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50 Worst Things in NHL History

Tom Urtz Jr.Contributor IJanuary 15, 2017

50 Worst Things in NHL History

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    NHL hockey may be one of the greatest sports in the entire world, but not everything has been great over the years. Throughout the history of the league, there have been terrible moments, incidents, jerseys, players, officials, draft picks, missed calls, trades, free-agent signings and so on.

    The impending lockout is another thing that can be added to this list of misdoings so without further notice, let's take a walk down memory lane as we look at 50 of the worst "things" in NHL history.

Dallas Stars Take the Bull by the Horns

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    Sometimes there are just concepts for NHL uniforms that sound great as an abstract concept, but once they are back from the presses, the designer finally realizes their huge mistake.

    This jersey sums up a good idea gone wrong. The Dallas Stars though they were doing a good thing featuring a bull on their jersey because of the association of bull riding in Texas.

    However, the astrological element of Taurus and the coloring really make a bad jersey 10 times worse. This is easily one of the worst uniforms in NHL history.

Trent McLeary Has Windpipe Crushed and Career Ended

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    This video is hard to watch, so use your discretion. During a game against the Philadelphia Flyers, Montreal Canadiens player Trent McCleary dropped down to block a shot. As a result, the puck hit McCleary directly in the throat, crushing his windpipe.

    When he was carried off the ice, he lost consciousness and was rushed to a hospital where he was put on oxygen. Unfortunately, this was the last game of McCleary's career and it is known as one of the worst injuries in NHL history.

The Accidental Death of Bill Masterton

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    Bill Masterton was a player for the California Golden Seals and was one of the first players who died as a direct result from a hockey injury. During a game, Masterton was hit when he had the puck and he would bang his head on the ice.

    Masterton started to bleed, and he eventually was hospitalized and died after suffering a brain hemorrhage. 

New York Islanders Fisherman Jersey

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    The New York Islanders are a team that has a rich history and they happened to be one of the most dominant teams in the 1980s.

    When you look at the Isles' current jerseys, they are one of the league's best because it is a clean and simple design that represents their colors.

    However, when the Islanders wore a jersey featuring a logo that happens to resemble the Gorton's Fisherman, the Islanders were called the Fish Sticks by detractors. 

    The jeer made sense considering the success of the team at the time and the jerseys they wore night in and night out.

Mike Milbury

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    Mike Milbury will go down as one of the worst general managers in NHL history for the trades he made and the terrible contracts he helped orchestrate.

    Here is a short list of the talent Milbury shipped out while he was at the helm in Long Island.

    • Zdeno Chara
    • Roberto Luongo
    • Olli Jokinen
    • Chris Osgood
    • First-round draft pick that became Jason Spezza
    • Bryan Berard 

    The list goes on and on and when you look at the contracts handed to Rick DiPietro and Alexei Yashin under his watch, it isn't a surprise that the Islanders have wallowed in the bottom of the Eastern Conference for most of the last decade.

Clint Malarchuk's Terrible Injury

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    In the history of the NHL, this is probably one of the worst injuries suffered during a game.

    Clint Malarchuk was a goaltender for the Buffalo Sabres, and during a 1989 game, his jugular vein was slashed by an opponent's skate during a collision in the crease.  

    Within seconds, Malarchuk was in a pool of his own blood. Fortunately, the Sabres medical staff was top notch and they were able to sustain Malarchuk's condition until doctors arrived to treat the wound that required over 300 stitches.

Detroit Red Wings Trade Marcel Dionne

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    Marcel Dionne was one of the greatest players in the history of the Los Angeles Kings, a team he spent 12 years with. During that time, Dionne recorded six 50-goal seasons. However, this wouldn't have been possible if the Detroit Red Wings hadn't traded him to Los Angeles in a lopsided deal.

    Dionne was traded to the Los Angeles Kings in along with teammate Bart Crashley in exchange for Dan Maloney, Terry Harper and a second-round draft choice.

    As history proved, this was a terrible trade for the Wings.

Flying V

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    This jersey was a flying "v" but it probably isn't the flying "v" you were thinking of. The "v" on the jersey easily is identifiable with the team's location in Vancouver but other than that, there really isn't much sense to this jersey.

    Strangely enough, although the jersey is rather hideous, the developers at EA Sports still include this as a throwback jersey for the Canucks in every edition of the NHL video game series.

Alexei Yashin's Contract with the New York Islanders

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    Alexei Yashin's contract with the New York Islanders was one of the worst in NHL history and it still sits on the team's salary cap today.

    Yashin was signed to a mega-deal worth $71,597,944 over 10 years. The Russian forward never replicated the success he had with the Ottawa Senators, and his contract was bought out by the Islanders.

Wayne Gretzky's Missed High Stick on Doug Gilmour

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    This moment is one of the worst missed calls in NHL history and it was blatantly obvious from the moment it happened.

    Doug Gilmour was high-sticked by Wayne Gretzky and was knocked to the ice. When the play was whistled off, Kerry Fraser failed to call a penalty even though Gretzky looked guiltier than sin.

    As " luck" would have it, Gretzky went on to score a game-winning-goal when he should have been sitting in the penalty box.

    Toronto Maple Leafs fans will likely never forgive Fraser for a call that changed the fate of the team's history.

Chris Simon Cheapshots Ryan Hollweg

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    This is one of the worst cheap shots in recent memory, and it isn't a coincidence that Chris Simon is no longer in the NHL.

    Chris Simon was a goon who attempted to inflict bodily harm on opponents during his short-lived NHL career.

    This moment was dirty and uncalled for and Hollweg could have been really injured.

    Hollweg and Simon had been physical towards each other all night long, but there was no reason for Simon to hit Hollweg in the head with his stick.

Boston Bruins Return in the Joe Thornton Trade

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    When the Boston Bruins traded their captain and perennial All-Star forward to the San Jose Sharks, it was major news that shocked the NHL. When looking back on the return the Bruins got for their captain, it isn't hard to see why they struggled for a little while after the trade.

    A return of Brad Stuart (now back with San Jose), Marco Sturm and Wayne Primeau was not hardly enough for Thornton, who has gone on to post multiple 80- and 90-point seasons in San Jose, including 92 points in 58 games the year he was traded.

Calgary Flames' Donkey Jersey

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    It is understood that the team has flames in its name, but where does the donkey come into play?

    This logo made zero sense for the team and it is a huge mystery why the jersey existed in the NHL for eight seasons before it was unceremoniously retired.

    This concept could have been so much better, but finally the team came to their senses and started wearing a modified version of an old Atlanta Flames jersey as a primary alternate.

Brett Hull Dealt by Calgary Flames

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    While we are on the subject of the Calgary Flames, let's look at one of the worst trades made in NHL history. 

    The "Golden Brett" was off to an amazing start to his first full NHL season in 1987-88 and he had recorded 50 points in 52 games.

    However, the Flames decided to trade Hull and the rest is history. By history, I am referring to the 715 goals and the 625 assists recorded by Hull for a grand total of 1,340 points after being traded by the Flames.

    Hull also went on to win two Stanley Cups, a Hart Trophy and Lester Pearson Award, so it is safe to say that Calgary really made a horrendous mistake in dealing Hull. 

Marty McSorley Incident

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    When this happened live on Feb. 21, 2000, the fans in attendance were horrified.

    Something this intentionally violent was rare for the NHL, and there was widespread concern for Donald Brashear after he suffered a severe concussion.

    Marty McSorley was sentenced to 18 months probation for assault and he was suspended one calendar year by the NHL. He never played another game in the NHL.

The Death of Brittanie Cecil

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    Back in 2002, a young Columbus Blue Jackets fan named Brittanie Cecil died after being struck by a puck in the head.

    When the event happened during the game, it was horrifying and very frightening for the fans in attendance. Her death prompted a huge change in arena safety, and the NHL expanded the safety nets in the arena to better protect fans.

Buffalo Sabres' Buffaslug

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    The Buffalo Sabres were one of the NHL's top teams coming out of the lockout and they boasted a lineup that featured Daniel Briere, Chris Drury, Jason Pominville, Derek Roy and Thomas Vanek. Despite the team's top play, they had one of the league's worst jerseys.

    This jersey became known as the Buffaslug because it featured a slug-like body with a Buffalo head. It was one of the worst jerseys in NHL history, so the team was right to abandon it when they did.

String of Hockey-Player Deaths in 2011

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    The hockey world lost Derek Boogaard, Wade Belak, Tom Cavanagh and Rick Rypien during the year 2011.

    It was a string of deaths that truly shocked the world and it really hit the fans hard. Boogaard accidentally overdosed on prescription painkillers, and the news got worse when more information was revealed.

    It became ever more of a tragedy when the New York Times released a multi-part series detailing Derek's condition. It got worse when news came out that Boogaard's own brother and NHL teams were enabling him with his drug addiction.

    That summer, the NHL also lost Rick Rypien and Wade Belak, two players who had battled personal issues and demons, and they ultimately took their own lives. Earlier in the year, young forward Tom Cavanagh of the San Jose Sharks took his own life.

    The deaths of Boogaard, Belak, Cavanagh and Rypien cast a dark cloud over the NHL and it is looked back on as one of the worst string of tragedies in NHL history.

Terrible Goal Call During Winnipeg Jets vs. Chicago Blackhawks Game

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    It is hard to believe that this ludicrous goal was awarded to the Winnipeg Jets and many still can't believe that the Jets got away with this.

    When the decision was announced, Coach Suter was very frustrated and peeved.

    So he did what any calm, collected, and level-headed coach would do in a situation like this, he climbed over the bench and he ran across the ice to confront the referee over his decision.

    I still have no idea how this happened, and I guess no one ever will know. 

Max Pacioretty's Frightening Neck Injury

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    During the 2010-11 season, Max Pacioretty suffered one of the worst injuries in NHL history, and it was a catalyst for many safety changes in NHL rinks around the league.

    Pacioretty missed the end of the 2010-11 season after he was run into a stanchion on a hit delivered by Zdeno Chara. He suffered a fractured vertebrae and a severe concussion as a result and it didn't appear like he would be able to return.

    Chara received a five-minute major and a game misconduct, but no suspension for the hit. 

Tim Thomas and Facebook Saga

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    During the 2011-12 season, Tim Thomas snubbed President Obama by not visiting the White House with the rest of his Boston Bruins teammates. After this incident, reporters pestered Thomas about his Facebook posts. 

    Thomas finally had enough with the string of terrible press conferences and he finally walked out on reporters.

    The Bruins netminder is taking a sabbatical from the 2012-13 season if there is no hockey to be played, so maybe this news will finally die down once and for all.

Tampa Bay Lightning Are on Fire?

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    Currently, the Tampa Bay Lightning have one of the simplest and cleanest looks in the league. Back when the team was founded, the same could not be said about their uniforms.

    This incarnation did not last long because it was deemed to be a bit much and eventually the team dropped the flames, and Lightning word mark and featured a big lightning bolt with Tampa Bay on top.

    This remains one of the worst alternate jerseys in NHL history but at least the team recognized that a change needed to be made sooner rather than later.

The Wayne Gretzky Trade from the Edmonton Oilers Perspective

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    The trade of Wayne Gretzky from the Edmonton Oilers to the Los Angeles Kings will always be viewed as one of the most important trades and one of the worst trades in NHL history.

    It was one of the worst trades because Peter Pocklington basically made a back-alley deal to trade his franchise star because of financial problems.

    When looking at the Oilers' return in the trade at the time, it appeared to be a decent return highlighted by prolific scorer Jimmy Carson but as history has told us, he didn't last long in Edmonton. During his first two years in the NHL, Carson tallied 92 goals and 186 points.

    He was producing at a solid pace for the Kings, and he was a key piece in the Wayne Gretzky blockbuster trade. However, Carson couldn't live up to the pressure of being the man to replace Wayne Gretzky, and he eventually was traded to the Detroit Red Wings before winding up back in L.A.

The Shootout

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    This is another element of hockey that was put into action after the 2004-05 lockout and it really cheapens the game. In the old days, if two teams were tied after overtime, the game would end a tie and each team earned a point.

    However, in an attempt to increase scoring and interest in the league, the shootout gimmick was put into existence. This is something that really takes the thrill out of intense games because after 65:00 of intense action, a game could be decided by a simple penalty shot.

Phoenix Coyotes Desert Dog Jersey

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    This jersey looks like it belongs in a video game and not one related with the NHL. The coyote featured on jersey appears to be half coyote and half robot and that really doesn't make any more sense than the moon and cacti featured in a night sky on the bottom of the jersey.

    This jersey was an utter abomination and something that should have never seen the light of day.

Bryan Trottier as the Head Coach of the New York Rangers

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    The hiring of Bryan Trottier was one of the worst and strangest moves by Glen Sather in the history of his tenure with the New York Rangers.

    Trottier got the job after impressing Slats with a 93-page handwritten application but the experiment only lasted 54 games in which the Rangers went 21-26-6-1.

    Although Trottier was an amazing goal scorer and player, he was one of the worst coaches in NHL history.

The Calgary Flames Are Robbed in 2004 Stanley Cup Final

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    MartIn Gelinas and the Calgary Flames were robbed during the Stanley Cup Final because there was no formal video review on an apparent goal during a crucial Game 6 in Calgary.

    This video clearly shows from 5:15-5:17 that the puck is in the net.

    Had this goal counted, the Flames could have won the Stanley Cup that night. However, many feel that the Calgary Flames were robbed.

    Looking at the evidence it is safe to say that this non-call changed history for both sides involved.

Pittsburgh Penguins Foolishly Trade Markus Naslund

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    Markus Naslund had a pretty decent career as a member of the Vancouver Canucks and the New York Rangers after being dealt by the Pittsburgh Penguins for a player by the name of Alex Stojanov. 

    When Naslund hung up his skates, he had amassed 869 points in 1,117 career games. Stojanov on the other hand, played only 45 games with the Penguins and managed to produce six points.

    The Penguins made a bad trade but their dominance in the 1990s with Jaromir Jagr and Mario Lemieux likely lessened this blow.

Raffi Torres Stoops to an All-Time Low

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    Everyone in the world saw this hit except the on-ice officials. Marian Hossa was blatantly hit with a cheap shot by Raffi Torres of the Phoenix Coyotes.

    Hossa was attempting to move the puck, and Torres left his feet as he lunged into the prone Hossa. As a result, both players' postseasons were over, but Hossa ended up in the hospital and Torres ended up in the press box.

Lack of Synced Clocks Cause Kerfuffle During Rangers-Caps Series

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    The lack of synced clocks in NHL arenas has had an impact on many different games. This moment was a precursor of worse things to come when it comes to clocks and goals allowed or disallowed.

    The New York Rangers appeared to have scored a goal but the official clock was not in sync with the clock on NBC. 

    By mere sight, this appeared to be a goal but video review proved to disallow this goal.

    Nonetheless, Rangers fans were very peeved, and it all could have been avoided if the clocks were right.

Another Faulty Clock

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    This terrible goal-call moment is pretty self-explanatory. Take a look at the official game clock in the bottom left-hand corner, notice the stoppage and then count down until the puck crosses the net.

    This was a brutal call that received months of debate by those involved.

Steve Moore Incident

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    This moment in 2004 still lives in infamy as one of the worst moments in NHL history because it had nothing to do with hockey. Steve Moore suffered a concussion and three fractured vertebrae in his neck, ending his NHL career. 

    Todd Bertuzzi served a 20-game suspension, the fourth longest in NHL history at the time. 

    The incident led to years of banter in courts between those involved. There were also claims that this was a retaliatory incident on Bertuzzi's behalf after Moore previously went after Markus Naslund.

    No matter how you look at it, this moment gave the league a huge black eye.

Toronto Maple Leafs Trade Draft Pick That Became Scott Niedermayer

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    During the 1989-90 season, the Toronto Maple Leafs traded their first-round pick in the upcoming 1991 NHL entry draft to the New Jersey Devils.

    In exchange they received a defenseman named Tom Kervers who spent a little over a season in Toronto.

    Fast forward to the 1991 draft and the New Jersey Devils selected future Hall of Fame defenseman Scott Niedermayer.

    This is looked at as a terrible trade because although the Leafs couldn't predict Niedermayer being drafted where he was, they still wasted a pick on a player who was sent out of town after a season.

Bryan Berard Is Almost Blinded

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    The 1997 Calder Trophy recipient, Bryan Berard, almost lost his eye because of an injury sustained early in his career.

    During a game against the Ottawa Senators, Berard was struck in the eye with an errant wild stick as a Senator attempted to shoot the puck. The ensuing footage is hard to watch, so viewers' discretion is advised.

The Lokomotiv Yaroslavl Tragedy

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    It is hard to believe that it has been a year since the hockey world suffered one of the worst tragedies in recent memory.

    The NHL community wept for all those lost in the plane crash that carried KHL team Lokomotiv Yaroslavl. The plane did not gain sufficient lift and crashed 1.5 miles from the runway.

    On the roster of the team were several former NHL players. Some of the recent NHL players who passed away in this tragedy were Pavol Demitra, Josef Vasicek, Karel Rachunek, Ruslan Salei, Karlis Skrastins and Alexander Vasyunov. 

    The team's bench boss was Brad McCrimmon, who was a journeyman in the NHL but found success when he won a Stanley Cup with the Calgary Flames.

    This moment will go down as one of the most frightening in NHL history because no one ever thinks that an entire team can be wiped away at one moment.

    It becomes even harder to come to terms with this tragedy when it was revealed that the flight crew wasn't even allowed to legally fly the plane.

The 1974-75 Washington Capitals

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    The 1974-75 Washington Capitals are the worst team in NHL history, and it isn't even close. The Caps currently hold the record for the worst overall finish in the history of the NHL.

    During the 74-75 campaign, the Caps went 8-67-5 with a grand total of 21 points. Looking back, this is a feat that likely won't be replicated anytime soon.

Bob Goodenow

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    Bob Goodenow was one of the worst NHLPA directors in the history of the league. Goodenow was an executive for the NHLPA and he was in office during the 1994 labor strike and the 2004-05 lockout.

    Goodenow ultimately resigned after the 2004-05 lockout and it probably had to do with his role in agreeing to a 24 percent rollback in player salaries.

The 2004-05 Lockout

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    The 2004-05 lockout was one of the worst things in NHL history because it took the league some time to recover after the dust had settled. Although the NHL has the greatest fans in the world, the fanbases were very hurt after a year of hockey went unplayed.

    The sport took a long time to take off again in the United States, and it appears that the NHL is going to have to earn back the trust of fans once again.

Florida Panthers and Columbus Blue Jackets Alternate Jersey

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    These two sweaters are among the worst in NHL history because they are a direct knockoff of the Pittsburgh Penguins jersey from the inaugural Winter Classic.

    If you Google all three jerseys and look at them side-by-side, it is pretty clear that the Penguins were ripped off.

    The Penguins were able to slightly pull it off, but the off-blue jersey color with a circular logo is pretty bland if you ask most fans.

Ottawa Senators Select Alexander Daigle

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    This pick by the Ottawa Senators busted so bad, whenever there is a top-tier and can't-miss prospect, critics always bring up the strange case of Alexander Daigle.

    He was hyped to be a top player who you could build your franchise around, but his NHL career only lasted 616 games and his best season topped out at a whopping 51 points.

    Daigle is looked back at as one of the worst first-round picks in NHL history.

Rick DiPietro's Contract

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    Rick DiPietro was signed to a 15-year contract six years ago and he has not even come close to living up to the deal he signed.

    He was a top-touted prospect, and the Islanders planned to build around DiPietro in the crease after he went No. 1 overall in the 2000 NHL entry draft.

    DiPietro has never managed to stay healthy and for that reason, he has one of the worst contracts in league history. After appearing in 63 and 62 games in the 06-07 and 07-08 seasons, DiPietro has appeared in only 51 games when you combine seasons 08-09 to the present.

    It is easy to feel bad for a guy like DiPietro because he isn't living out his dream, but then you need to remember that he is collecting money to do virtually nothing.

California Golden Seals Uniforms

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    There isn't much to say about this terrible uniform but as a die-hard hockey fan, on first glance there is something that strikes you as odd. Under no circumstances should a team combine teal, yellow and white on uniforms.

    It didn't help matters when the team name was the Golden Seals, so these uniforms just remind fans of one of the worst times in hockey history.

Philadelphia Flyers Trade for Eric Lindros

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    Eric Lindros had the potential to be the next big thing in the NHL, but injuries prevented him from making a lasting and significant impact.

    When the Philadelphia Flyers traded for Lindros, they gave up a huge package that really laid the groundwork for the Quebec Nordiques/Colorado Avalanche to become a powerhouse.

    The trade sent was centered around Peter Forsberg, Ron Hextall and a first-round draft pick that later became a key piece in acquiring Patrick Roy.

    Forsberg and Roy went on to win two Stanley Cups with Colorado, and Lindros went on to have a career cut short by injuries.

New York Rangers Trade of Rick Middleton for Ken Hodge

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    Rick Middleton was a young and talented scorer for the New York Rangers in the '70s who had the potential to be a real star in New York. 

    However, he was shipped out to the Boston Bruins for a player named Ken Hodge after two years in New York.

    Hodge went on to have one solid 62-point season on Broadway followed up by a lackluster 18-game 1977-78 campaign that ended his career.

    Middleton, on the other hand, scored 302 goals with the Bruins and had a decent career in which he tallied over 900 points. This trade was a huge bust for the Rangers and one of the worst one-for-one swaps in league history.

St.Louis "Blues" Jersey

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    This jersey features trumpets and blues notes to pay homage to the historic musical history associated with St. Louis. The jersey was so bad and was not approving to the St.Louis Blues staff.

    Mike Keenan refused to let his players wear it, and that is where this jersey died.

    However, history aside, nothing on this jersey had to do with NHL hockey and it is one of the worst jersey concepts in NHL history.

Los Angeles Kings Jersey

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    This Los Angeles jersey featured a king on the left chest side of the jersey. It was only in existence for one year and it isn't surprising considering the awful purple, black, gray and white color scheme.

    Not to mention, who doesn't think of cracking a Burger King joke when looking at this terrible hockey jersey?

Scott Gomez's Contract

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    Scott Gomez has one of the worst contracts in NHL history. He was given a seven-year, $51.5 million contract by Glen Sather and it was assumed to be a smart move at the time.

    However, when Gomez started to underperform, Sather was able to pawn him off to the Montreal Canadiens in exchange for future All-Star defender Ryan McDonagh.

    The picture basically sums up how the fans and how the Montreal Canadiens likely feel about Scott Gomez.

The Trapezoid

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    The trapezoid was implemented into the NHL after the 2004-05 lockout in an attempt to curb the goaltender's ability to play the puck.

    This rule really affected Martin Brodeur; he acted like a third defenseman for the New Jersey Devils because of his apt puck play ability.

    The trapezoid was a stupid addition to the NHL, and I wouldn't be shocked if it is phased out in the next few seasons.

Gary Bettman

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    Gary Bettman has been the NHL's commissioner since 1993 and under his watch there was the 1994-95 lockout, the 2004-05 lockout and the 2012-13 lockout.

    Bettman is a brilliant businessman with a law degree from Columbia University, but his rigidness when it comes to negotiating really has put the league and its players in awkward positions.

    It is completely asinine that after a year in which record-setting revenue was recorded, the league is heading to yet another work stoppage under Bettman's watch.

2012-13 Lockout

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    The NHL has had revenue grow exponentially over the past few seasons and 2011-12 was a record-setting year for the league.

    Despite the vast success of the sport, the billions of dollars in revenue that were generated and the appeal worldwide, the NHL and NHLPA could not iron out a collective bargaining agreement before the Sept. 15 deadline.

    With the two parties far apart on a few issues, it appears this lockout could last a while.

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