. In the summer of 2011 the Predators traded Cody Franson and Matthew Lombardi to the Toronto Maple Leafs for Brett Lebda, Robert Slaney, and a fourth round draft pick in a deal that was made entirely for financial reasons. Lombardi had just completed the first year of a three year contract in which a concussion had limited him to just two games. In order to dump his contract, the Predators had to part with Franson.
13 New Jersey Devils
- Pat Verbeek for Sylvain Turgeon
12 New York Islanders
- Zdeno Chara, Bill Muckalt and 2nd Overall Pick (Jason Spezza) for Alexei Yashin
The Mike Milbury era was a fun time to be anyone but an Islanders fan. Milbury made a plethora of awful moves while running the Islanders, but his worst move came at the 2001 Draft when he acquired Alexei Yashin from the Ottawa Senators for future Norris Trophy winner Zdeno Chara, along with Bill Muckalt, and the second overall pick. Ottawa used the pick to draft Jason Spezza, who would post four 30 goal seasons and reach the 80 point mark four times with the Senators.
11 New York Rangers
- Rick Middleton for Ken Hodge
10 Ottawa Senators
- Pavol Demitra for Christer Olsson
In November of 1996, the Senators traded a 21-year-old centre named Pavol Demitra to the St. Louis Blues for defenseman Christer Olsson. Olsson played a total of 25 games for the Senators before returning to his native Sweden.
9 Philadelphia Flyers
- Peter Forsberg, Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, Chris Simon, two 1st Rounders and $15 Million for Eric Lindros
When the first overall pick in the 1991 NHL Draft, Eric Lindros, refused to play for the Quebec Nordiques, many teams were lining up to trade for "The Next One". The Flyers ended up winning the bidding war, dealing Peter Forsberg, Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, Chris Simon, two first round draft picks, and $15 million to the Nordiques for Lindros. Although he became the dominant power forward of his era and won the Hart Trophy following the 1994-95 season, Lindros' career was cut short by concussions and he was never able to bring a Stanley Cup back to Philadelphia.
8 Pittsburgh Penguins
- Markus Naslund for Alek Stojanov
7 San Jose Sharks
- Josh Gorges and 1st Rounder for Craig Rivet
Heading into the 2007 NHL trade deadline, the Sharks acquired 31-year-old defenseman and pending unrestricted free agent, Craig Rivet from the Montreal Canadiens for defenseman Josh Gorges and a first round draft pick. Rivet played 17 games for the Sharks that season, recording eight points, and was rewarded with a four-year, $14 million contract contract extension. However, he'd only play one of the four years in San Jose, before being traded to Buffalo.
6 St. Louis Blues
- Joe Mullen, Terry Johnson and Rik Wilson for Eddy Bears, Charles Bourgeois and Gino Cavallini
Joe Mullen already had a 92 point season under his belt and was in the midst of his third straight 40 goal season when the Blues shipped him, Terry Johnson, and Rik Wilson to the Calgary Flames for Eddy Beers, Charles Bourgeois, and Gino Cavallini in February of 1986.
5 Tampa Bay Lightning
- Brad Richards and Johan Holmqvist for Jussi Jokinen, Jeff Halpern, Mike Smith and 4th Rounder
Brad Richards, Martin St. Louis, and Vincent Lecavalier led the Lightning to the last Stanley Cup championship in the pre-salary cap era in 2004. However, in a salary cap world the trio's high-priced contracts prevented the Lightning from adding depth to their lineup and by 2008, the team came to grips with the fact that they would have to move one of them.
4 Toronto Maple Leafs
- Tuukka Rask for Andrew Raycroft
At the 2006 NHL Draft, Maple Leafs general manager John Ferguson, Jr. was looking for a starting goaltender. With 2006 World Junior Gold Medal winning goaltender Justin Pogge also in the system, Ferguson was willing to trade his top goaltending prospect, Tuukka Rask, to the Boston Bruins for Andrew Raycroft. Raycroft had struggled for the Bruins in the first season following the 2004-05 lockout, but the Maple Leafs were confident that the 2004 Calder Trophy winner could regain his form in Toronto. He didn't.
3 Vancouver Canucks
- Cam Neely and 1st Rounder for Barry Pederson
2 Washington Capitals
- Filip Forsberg for Martin Erat and Michael Latta
Filip Forsberg was a consensus top five pick heading into the 2012 NHL Draft, so it seemed like a steal to many observers when the Swede fell to the Capitals at the 11th pick. However, it took less than a year for the Capitals to fall out of love with Forsberg and at the 2013 trade deadline he was dealt to the Nashville Predators for a disgruntled Martin Erat and Michael Latta.
Erat scored just two goals in 62 games and zero points in four playoff games for the Capitals before he was traded again, while Latta had just one goal in 70 career games heading into the 2015-16 season.
1 Winnipeg Jets (Atlanta Thrashers)
- Braydon Coburn for Alexei Zhitnik
Prior to the move to Winnipeg, the demise of the Atlanta Thrashers was due in large part to management's inability to ice a winning team. However, their worst trade came in the lone season that they did qualify for the Stanley Cup Playoffs. Sitting in first place in the Southeast Division at the 2007 trade deadline, the Thrashers dealt rookie defenseman Braydon Coburn to the Philadelphia Flyers for 34-year-old Alexei Zhitnik.
Zhitnik began his tenure in Atlanta by posting 14 points in 18 games, but he was held scoreless in the team's first round sweep at the hands of the New York Rangers. Zhitnik was a complete disappointment the following season, resulting in the Thrashers buying out the remainder of his contract. Coburn, on the other hand, became a top pairing defenseman for the Flyers, where he played parts of nine seasons.
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