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The Biggest Regret In Every NHL Team's History

Everyone makes mistakes and has regrets, and that includes NHL teams. The NHL Draft, as well as trades, are often pure luck, but some mistakes as well as what could have been if the team had made a different decision are almost laughable. TheSportster has discussed this phenomenon before as well as articles dedicated to mistakes of many teams such as Montreal and Toronto, but mistakes go beyond historic teams. Even newer teams such as Columbus have their fair share of regrets. However, these regrets don't just apply to teams with long histories like the original six. Even teams like the Nashville Predators and the Minnesota Wild, who have only been around for less than 20 years, have made their shares of bad moves.

Big trades don't happen as often as they used to since we're now in a salary cap league, but teams still make mistakes when managing their teams and will continue to do so.

From bad trades to draft busts, some of these are just plain bad luck and some are laughable, but we're all human here. Here are some of the biggest regrets that ever NHL team wishes to forget. If you're a fan of these teams, you probably feel that way too.

30 Anaheim Ducks: Ryan Kesler's Contract

Sergei Belski-USA TODAY Sports

Ryan Kesler of Anaheim recently signed a six-year $41.25 million contract. Both analysts and fans agree that there are many flaws within the contract. The contract takes up a lot of cap space for a team already struggling with the salary cap, and it can be debated that the contract wasn’t worth it. Kesler is without a doubt a star in Anaheim, but Anaheim needs to improve many facets of their game.

29 Arizona Coyotes: Moving to Arizona

Matt Kartozian-USA TODAY Sports

Arizona is a desert, both literally and figuratively. The state is covered in deserts, and the hockey market is pretty much nonexistent. The Arizona Coyotes were originally the Winnipeg Jets (the current Jets were previously the Atlanta Thrashers) and moved to Arizona in 1996. The hockey markets between the two cities could not be more different. Few care about hockey in Arizona; it can be seen simply by watching their home games. In Winnipeg, they live and breathe hockey. Having Wayne Gretzky serve as head coach didn’t even help the team.

28 Boston Bruins: Trading Tyler Seguin

Sergei Belski-USA TODAY Sports

When Boston traded Tyler Seguin to the Dallas Stars in 2013, it was highly speculated that it was due to his off-ice behavior that created his party boy persona. Trading their second overall pick from the 2010 draft seemed like an incredibly stupid move, and it is fair to say it was indeed one on Boston’s part. Seguin set to prove Boston wrong when he entered Dallas. Seguin’s numbers have improved greatly across the board since playing for Dallas.

27 Buffalo Sabres: Drafting Marek Zagrapan in 2005

via hcorli.com

26 Calgary Flames: Drafting Daniel Tkaczuk in 1997

via missisaugasenators.com

25 Carolina Hurricanes: Drafting Igor Knyazev in 2001

via nhl.com

The Hurricanes, like the aforementioned Arizona Coyotes, moved to Raleigh from Hartford in 1997, but that's not what we're going with here. While they've had their problems, the 'Canes have found a way to make it work in North Carolina. We're going with a draft pick here.

Igor Knyazev was drafted 15th overall by the Carolina Hurricanes in 2001 and never played in the NHL. He was a promising pick after his gold medal performance with Team Russia in the 2001 World Championships, yet moved back to play in Russia after a brief stint with Carolina’s AHL affiliate, the Lowell Lock Monsters. Another classic waste of a first round pick and prolific players drafted after him include Mike Cammalleri and Tomas Plekanec.

24 Chicago Blackhawks: Trading Chris Chelios

via espn.com

The Blackhawks probably don’t have many regrets in recent memory due to their recent dominance, but some mistakes in their history definitely stand out. The Chris Chelios trade to Detroit during the 1998-99 season is one of them. Chelios was one of the most dominant players on the Blackhawks at the time, and claims he was not only shocked by the trade but wanted to stay in Chicago (his hometown team) for the rest of his career.

23 Colorado Avalanche: Trading Sandis Ozonlish

via sbnation.com

Often considered to be one of the worst trades in the history of the Colorado Avalanche organization, Colorado traded prolific defenseman Sandis Ozonlish to the Carolina Hurricanes in 2000. Ozonlish was one of the rare defensemen who were also dominant offensively, so it makes little sense as to why Colorado traded him, but it was for financial reasons.

22 Columbus Blue Jackets: Drafting Gilbert Brule in 2005

via sportsgraphs.com

21 Dallas Stars: Drafting Scott Glennie in 2009

via sportsgraphs.com

While the Minnesota North Stars had their share of mistakes, we'll stick with the Dallas Stars' time in Texas.

20 Detroit Red Wings: Drafting Max Nicastro in 2008

via orlandosolarbears.com

We could have possibly included the Wings trading Marcel Dionne but at the time, the Wings had to trade Dionne for financial reasons.

19 Edmonton Oilers: Trading Wayne Gretzky

via sportsnet.ca

The trade of Wayne Gretzky from the Edmonton Oilers to Los Angeles in 1988 is easily the most prolific trade in NHL history. After all, it is the only trade NHL that resulted in an ESPN 30 for 30 special. The trade shocked everyone, and some Oilers fans still haven’t forgiven their team for this atrocity. The trade ended up working out for both parties, as Edmonton won another Stanley Cup without Gretzky and the hockey world expanded to other parts of the United States with Gretzky’s presence.

18 Florida Panthers: Drafting Petr Taticek in 2002

via lepravha.cz

To be fair to the Florida Panthers, the 2002 NHL Draft wasn’t the best one, but they seriously blew their first round pick. They selected Petr Taticek for their ninth overall pick, who played only three NHL games with the Panthers. He was in and out of the minors awhile before returning to home to Europe, where he currently plays.

17 Los Angeles Kings: Dustin Brown's Contract

Kirby Lee-USA TODAY Sports

Dustin Brown captained the Kings to two Stanley Cups, so there is obviously some sentimentality when discussing Brown's situation with the Kings. However, Brown's offensive game has dropped off significantly since he was signed to an eight-year, $46 million contract extension. This was back in 2013 and Brown still has five years after this season to go on the contract. The Kings even stripped Brown of his captaincy last summer in favor of Anze Kopitar so it's clear they made a huge mistake here. That cap space could have been used to get the Kings a much needed scorer right now as they try to capture a third Stanley Cup.

16 Minnesota Wild: Drafting James Sheppard over Claude Giroux in 2006

via sbnation.com

To be fair to the Minnesota Wild, a lot of teams probably regret not picking up Claude Giroux (despite his mediocre season this year, he has been a very solid and prolific player throughout this career) at the 2006 NHL Draft, but Minnesota takes the cake. They drafted James Sheppard with the ninth overall pick, who played three mediocre seasons with Minnesota before being traded to San Jose for three seasons. San Jose eventually traded him to the New York Rangers, before he left the NHL to play in Europe.

15 Montreal Canadiens: Trading Patrick Roy

via sbnation.com

Trading Patrick Roy in the middle of the 1995-96 season was the beginning of the end of the Montreal Canadiens dominating the NHL, and they haven’t fully recovered since. One of the greatest goaltenders to ever play the game, Roy won all three of his Vezina trophies during his tenure in Montreal as well as two of his four Stanley Cups. He was an icon to the Canadiens. He was traded to Colorado after refusing to play another game for Montreal, due to a rift between him and Mario Tremblay, the head coach at the time. Roy went on to win two more Stanley Cups in Colorado while the Habs fell into a black hole.

14 Nashville Predators: Drafting Ryan Parent in 2005

via nhl.com

13 New Jersey Devils: Drafting Mattias Tedenby in 2008

via nhl.com

Most draft busts can be defended by the player having a good junior career and not adjusting well to the NHL, that is not the case for New Jersey’s first round (24th overall) pick in the 2008 NHL Draft. Mattias Tedenby had a mediocre amateur and professional hockey career across the board, it doesn’t make much sense why he was picked up in the first round. After several years of mediocrity as well as being in and out of the minors, Tedenby went back home to Sweden to continue his career (yes, it’s still pretty mediocre). This is the epitome of a waste of a first round draft pick.

12 New York Islanders: Hiring Mike Milbury As GM

via hockeyworldblog.com

11 New York Rangers: Drafting Hugh Jessiman in 2003

via nytimes.com

One of the most embarrassing draft busts for the New York Rangers, they drafted Hugh Jessiman as their 12th overall pick in 2003 and regretted it almost immediately. He never laced up his skates for the Rangers and remained in the minors for several years after graduating Dartmouth in 2005. He eventually made his NHL debut in in the 2010-11 season for the Florida Panthers, but only played two games. The most embarrassing aspect of this bust are the successful NHL players the Rangers could have taken.

10 Ottawa Senators: Drafting Brian Lee over Anze Kopitar in 2005

via senators.com

9 Philadelphia Flyers: Trading Sergei Bobrovsky

Aaron Doster-USA TODAY Sports

Sergei Bobrovksy has shined this season as the goaltender for the Columbus Blue Jackets, who have had a breakout season with their sixteen game win streak. Bobrovsky has become one of the most prolific goalies in the NHL, it’s hard to believe that the Philadelphia Flyers traded him back in 2012. To be fair to Philadelphia, Bobrovsky wasn’t the beast he is today back then, but he was still a promising young goaltender.

8 Pittsburgh Penguins: Drafting Jordan Staal over Jonathan Toews in 2006

Kim Klement-USA TODAY Sports

Pittsburgh choosing Jordan Staal with their second overall pick in the 2006 NHL Draft seemed like a good idea at the time. Looking back, it wasn’t the best decision, especially since Jonathan Toews was selected right after Staal by Chicago. The Chicago Blackhawks are the only team in the NHL who have achieved a modern dynasty, and imagining him in Pittsburgh (especially with Crosby and Malkin) means there is a good chance Pittsburgh would be today’s dynasty if they selected him in the draft.

7 St. Louis Blues: Firing Joel Quenneville

Jasen Vinlove-USA TODAY Sports

It is no secret that Joel Quenneville is one of the most successful head coaches in the NHL, making it hard to believe that any team would ever fire him. In 2004, he was fired from his position as head coach of the St. Louis Blues. To add even more salt in the wound for St. Louis, Quenneville was hired as head coach for the Chicago Blackhawks (one of their biggest rivals) in 2008. He has since won three Stanley Cups with them since 2010.

6 San Jose Sharks: Drafting Teemu Riihijarvi in 1995

via greatesthockeylegends.com

The 1995 NHL Draft is often regarded as one of the worst drafts in the history of the league. Most drafts have several standout players, and the two best players 1995 had to offer were Shane Doan and Jarome Iginla. I’m not saying they’re bad players, but only having two players truly stand out at the draft is kind of embarrassing for the NHL as a whole.

5 Tampa Bay Lightning: Drafting Alexander Svitov

via si.com

Tampa Bay has surprisingly not made many mistakes in their 25-year history, but this is a big one. Back in 2001, the Lightning were in full-on rebuild mode and had the chance to get a true blue chip prospect with their third overall pick. While Ilya Kovalchuk and Jason Spezza were off the board, the Lightning could have done better than Alexander Svitov with the third overall pick. Svitov turned out to be one of the biggest busts in NHL history while some very good players were drafted after him. Among the players Tampa could have had include Miikko Koivu, Patrick Sharp, Mike Smith and Ales Hemsky.

4 Toronto Maple Leafs: Trading Their 1991 First Rounder

via canada.com

Some NHL players are just impossible not to love. Scott Niedermayer was one of them. He was one of the best defensemen of his generation and he led multiple teams to the Stanley Cup. One of those teams could have been the Toronto Maple Leafs, but the Leafs traded their first round pick in 1991 which could have been used to take Niedermayer. Instead, the Leafs got Tom Kurvers in the trade, who would only play 89 games with the Leafs before they traded him to the Canucks.

3 Vancouver Canucks: Not Closing The Deal On The Great One

via sportsnet.ca

Trading away a young Cam Neely was definitely considered here, but when you have a chance to get Wayne Gretzky and you blow it, that's very embarrassing as a franchise. The story goes that back in 1996, Gretzky had agreed with Pat Quinn in principle in coming to the Canucks. They spoke at night and Gretzky informed Quinn that he would sign the papers in the morning after his agent looked at them. Unfortunately, the Cancuks' meddlesome owner ordered Quinn to close the deal that very night. Quinn called Gretzky insisting he had to sign immediately. The situation turned Gretzky off and he ended up signing with the Rangers instead.

While Gretzky's best days were behind him, you show us one Canucks fan who isn't embarrassed after hearing this story.

2 Washington Capitals: Trading Filip Forsberg

Kim Klement-USA TODAY Sports

Capitals GM Brian MacLellan even admits that this one was a mistake. Filip Forsberg was drafted 11th overall by Washington in the 2012 NHL Draft, but never got to lace up his skates as a Capital. He was traded to Nashville in 2013 for Martin Erat and Michael Latta. Neither players still play for the Capitals, yet Nashville greatly benefitted from the trade as Forsberg is one of their strongest forwards.

1 Winnipeg Jets: Not Drafting Braden Holtby in 2008

Geoff Burke-USA TODAY Sports

Back when they were the Atlanta Thrashers in 2008, the Winnipeg Jets (along with every other NHL team except Washington) had the chance to draft 2016 Vezina Trophy winner Braden Holtby. Judging by their mediocrity in the goaltending department, this is something they probably regret. They drafted Danick Paquette in the third round of the 2008 NHL draft, who never played in the NHL. Braden Holtby didn’t go to Washington until the fourth round. Drafting Holtby could have solved all of their goaltending problems, and although most NHL teams probably regret not drafting Holtby, it must sting the most with Winnipeg since they blew their third round pick.

Holtby remains one of the league's top goaltenders while Winnipeg is still searching for a long-term answer in nets.

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The Biggest Regret In Every NHL Team's History