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The Biggest Regret In Every NHL Team's History

From bad trades to draft busts, some of these are just plain bad luck and some are laughable.

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.

This contract is making the improvements rather difficult to make. The cap space taken up by this contract make it hard to sign on and lock in new players to help improve the team. This contract is keeping the team from growing, something the Ducks are definitely regretting. You have to wonder if it will hurt their Cup chances for the next few years.

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.

It is safe to say that if you could give the Arizona Coyotes a time machine, they would probably choose to remain in Winnipeg, or at least move to a U.S. market with a richer hockey history.

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.

Since Seguin’s departure, Boston has yet to enter the Stanley Cup Final, something they achieved twice during Seguin’s tenure as well as one championship. They've also missed the playoffs the last two seasons and are in danger of missing it again this year. That could be karma talking, but there is no doubt that Boston regrets this decision.

27 Buffalo Sabres: Drafting Marek Zagrapan in 2005

via hcorli.com

Buffalo wasted their first round (13th overall) draft pick in 2005 on Marek Zagrapan. Zagrapan has never played in the NHL. 2005 was a big year in the draft, with big names such as Sidney Crosby and Anze Kopitar. Many prolific players of today were picked after Zagrapan such as TJ Oshie, Tuukka Rask, James Neal, Kris Letang, Jonathan Quick, Niklas Hjalmarsson and Ben Bishop. All of these players would have been a much wiser choice. The management at Buffalo is probably still shaking their heads to this day over this choice, especially with their struggles in recent years and how many great players they let slip away.

26 Calgary Flames: Drafting Daniel Tkaczuk in 1997

via missisaugasenators.com

Daniel Tkaczuk was drafted sixth overall in the 1997 NHL Draft by the Calgary Flames. He played a total of 19 games in his NHL career, which is so far below what is expected of someone drafted sixth overall that it’s almost laughable. It is safe to say it was a wasted pick. One of the most prolific players drafted after Tkaczuk was Marian Hossa, one of the few active players in the NHL destined for the Hockey Hall of Fame. This is one of the most embarrassing draft busts out there, and one that Calgary certainly regrets. The 1997 class wasn't the most star studded group, but just imagine what the Flames could have had if they took Hossa. Could you imagine teaming him up with Jarome Iginla in Calgary?

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.

Knyazev has not had a successful career in Russia by any means, so it is probably best that he never played in the NHL.

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.

The trade seemed to work out for Chelios and stung Chicago when he won two Stanley Cups with Detroit in 2002 and 2008. If the Blackhawks had held onto Chelios, their dynasty easily could have begun earlier, which is a pretty tough reality to swallow. It also would have been nice to see him win a championship with the Hawks.

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.

The embarrassing aspect of the trade was the outcome since every player acquired from the trade did nothing to help out Colorado and left shortly after their arrival. Among the players acquired were Nolan Pratt and draft picks that turned out to be Václav Nedorost, Jared Aulin, and Agris Saviels. Trades are supposed to help both parties in the long run, and that wasn’t the case for this trade.

22 Columbus Blue Jackets: Drafting Gilbert Brule in 2005

via sportsgraphs.com

Columbus is one of the newer teams in the NHL and has had their fair share of bad draft picks. It's part of why they've yet to win a playoff series in their entire history. Among their bad picks, Gilbert Brule is the worst of them. Columbus drafted Brule sixth overall in the 2005 NHL Draft. Brule’s career was mediocre at best and spent the majority of his NHL career (he also played for Edmonton and Phoenix) in and out of the minors. He left the NHL for good in 2014 and now plays in the KHL. What makes this waste of a first round particularly embarrassing are the players drafted after him that Columbus could have taken including Anze Kopitar, T.J. Oshie, and much more.

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.

The Dallas Stars drafted Scott Glennie eighth overall in the 2009 NHL Draft and since he has only played one NHL game (back in the 2011-12 season), it is safe to say that it was a waste of a first round pick. To be fair to Dallas, the 2009 draft wasn’t the most star-studded draft out there, but Glennie’s career in the AHL has been rather mediocre, so it still could have been a bust if he played in the NHL for the majority of his professional career. With an impressive career in the WHL, he seemed like a good pick but hasn’t come close to replicating the points he produced back in the day.

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.

Most of the draft busts on the lists were drafted in the first round and the Detroit Red Wings drafted Max Nicastro in the third round (91st overall) in the 2008 NHL Draft. What makes Max Nicastro’s case unique is he was given a second chance after charges against him in from a sexual assault case from his time at Boston University (where he played for four years after he was drafted) were dropped in 2012. He refused to take advantage of the second chance and went on the have a career in the minors that could be considered mediocre at best.

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.

The regret among the Oilers is that if Gretzky had stayed, they could have won many more Stanley Cups. The fans that are still bitter nearly three decades later are also something they wish they could get rid of.

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.

It is probably a better fit for Taticek since his numbers are much better across the board in Europe than they were in North America, but that probably doesn’t make the Panthers feel much better after wasting a first round pick. Prolific players drafted after Taticek include Duncan Keith and Cam Ward. You wonder why the Panthers endured a 12-year playoff drought between 2000 and 2012? It was because of moves like this.

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.

Brown's contract is virtually immovable, so you wonder if the Kings will eventually bite the bullet and buy him out.

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.

What makes this draft bust unique is the haunting possibility of what could have been if Minnesota had selected Claude Giroux of the Philadelphia Flyers (who was selected 22nd overall) in the 2006 draft.

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.

Both Mario Tremblay and the Montreal Canadiens as a whole never fully recovered from the incident.

14 Nashville Predators: Drafting Ryan Parent in 2005

via nhl.com

The 2005 NHL Draft was one of the most star-studded in recent history, and Nashville had the perfect opportunity with their 18th overall pick. Instead, they drafted Ryan Parent. Parent never laced up his skates for Nashville but played with their AHL affiliate, the Milwaukee Admirals, for ten games without earning a single point. He moved onto other minor league teams and played for other NHL teams (he was in and out of the minors for his entire NHL career) such as the Philadelphia Flyers and Vancouver careers. His entire professional career has been mediocre at best and hasn’t played in the NHL since the 2010-11 season. Needless to say, this was a bad bust for Nashville. Several quality players were drafted after Parent, including T.J. Oshie and Tuukka Rask, and that was in the first round alone.

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.

The Devils made plenty of great moves during the Lou Lamoriello era, but this was clearly not one of them.

12 New York Islanders: Hiring Mike Milbury As GM

via hockeyworldblog.com

Why would we put the hiring of a GM as the Islanders' worst regret? Well because Mike Milbury was just about the worst GM in the history of hockey. In his tenure as Islanders GM, Milbury traded away Roberto Luongo to replace him with Rick DiPietro, Zdeno Chara and a second overall pick (Jason Spezza) for Alexei Yashin and trading other young players who would go on to be stars in the NHL. It was clear Milbury was not cut out to be the GM and his hiring sent the Islanders into a tailspin as an organization. The Islanders may have recently ended a 23-year playoff series win drought, but they're still not what you'd call a model franchise.

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.

This list includes Dustin Brown,, Brent Seabrook, Zach Parise, Ryan Getzlaf, Ryan Kesler, Brent Burns, Corey Perry and Patrick Eaves. To make it worse, the list goes on. Those are the successful players picked after Jessiman in the first round alone.

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

via senators.com

The Ottawa Senators had the ninth pick overall in the 2005 NHL draft and went with Brian Lee. Lee did not make his NHL debut with the Senators until the 2007-08 season and was mediocre at best. He spent his career with the Senators and Tampa Bay Lightning before retiring after the 2012-13 season. This seems like one of the less embarrassing draft busts on the list, but what makes this truly embarrassing is that two-time Stanley Cup winner and Los Angeles Kings captain Anze Kopitar was drafted two picks later. If the Senators had drafted Kopitar that year, it is safe to say that the team would be completely different than it is today. They'd probably have a Stanley Cup or two under their belt.

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.

With Philadelphia currently struggling to qualify for the playoffs as well as struggling with goaltending, they probably regret getting rid of Bobrovsky. Unfortunately for Philadelphia, the feeling probably isn’t mutual for Bobrovsky. Goaltending has plagued the Flyers for so long so it's painful to think the long term answer was right there in their organization and they let him slip away.

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.

Although Staal was a good player, he did not meet expectations (unlike Toews, who exceeded them) and was traded to the Carolina Hurricanes in 2012. As deep as Pittsburgh is at center today, they would have had the deepest depth chart at center ice in NHL history.

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.

Since the Blues have never won a Cup and Quenneville was arguably one of their best coaches (next to Ken Hitchcock, who they recently fired), it can be easily said that they regret this decision. Heck, the season after they fired Quenneville, the Blues finished last in the league.

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.

Only one player selected in the first round never played in the NHL, and that was San Jose’s 12th overall pick, Teemu Riihijarvi. Riihijarvi had a less than stellar career in Europe, so it is probably best that he never laced up his skates for San Jose, but it’s still pretty embarrassing to waste a first round pick like that.

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.

If the Lightning had taken any of these players, they probably wouldn't have experienced the franchise slump they did after their 2004 Stanley Cup.

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.

Niedermayer's best years came when Toronto was a perennial playoff team in the late 90s and early 2000s but couldn't get over the hump and win a Stanley Cup. Niedermayer likely would have been the missing piece they needed.

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.

To add more salt to the wound, Forsberg is only 22 and has his entire NHL career ahead of him and Washington simply blew it by letting him go. While Washington is still the most stacked team in the NHL, just imagine where they could have been if they had kept Forsberg. He could have been their missing piece.

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