NHL history: Worst trade in each team’s history

NHL history: Worst trade in each team’s history: Anaheim Ducks

The Anaheim Ducks were trying to hold on to their glory days in 2009 when they traded away two young assets to bring Ryan Whitney into the fold. He came at a trade deadline deal with the Pittsburgh Penguins, who weirdly were trying to fighting for a Stanley Cup with Sidney Crosby and Evgeni Malkin directly in their primes.

They sent Chris Kunitz to the Penguins, who because one of the best wingers to play with Crosby. They had unreal chemistry, and it came immediately. He had 14 points in 24 playoff games as the Penguins became Stanley Cup Champions that very season.

Meanwhile, Whitney was fine in Anaheim, but he wasn’t anything to go home about. In the final 20 games of the 2008-09 season, Whitney scored exactly zero goals and had 10 assists. In the playoffs, he had six points in 13 games and the Ducks were out in the second round. Whitney wasn’t even close to as good as Kunitz in the deal that season, let alone for the next 10 seasons.

Whitney was traded the very next season to the Edmonton Oilers for Lubomir Visnovsky. They gave up a future four-time Stanley Cup Champion for someone who only spent 82 games with the franchise. This one hurt.

NHL history: Worst trade in each team’s history: Arizona Coyotes

It’s a tale as old as time. The Arizona/Pheonix Coyotes have traded away young players on the cusp of stardom only to see them become stars in other places. Or, they develop stars who then become too expensive, and they have to trade them away too. Although this could have easily been the Taylor Hall trade with the Devils, the fact they only ended up losing one 1st-round pick in the deal, and the Yotes made up with the lost picks with other trades puts the deal that lost Danny Briere as the worst trade in team history.

Chris Gratton was a mammoth forward who was going to bring some toughness to the Coyotes. He could also score, so it wasn’t the most egregious deal on paper. Briere was a smaller forward who might not have stayed in the NHL. Still, the fact that Yotes GM Michael Barnett ended up giving the Sabres a better pick with the better player is preposterous. Gratton spent a little over a season in Phoenix before he was traded to Colorado.

Meanwhile, Briere became the face of the franchise for Buffalo. After the trade, he only played for Buffalo for four years, but he had more than a point per game and really took them to places they hadn’t seen since. It came with two great playoff runs in 2006 and 2007 where the Sabres were actually considered a true contender.

The Sabres turned that draft pick into Andrej Sekera, who would go on to play seven years in Buffalo and 15 years overall in the NHL. The pick the Coyotes made was Liam Reddox, who played 100 games in the NHL and none of them were for the Coyotes.

NHL history: Worst trade in each team’s history: Boston Bruins

There was a spell in the early and mid-2000s where the Boston Bruins were making mistake after mistake. It seems like forever ago, but the Bruins were a laughing stock for a while. Then, they built the franchise that eventually won the 2011 Stanley Cup Championship. Before that, they made two of the most infamous trades of this era. One was sending Tyler Seguin to the Dallas Stars, but that didn’t have the long-term ramifications that sending Joe Thornton to the San Jose Sharks did.

Trading Joe Thornton when the Bruins didn’t think he was a fit is fine, but the return is awful. Wayne Primeau played 101 games in Boston as the veteran in the deal. Brad Stuart played 103 games in Boston. Marco Sturm had three fine seasons in Boston and then two miserable seasons. The Bruins traded a 26-year-old star for no pieces that could grow into something great. They wanted three NHL players, but they got three nickels for a dollar.

Thornton went on to have a future Hall of Fame career. He had north of 1,000 points in 15 seasons with the San Jose Sharks. He is still playing now, signing with the Toronto Maple Leafs this past season. The Bruins could have Thornton’s jersey going to the rafters, and who knows what the Bruins could have done with Thornton on some of those disappointing playoff teams. These two seem like they needed each other, but impatience led to a bad trade all around.

NHL history: Worst trade in each team’s history: Buffalo Sabres

The Buffalo Sabres really didn’t have a choice than to trade Dominik Hasek before the 2001-02 season, but they weren’t forced to make a bad trade. They really didn’t get a good return for one of the best goalies of all time, sending him to the Detroit Red Wings for Vyacheslav Kozlov.

Hasek easily went on to win the Stanley Cup with the Red Wings. He put up six shutouts in the playoff while playing behind the best defense of his career. He would win another Stanley Cup with the Red Wings during his 43-year-old season, and the Sabres were left with two assets.

Kozlov played one season in Buffalo before he was traded to the Atlanta Thrashers. The 1st-round pick was the last pick of the round. That pick eventually went to the Atlanta Thrashers, who took Jim Slater. He was a fine player but nothing great. This return is absolutely terrible. This was also a Sabres team that was building a young core that would lead them to a great stretch in the mid-2000s. Who knows, if the Sabres were able to get a better return in terms of young assets for Hasek, they might have gotten someone who could put them over the top in those 2006 and 2007 runs.

The Sabres traded away the best player to ever enter the Buffalo area. Yes, he is even better than Patrick Kane. They got basically no value for him. Hasek was definitely older, but teams would be willing to spend on someone who could win them the Stanley Cup.

NHL history: Worst trade in each team’s history: Calgary Flames

The Calgary Flames actually have a long history of pretty bad trades, but their best trade is still better than any of their bad trades adding Jarome Iginla. This trade always made absolutely zero sense. The Calgary Flames had a star defensemen in Dion Phaneuf who was only 24 years old.

This deal was huge, and it’s a lot of pieces to go through. Phaneuf was a 20-goal scorer from the blue line that looked like he could get better in his own end. He was a Calder Trophy finalist the same season that Sidney Crosby and Alex Ovechkin were rookies. The Maple Leafs were looking for a defenseman who could hold down the fort for the next decade. That’s why they pulled the trigger on this deal.

Rumors were surrounding the Flames that year, and locker room issues might have forced a trade, but Phaneuf was good in Toronto, so it was likely fixable whatever it was. They ended up getting a bevy of players instead of looking for picks and prospects.

The four players the Flames traded for were all older than Phaneuf, so this did nothing to help their struggling prospect pool. Matt Stajan was the major piece going the other way, and he was a good two-way player for the Flames. However, in his nine years in Calgary, he never scored more than 33 points in a season. The Flames had a really good piece, but because they didn’t have their house in order, they got a terrible trade.

NHL history: Worst trade in each team’s history: Carolina Hurricanes

This one goes back to the days of the Hartford Whalers. The Whalers were looking for a starting goalie, and the New Jersey Devils had Martin Brodeur ready to go. So, they sent their previous starter Sean Burke and young defenseman Eric Weinrich to the Whalers for young, hard-nosed center Bobby Holik and a couple of draft picks. Weinrich had a decent career playing for a total of 17 years in the league, but only two of those years came with the Whalers. Meanwhile, Burke was fine in Hartford and even started the franchise in Carolina, but he was eventually traded away as well.

Meanwhile, Bobby Holik was a huge part of the Devil’s first two Stanley Cups. He ended up playing the next 10 seasons in New Jersey, giving them one of the best examples of a 90s center. He could knock you out with his stick while also scoring 30 goals. There was something extra he brought to the lineup, and while he would come off like Tom Wilson in today’s NHL, he was beloved in his time with the Devils.

That 2nd-round pick probably doesn’t look too consequential until it comes out that the Devils got Jay Pandolfo with the pick. Pandolfo played 13 seasons with the Devils, helped them win two Stanley Cups, and he was an integral part of the team’s top-ranked penalty kill. This is two championship-caliber players for two players who had only a small impact on the overall franchise.

NHL history: Worst trade in each team’s history: Chicago Blackhawks

This guy? Again? Yeah, Dominik Hasek was a part of two of the worst trades in history, but this one is so much worse since the Chicago Blackhawks got none of the benefits from one of the best to ever put on the pads. Hasek was drafted in the 10th round by the Blackhawks, and they literally waited seven years for him to make the NHL only to trade him after 25 games.

For Hasek, the Blackhawks made themselves a part of one of the strangest trades in the history of the league. The Sabres traded Christian Ruuttu to the Winnipeg Jets for Stephane Beauregard. Then, they paired him with a 4th-round pick to get Hasek. Right after that trade, the Blackhawks traded Beauregard back to the Jets for, you guessed it, Christian Ruuttu.

Ruuttu played a total of 158 games for the Blackhawks before they traded him to Vancouver in the middle of the 1995 lockout-shortened season. It didn’t exactly move the needle. The Blackhawks had a prime Ed Belfour, so it’s not like they needed Hasek, but getting such a weak return for one of the best is inexcusable. Hasek went on to carry the Sabres for years, even taking them to the Stanley Cup Final (somewhere the Blackhawks never went with Belfour), and eventually won the Cup with the Red Wings.

NHL history: Worst trade in each team’s history: Colorado Avalanche

Sometimes a trade isn’t bad because of the return or what was given up, sometimes it’s bad because of what it saddles a team with for years. The Colorado Avalanche were looking to keep the dynasty going after Patrick Roy put his skates away for good. They looked to an old friend who gave them a goalie in the past.

Let’s start with the return. David Aebischer was nothing special. Getting Theodore in his prime for a young goalie who couldn’t handle the pressure of a starter was just fine. This was actually a great trade when it happened. The Avs couldn’t waste the time of Joe Sakic who quickly entered his late 30s and only had a few years of elite hockey left. The young Avs were starting to develop like Paul Statsny and vets like Milan Hejduk and Andrew Brunette were ready to step up.

Theodore gave them another star to push the Red Wings, Ducks, and Sharks in the Western Conference. He wasn’t very good in the first part of his career, putting up a .887 save percentage in 2006. Then in 2007, he lost his starting job to Peter Budaj. The Avs missed the playoffs, and they were never really Stanley Cup contenders again.

Theodore was good for the Avs in 2007-08, but he was swept out of the playoffs by the Red Wings in the second round. This wasted the last years of Sakic’s career, as he ended up retiring just one year later. Luckily, Sakic learned from this mistake and won’t be making another goalie mistake like he saw his predecessor make as the Avalanche GM.

NHL history: Worst trade in each team’s history: Columbus Blue Jackets

The Columbus Blue Jackets made the fatal mistake of thinking they were contenders when they weren’t. At the end of the 2010-11 season, they had made the playoffs once in the team’s 10 years history. Scott Howson was looking to accelerate the timeline for the Blue Jackets by trading for an available star. The issue is he trade for Jeff Carter, who could score a ton but wasn’t a franchise-changing player.

Carter spent one injury-riddle season with the Blue Jackets. That’s right, the Jackets sent a haul to the Flyers to get one bad season from their new “star”, before shipping him off to the Los Angeles Kings for Jack Johnson and what ended up being the last pick of the 1st round in the 2012 NHL Draft.

What did the Flyers get out of this deal? They got Jakub Voracek, who is a massive piece that led the Flyers into the next era. He scored north of 600 points in ten seasons with the Flyers. That alone makes this trade a massive win for the Flyers. Don’t worry, it gets worse.

The 1st-round pick the Flyers got in the deal was eighth overall, and the Flyers drafted Sean Couturier. He has 507 points in 575 games and is constantly a Selke Trophy candidate, winning it in 2020. These two players are what makes a winning franchise when stars are built around them. The Flyers have been contenders for the past decade in part because of this trade. If only they could have found the right goalie during this time, but we’ll get to that in a minute.

NHL history: Worst trade in each team’s history: Dallas Stars

Draft day trades don’t get much love on lists like this, but they deserve more flack. Draft trades could completely change a franchise forever. That’s what happened here, and it even created a rivalry between the Stars and Ducks. The 2003 NHL Draft was one of the greatest in history. 15 players played more than 1,000 games, and that doesn’t include the number-one overall pick, Marc-Andre Fleury.

This was a comedy of errors for the Stars. They traded the Ducks the 28th-overall pick for two 2nd-round picks. On paper, that should be a great trade. Getting value like that in the draft is awesome. Unfortunately, the Stars botched the picks. The Ducks, however, did not. They took Corey Perry just a few picks after taking Ryan Getzlaf. This completely changed the history of the Ducks, and they eventually won the 2007 Stanley Cup with the help of these two.

The Stars COULD have made this a good trade. With the 36th-overall pick, they could have taken Patrice Bergeron, Shea Weber, or Corey Crawford. Instead, they took Vojtech Polak. He played five NHL games. With the 54th-overall pick, they took B.J. Crombeen over David Backes. Think about this, the Stars could have had Loui Eriksson, Patrice Bergeron, and David Backes in the same round. That might be the best 2nd-round of all time.

Instead, they got five total games out of this trade while the Ducks got 988 games and an MVP season out of Perry.

NHL history: Worst trade in each team’s history: Detroit Red Wings

This is actually two terrible trades, both involving Hall of Famer Terry Sawchuk. The Red Wings overthought the process after winning four Stanley Cups in six seasons. They wanted to get younger, so they traded the best goalie in the world. Terry Sawchuk went to the Boston Bruins for a massive package of players. Unfortunately, none of the players worked out. So, the Red Wings were desperate to get their goalie back.

The Bruins wanted John Bucyk in the trade, and that was the right move by them. Bucyk went on to play 21 years with the Bruins, scoring 1,300 points in the process. He’s in the top 25 all-time in points scored. The Red Wings gave that away when the kid was still 21 years old.

But getting back a Hall of Famer is good, right? Well, the Red Wings never won another Stanley Cup Championship. They eventually sent Sawchuk to the Toronto Maple Leafs, where he was able to win his fifth Championship.

The Red Wings took decades to recover from this. They went from 1955 to 1996 without a championship. It’s hard to fathom now, but this made the Red Wings the league’s laughing stock. It’s hard to imagine after how good they were in the 90s and the first decade of the 2000s, but even when they were good, they weren’t a threat. It all started with trading away its franchise goalie and the desperate move to get him back.

NHL history: Worst trade in each team’s history: Edmonton Oilers

It’s the most infamous trade in the history of sports and it’s not because of how happy everyone was with the results. The Wayne Gretzky trade transcends hockey. It even transcends sports. Moms in mid-western Montana know about the Wayne Gretzky trade. Teens on the beach going through Tik Tok in Southern California know about the Wayne Gretzky trade. Your grandmother in South Florida knows about the Wayne Gretzky trade.

The Edmonton Oilers could have been the greatest dynasty in the history of sports by taking over the NHL for a decade, but the franchise needed money and the Los Angeles Kings had a lot of it. They had “The Great One”, but for the first time in eight years, he didn’t lead the league in points. He only scored *gasp* 149 points in 1987-88. The Oilers traded him that offseason in a deal that would shock the NHL landscape.

The Kings got a player that would revitalize hockey in LA. Gretzky was still great, leading the Kings to heights they never really saw on the ice. The town was so used to dominating on the basketball court that hockey was a nice surprise.

Meanwhile, the Oilers got two players and three draft picks along with cash. Martin Gelinas had a really good career, but he only played parts of six seasons with Edmonton. After a 100-point season in his first year in Edmonton, Jimmy Carson played five games the next season before he was traded to the Red Wings.

The trade tree is impossible to follow when it comes to the 1st-round picks. One was traded to the Devils. Another brought Martin Rucinsky who only played two games for the Oilers. The third pick took Nick Stajduhar, who played two games in his NHL career. It’s a bad trade even if it brought some really good pieces. Carson couldn’t handle the pressure of being the guy traded for Gretzky, and that probably derailed his career. The picks didn’t really work out, and Gretzky was still one of the best of all time for the next decade.

NHL history: Worst trade in each team’s history: Florida Panthers

We haven’t heard anyone suggesting that the Florida Panthers be moved to the first city that will have them in a long time. That’s because the team has been very good as of late. They made the playoffs this season with more points than the eventual Stanley Cup Champion Tampa Bay Lightning. They have stars in Aleksander Barkov and Jonathan Huberdeau, and the team looks to be on the up and up. This could have been their reality for years if they just held onto Roberto Luongo.

At first, it looked like the Canucks traded a lot to get Luongo. Todd Bertuzzi was a very popular player at one point, but an on-ice incident changed everything. We’ll get to that in a minute. Alex Auld was a promising goalie prospect, but he never really lived up to the expectation. Bryan Allen was fine.

Bertuzzi needed to leave Vancouver because the awful Steve Moore incident would always live over his head while he was there. It should have. He almost killed a guy on the ice. The Panthers signed up for that controversy, and Bertuzzi only ended up playing seven games for the Panthers because of injuries derailing his season.

Meanwhile, Luongo went on to become the best goalie in the league. He’s the best goalie in Canucks history, and it’s either him or Henrik Lundqvist as the best goalie of this era. They were great, and the Canucks didn’t really lose anything in the trade. It’s one thing to have a contract dispute with a player, but it’s another to get no draft picks in a deal and settle for depressed assets.

NHL history: Worst trade in each team’s history: Los Angeles Kings

The Kings learned well before the Gretzky trade what it was like to move a fan favorite way before he was ready to go. Butch Goring was trying to be part of the solution in LA. He didn’t want to leave. The Kings didn’t care, and they traded him to the New York Islanders for Dale Lewis and Bill Harris. Goring became a very important part of the Islanders dynasty.

Goring scored 19 points in his first playoff run with the Islanders, winning the first of four straight Stanley Cups. The next season, he scored 20 points in 18 games, winning the Conn Smythe in the process. He did fall off precipitously after his second season with the Islanders, but he was still a veteran presence on two Cup Final teams, and he even got some Conn Smythe votes in his fourth season for the team.

Meanwhile, the Kings got Dale Lewis, who played exactly zero games for the Kings. He only played eight games in the NHL. Billy Harris was a veteran in the deal, but he played just over 100 games before he was traded to Toronto. Los Angeles traded for him again to end his career, but that wasn’t a part of this trade.

The Kings traded a dynasty maker for basically nothing. There was nothing that really added to the value of the franchise. Goring pushed the Islanders to two of its four titles, and they might not have them without him.

NHL history: Worst trade in each team’s history: Minnesota Wild

This is another trade that looked great on paper. Honestly, the Minnesota Wild didn’t come out of this with no value. Brent Burns was not a very good winger with the Wild. The Sharks still tried to make him work on the right wing, but it never did. They moved him to defense permanently during the 2014-15 season, and he never looked back.

Burns quickly became one of the best offensive defensemen of this era. He scored between 60 and 80 points every season, and he won the Norris Trophy in 2017. The Sharks went into the next era with Burns at the forefront. He was the biggest star on the team despite having Joe Thornton still on the team, and everyone loved rooting for Burns.

Meanwhile, the Wild got Devin Setoguchi, who played just two seasons in Minnesota, and Charlie Coyle, who had a pretty good career before he was traded to the Boston Bruins. The 1st-round pick turned into Zack Phillips, who was never very good. They could have had Rikard Rickell, but that’s neither here nor there.

The Sharks did waste that 2nd-round pick on 23 games of Dominic Moore, but not every trade can be perfect. The Wild absolutely lost this trade, and Burns would have been a lot of fun. Obviously, there’s a huge asterisk here because the Wild may have never moved Burns to defense, so who knows what that future looks like. Still, the Sharks made the move and it changed their history.

NHL history: Worst trade in each team’s history: Montreal Canadiens

There are some trades on this list that are just plain easy. This is one of them. This might be the worst trade in NHL history. The Montreal Canadiens were forced to choose between their franchise goalie and their head coach. They picked the head coach, and after that coach left Patrick Roy in to allow nine goals against, embarrassing him in the process. Roy would never play another game for the Canadiens again, and the team eventually traded him to the Colorado Avalanche.

Montreal hasn’t won anything since that day. Roy was in the net for Canada’s last Stanley Cup win. He actually went on to win the Stanley Cup the season he was dealt. It was his first of two Cups in Colorado, as he also led the Avs to a championship in 2001.

Meanwhile, the Canadiens took what they could get. What they could get was not much. Andrei Kovalenko didn’t make it past this season with the Canadiens. He was on the Edmonton Oilers the next season. Martin Rucinsky played seven seasons with the Canadiens. He was a hard-nosed player who was in the penalty box a lot. It’s not exactly what you want for Patrick Roy. Jocelyn Thibault was the replacement in the net, and that just wasn’t fair to him. He was gone in a few years.

Oh, and on top of Roy, the Canadiens traded away their captain Mike Keane. This trade somehow gets worse! He brought a certain leadership quality that helped in the playoffs.

NHL history: Worst trade in each team’s history: Nashville Predators

This one might fall under the radar, but the second half of the Matt Duchene trade is just as bad as the first because of who the main piece of the deal became. The Colorado Avalanche got a legitimate top defenseman in Sam Girard as part of a bigger package for Kyle Turris, who was sent to them in the Matt Duchene trade with Ottawa.

The Avs probably have the best young defenders in the league with Girard, Bowen Byram, and Cale Makar leading the pack. Girard only played five games with the Predators before they shipped him out as a 19-year-old stud prospect. It’s already a terrible trade if it was Girard for Turris straight up. However, there’s more to it.

Vladislav Kamenev was a decent prospect, but he never really got a chance in Colorado and he left for the KHL. That was just a year ago, so the Avs will hold onto his rights for a while. If he decides to return to the NHL, the Avalanche would be able to either welcome him back or get something for him in a trade.

The 2nd-round pick ended up turning into a 3rd-round pick and a 5th-round pick after a trade down with Pittsburgh. It’s way too early to just those picks, as they take too much time to develop.

The Predators have a pretty good defense led by Roman Josi. It was even better when they made the trade because P.K. Subban was still there, but after trading him, Ryan Ellis going to the Flyers, and Mattias Ekholm could be the next guy gone via trade. Having Girard in this lineup would make these defensemen trades make sense, but the Preds seem like they could be sent into a rebuild because of this missing piece to the puzzle.

NHL history: Worst trade in each team’s history: New Jersey Devils

A former Norris Trophy winner still in his “prime” comes over to a team looking for an identity? Ray Shero had the right idea when he traded a few spare parts to the Nashville Predators for defensemen P.K. Subban. Admittedly, Subban gets more hate than he deserves from the Devils fanbase, but this trade had long-standing impacts beyond this specific trade.

Obviously, the Devils took on a $9 million salary to keep Subban. This impact the Taylor Hall negotiations and they couldn’t just throw a blank check his way. Maybe that’s a good thing in the long run, but they were forced to sell quicker than they thought possible. They eventually traded away Wayne Simmonds, Blake Coleman, Andy Greene, and Sami Vatanen before the trade deadline ended.

This, after the Devils fired head coach John Hynes and GM Ray Shero. The Subban deal went so terribly, that the Devils had to reset the entire franchise. If he was playing better then everything would still be in place right now. Shero would still have a job. Hynes probably isn’t in Nashville. The Devils are enjoying an $11 million Taylor Hall, and Jack Hughes probably doesn’t waste his first two years.

There are more repercussions to this trade. The Devils also wanted to trade for Nikita Gusev, but they didn’t have their 2020 2nd-round pick, so they had to trade their 2021 2nd-round pick to the Vegas Golden Knights. This meant they didn’t have a 2nd for two years in a row. That led to them reaching for Shakir Mukhamadullin in the 1st round of the 2020 NHL Draft, and reaching for Chase Stillman in the 2021 draft. Neither player was going to make it to the 3rd round, so the Devils had to overpay greatly with a 1st-round pick.

On top of all that, the Devils couldn’t get a different top-line defenseman until now. They just signed Dougie Hamilton as Subban is in the final year of his deal. For the first two years, that $9 million salary forced them to attempt to play him first-line minutes. He shouldn’t be there.

Subban is a fine player now, but he can only really play two roles after those back injuries. The Devils traded for a player who could not play the same after he got hurt.

NHL history: Worst trade in each team’s history: New York Islanders

There are so many trades to choose from in this era of New York Islanders hockey. Mike Milbury might be the worst GM in hockey history. His batting average is near Pittsburgh Pirates levels. They were always selling because they never wanted to spend money. Unfortunately for them, athletes like to get paid a lot of money. So, we can choose from such stars as Roberto Luongo, Zdeno Chara, the pick that turned into Jason Spezza, Todd Bertuzzi, and Chris Osgood. He even traded away Olli Jokinen after getting him in this deal.

The Islanders desperately needed a star, and Zigmund Palffy was quickly turning into one. He had three seasons where he was scoring between 85 and 90 points with the Islanders, but he was dealing with injuries in the 1998-99 season.

Palffy could have been incredible, but he fell by the wayside because of shoulder injuries limiting his ability. He was out of the NHL by the age of 33, but he still made a major impact on the Kings. He had 340 points over 311 games that spanned five seasons. He was the face of the Kings when they absolutely needed one. They also added a few other pieces to the deal.

Milbury was sitting on his pieces, and the Islanders spent years trying to wash off the stink he left on Long Island. The team is in better shape now, but it took about a decade to recover from the Milbury era.

NHL history: Worst trade in each team’s history: New York Rangers

You can’t blame the New York Rangers for trying. They seem like they are always trying. Whether it’s making the major splash in free agency like they’ve done dozens of times, or making the major trade to bring the big name to Broadway, the Rangers are willing to make the move. Here, the Rangers took on a star who was past his prime and let go of a star that was not.

The Rangers were looking to change the culture after another embarrassing playoff defeat. They called their arch-rivals in Boston and asked for the team’s biggest name. They wanted Phil Esposito.

The price was heavy. Brad Park was already a five-time All-Star who had a ton left in the tank. He was great for Boston and even put up an epic performance in the 1978 playoffs (20 points in 15 games). The Bruins didn’t lose a star without getting one in return. That wasn’t the only thing they got. Jean Ratelle had a nice final six years of his career in Boston before retiring.

Meanwhile, Phil Esposito was still really good, but the Rangers were not. The “change of culture”  ended up changing the Rangers’ winning ways entirely. They missed the playoffs the next two seasons, and they lost in the first round in the season after that. They did make a run in 1979 and Esposito was great that season, but losing two really good players for a team that ended up needing a complete reset was bad for the Rangers.

NHL history: Worst trade in each team’s history: Ottawa Senators

This is the second time this one trade came on this list. It shows how bad the Colorado Avalanche swindled these two teams. The Ottawa Senators thought they were a legitimate Stanley Cup contender. They came close the year before, so they needed a center to push them over the top. They send the Avalanche, who were in a terrible rebuild at the time, Andrew Hammond, Kyle Turris, former 1st-round pick Shane Bowers, a conditional 1st-round pick, and another 3rd-round pick. The Senators could choose between the 2018 or 2019 1st-round pick. The Senators kept their 2018 pick to take Brady Tkachuk.

This had such long-standing implications on the Senators that they are still feeling today. The Sens immediately went into the tank. That season, the Senators went 28-43-11 and missed the playoffs. That’s why they kept the 2018 pick because they thought they’d be better the next season. Actually, they were even worse. They were one of the worst teams in the league, and they were a candidate for the number-one overall pick. The Avs ended up getting the fourth-overall pick and they took stud defenseman, Bowen Byram.

Turris turned into Sam Girard, so the Avalanche got two stud defensemen, Shane Bowers is a player who can still be good if given the chance, and they are now in Stanley Cup contention while the Senators are in year three of a massive rebuild.

NHL history: Worst trade in each team’s history: Philadelphia Flyers

The Philadelphia Flyers have been looking for a goalie since Ron Hextall left. They tried Ilya Bryzgalov, Brian Elliott, Steve Mason, Ray Emery, Martin Byron, and John Vanbiesbrouck as their starter over the past two decades plus. None has really worked out, and it’s really hampered them in the playoffs. The Flyers have had incredible players at forward and defense, but the goaltender position has always been a problem. Even now with Carter Hart in net, the Flyers still have questions.

It turns out they always had one of the best goalies in the league on the roster. Unfortunately for them, they traded him to the Columbus Blue Jackets.

Columbus never really found its way as a competitive team until Sergei Bobrovsky took over the net. The Flyers took a bunch of picks, none of which was a 1st rounder, to send Bobrovsky down the Pennsylvania Turnpike and over to Ohio. In seven years with Columbus, he only had a negative goal against above-average once, and he won two Vezina Trophies for some dominant performances.

Meanwhile, the Flyers have been looking for the stability they had. Mason came over from the Blue Jackets and he was considered the better prospect. That’s laughable now as Mason’s career quickly flamed out with the Flyers. Hopefully, Hart can bounce back and finally end the Flyers’ woes. This trade will continue to haunt the Flyers for wasting the prime of Claude Giroux and the rest of those really good Flyers teams.

NHL history: Worst trade in each team’s history: Pittsburgh Penguins

This seem like a fine enough move when it happened. The Pittsburgh Penguins had Matt Murray and Marc-Andre Fleury. Fleury had a couple of below-average seasons under his belt, and Murray just helped them win back-to-back Stanley Cups. It was a really good time to be a Penguins fan, and losing Fleury was a necessary evil.

Looking now, just four years later, and it was probably the worst possible move the Penguins could make. Sidney Crosby and Evgeni Malkin are now in their mid-30s, and the goalie position is a major flaw. Murray ended up turning into a pumpkin and they traded him to the Ottawa Senators. Tristan Jarry looked like he could be the future, but he was not very good last season. Now, Penguins fans want Fleury back desperately.

Not only did the Penguins give Fleury away, but they gave away a 2nd-round pick in the very good 2020 NHL Draft. This is just to get Fleury off the roster. The Golden Knights were going to take Fleury. He was going to be the face of their franchise. Yet, George McPhee was able to get the Penguins to just throw in a 2nd-round pick.

The Knights eventually used that pick to get Robin Lehner, giving them two goalies for the price the Penguins paid to get rid of one. Meanwhile, the Pens are wasting the last good years of the Malkin-Crosby partnership and they still have cap problems. This “trade” was just terrible.

NHL history: Worst trade in each team’s history: San Jose Sharks

It takes a lot to trade away the face of the franchise. For the franchise in a small city like San Jose, it seems to mean more. Think about Jarome Iginla in Calgary, Rick Nash in Columbus, and Daniel Alfredsson in Ottawa. There is more pressure on these players to stick around so the fans have something to root for. Owen Nolan was that for the Sharks, as he was the team’s best player and its captain. The Toronto Maple Leafs came calling near the trade deadline in 2003, and the Sharks made the move.

Alyn McCauley was fine in his time in San Jose. He had 47 points n 2003-04 and came in third for the Selke Trophy. He was never as good after the NHL Lockout, so the wheels came off pretty quickly. The Sharks obviously hoped he worked out more than a season and a half, but that’s the risk with the impending lockout.

Brad Boyes played one game with the Sharks before he was traded to the Boston Bruins. He had a decent career, but the Sharks got none of it.

The 1st-round pick came in the 2003 NHL Draft, one of the best drafts of all time. This pick made this deal worth it. That is until the Sharks actually made the pick. The pick was 21st, but the Sharks traded up to 16 to take Steve Bernier. The very next pick was Zach Parise. Two picks after that were Ryan Getzlaf, and future Sharks’ great Brent Burns went 20th. If they just kept the 21st pick, they could have taken Corey Perry, Ryan Kesler, Patrice Bergeron, Shea Weber, or Corey Crawford. The Sharks ended up with nothing from trading for their captain just a few years later.

NHL history: Worst trade in each team’s history: St. Louis Blues

The St. Louis Blues made one of the best trades in franchise history when they traded Brendan Shanahan for Chris Pronger. It saved them from one of their worst moves when they signed Shanahan to a restricted free agent contract. They ended up losing Hall of Fame defenseman Scott Stevens in compensation to the New Jersey Devils, so Shanahan came at a hefty price. So, just a few years later, the Blues flipped him for what would become one of the best defensemen in the league.

The Stevens deal technically wasn’t a trade so it doesn’t qualify, but trading away Pronger in his prime definitely qualifies. Teams were in flux after the implementation of the salary cap after the 2004 NHL Lockout, and Pronger was a player that teams couldn’t seem to handle. He was traded three times over the next five years.

This trade really hurt, though. Pronger had spent a decade in St. Louis, and he was bringing the team to heights that seemed like they were only beginning. They made the playoffs every season with Pronger. The season they traded him, they missed the postseason for the first time since 1979. The Blues were wildly consistent even if they were never truly Stanley Cup contenders.

Trading Pronger sent the Blues into a tailspin. The return was atrocious. Eric Brewer only had 95 points in 335 games with the Blues. Doug Lynch never played another game in the NHL. Jeff Woywitka was never an NHL regular and played as a 13th forward for most of his career. This is what the Blues got for one of the best defensemen of this era. The Oilers took Pronger and went to the Stanley Cup Final before immediately trading him again.

NHL history: Worst trade in each team’s history: Tampa Bay Lightning

The Tampa Bay Lightning had a great early era led by Martin St. Louis, Vinny Lecavelier, and Brad Richards. For six and a half seasons, they were contending in the Eastern Conference, and they had to keep teams on their toes because they could strike at any point in the game. Richards led the Lightning to the 2004 Stanley Cup and won the Conn Smythe along the way. He had seven game-winning goals in that postseason alone.

The Lightning ended their franchise’s best days (well, before this current run) a little prematurely to deal with the salary cap. The Lightning were never the same, but Richards still had a lot left in the tank. He had a couple of good seasons with Dallas before signing a huge contract with the New York Rangers. That didn’t exactly work out, but the Lightning could have had this great core together for another few years.

The Lightning got some good players in return, but they didn’t get the best results from them. Jussi Jokinen had a really good career, but he only lasted 66 games with Tampa. Mike Smith is still playing well today for the Oilers, but for three out of his four seasons in Tampa, his save percentage was .900 or less. Jeff Halpern was okay before he was traded to the Los Angeles Kings.

This could have been the trade to revamp the Lightning, but the team just couldn’t get it together. They eventually traded away St. Louis and bought out Lecavalier. It was a bittersweet end to a great run in Florida.

NHL history: Worst trade in each team’s history: Toronto Maple Leafs

This one will never not hurt Maple Leafs’ fans. Back in 1989, the Toronto Maple Leafs thought they were contenders who just needed another piece. Tom Kurvers was a decent defender who was in the prime of his career. The Leafs called the Devils and offered the team’s 1st-round pick to get him. However, it wasn’t that season’s 1st-round pick, it was the 1st-round pick in the all-important 1991 NHL Draft.

Eric Lindros was the prize of that draft, as some said he was the best prospect to come out since Mario Lemieux. The Leafs didn’t think that would come up, but it did. The Leafs were absolutely terrible in 1990-91. They were actually a candidate for the worst record in the league, which would hand Lindros to the Devils on a silver platter. They had to actually make a trade with the Quebec Nordiques to make them worse and secure their spot at the bottom of the standings.

The Devils still ended up getting the third-overall pick from the Leafs, and they used it to take defenseman Scott Niedermayer.

All he did was lift the Devils to dynasty status alongside Scott Stevens and Ken Daneyko. Niedermayer became one of the best offensive defensemen in the history of hockey. He moved the puck better than any defenseman. The Leafs lost that for 89 games of Kurvers. He did score 55 points in those 89 games, but the Leafs never went anywhere.

NHL history: Worst trade in each team’s history: Vancouver Canucks

How does a trade back in 1985 lead to the Boston Bruins draft Milan Lucic two decades later? This one really hurt the Canucks, but the trade tree is absolutely fascinating. The Bruins got a magnificent player in Cam Neely, who played 10 seasons in Boston and even added two 50-goal seasons. Neely alone for Barry Pederson would have been a bad trade.

Pederson had a fine first two years in Vancouver, but he fell off a cliff in his 28-year-old season and the Canucks eventually traded him. The year the Canucks traded him to the Kings, Neely had a career-high 92 points.

The Bruins took Glen Wesley with the 1st-round pick in the trade. He would play seven years with the Bruins before they traded him to the Hartford Whalers for three 1st-round picks. It was a massive deal that would pay dividends to the Bruins for decades. They traded two of the players selected with those 1st-round picks for other 1st-round picks. They also got a 2nd-round pick for Sergei Samsonov which was eventually used to take Milan Lucic.

So, just a quick look at all the trades, the Bruins have had Lucic, Neely, Martin Jones, Collin Miller, Sean Kuraly, Trent Frederic, Jakub Zboril, Nathan Hornton, and Gregory Campbell all for Barry Pederson. Maybe if the Canucks just kept their assets, they could have changed fortunes. Instead, Neely watched from the front office while the Bruins took the Canucks best shot at the Stanley Cup away from them.

NHL history: Worst trade in each team’s history: Vegas Golden Knights

This one literally just happened. Marc-Andre Fleury might retire and it might be a null move, but the long-term impacts of this trade will be felt beyond what happens on the ice. Before this trade. Vegas was a destination for players. The city is a ton of fun, the fans are some of the best in the NHL, the building is always full, the owners are committed to winning, and they have a good core to build around. However, they went about the past few offseasons in such a terrible way, and now, the shine on the Golden Knights has worn off.

This was when things hit a fever pitch for the Knights. Fleury told the Knights he didn’t want to be traded, but they asked him to give them a 10-team no-trade list anyway. When the Blackhawks weren’t on it, they dumped him for nothing. There was a prospect in the trade, but he could still play for the Blackhawks in a strange situation not worth getting into.

The Knights tried to dump the cap of the reigning Vezina Trophy winner. That’s right, Fleury just won the trophy as the best goalie in the NHL, and he ended up being a salary cap dump. That’s not even the worst part. The Knights didn’t even discuss the trade with Fleury before making the trade call, the information got leaked to the media, and Fleury learned about his trade on Twitter. That’s the worst.

After how the Knights have treated other players in the past like Nate Schmidt and Tomas Tatar, it doesn’t help them when trying to bring other stars to Nevada. They have to treat players better. That doesn’t mean not trading them, but it’s all about how you go about the trade. Give your player a heads up, and don’t hide behind the trade call before making the player call.

NHL history: Worst trade in each team’s history: Washington Capitals

There aren’t many trades on this list that are absolutely obvious to everyone, but this one definitely is. The Washington Capitals wanted to add pieces to make a run to the playoffs in the lockout-shortened 2013 season. They were sitting at hockey .500, so the Capitals needed to make a move so they didn’t waste another year of Alexander Ovechkin’s prime. So they paid a hefty price to get Martin Erat from the Nashville Predators.

It worked. The Capitals made the playoffs just like they wanted. They lost in the first round to the New York Rangers, but they made the playoffs. So that counts for something, right?

Well, they lost Filip Forsberg in the deal. He was the 11th-overall pick in the 2011 NHL Draft, so it’s not like they didn’t know he was going to be good. They took one of the highest picks of the era on Forsberg. They just sent him away for three playoff wins and another Game 7 disappointment.

Forsberg has turned into a star with the Predators. He’s still well into his prime, turning 27 years old right before next season. He already had two 30-goal seasons under his belt, and he would look really good next to Ovechkin in the latter years of his career. Instead, he will continue with the Preds unless they get a massive trade offer this offseason.

NHL history: Worst trade in each team’s history: Winnipeg Jets

Yes, this is the original iteration of the Winnipeg Jets that eventually turned into the Arizona Coyotes, but this trade is so bad that it sent ripples for decades.

Teemu Selanne was a superstar for the Jets. He had a 76-goal season under his belt in his rookie season. When he was traded in the middle of the 1995-96 season, he already had 24 goals in 54 games. Right after the trade, he went off for 16 goals in the season’s final 28 games for the Mighty Ducks of Anaheim.

The Jets were trying to build a team that was cheaper before the move to Arizona. So, they trade Selanne along with Marc Chouinard for Chad Kilger, Oleg Tverdovsky, and turning their 4th-round pick into a 3rd-round pick.

Kilger was traded less than a month later to the Chicago Blackhawks. Oleg Tverdovsky had a few good seasons with the Coyotes, but he eventually returned to the Ducks. The Yotes traded him there for Travis Green and a 1999 1st-round pick.

Selanne went on to have a Hall of Fame career. Who knows what his future would have looked like if he moved with the Jets to Arizona, but it was clear Selanne had more in the tank than he was showing in Winnipeg. Something was off, and it went a lot better in Southern California. It’s still a terrible trade for the Jets. They didn’t get much at all in the deal, and they eventually traded both pieces away, one in an almost immediate fashion.