NHL history: Best trade in each team’s history

NHL history: Best trade in Anaheim Ducks history

The Anaheim Ducks had two really great runs in their history. In 2003, they went to the Stanley Cup Final mostly on the backs of Paul Kariya and Jean-Sebastien Giguere. Something was missing, though. The player most attributed with this franchise. Teemu Selanne came to the Ducks in a trade with the original version of the Winnipeg Jets. Selanne was already a star, but Winnipeg was about to move to Arizona and they could use a pool of prospects to build around.

The Ducks called the Jets new owners Richard Burke and Steven Gluckstern wanted to keep Selanne, but it became clear that the team was going to move him one way or another. So, when the Ducks called, the talks never really stopped. They talked through the GM meetings in Tuscon. Eventually, a deal got done.

The Ducks won this trade in spades. Oleg Tverdovsky was a decent player for Winnipeg and Arizona, but he was a role player at best. The 3rd-round draft pick turned into Per-Anton Lundstrom, who never played in the NHL.

Meanwhile, Selanne would play 966 games with the Ducks. He scored 988 points and helped the Ducks win the 2007 Stanley Cup in his second stint with the Ducks. He became a franchise legend and a Hall of Famer because of his time in Anaheim.

NHL history: Best trade in Arizona Coyotes History

There’s really only one deal here. The Arizona Coyotes have made a lot of trades in team history, but nothing made the impact that Jeremy Roenick going to the desert did. Roenick, like many stars who were traded in their prime, was once again having acrimonious trade talks with the Chicago Blackhawks, and instead of overpaying their star, the Blackhawks traded him.

The Blackhawks accepted Alexei Zhamnov, Craig Mills, and a 1997 1st-round pick to get Roenick. Zhamnov was pretty good with the Blackhawks. He played eight years in the Windy City and scored more than 400 points. Mills was not really an NHL player and spent most of his career in the minor leagues and finished up in Europe. The 1st-round pick turned into Ty Jones, and he was a major bust for the Blackhawks. He only played eight NHL games while with the Blackhawks and never really made an impact in the league.

Meanwhile, Roenick was a star for Phoenix when they were desperate for a star. They needed someone to get fans in the building when the team first moved from Winnipeg. As we said before, they just traded Teemu Selanne, so they needed another star to make up for it. Roenick could not score like Selanne, but his gritty style of play and ability to put up points gave the Coyotes exactly what they need.

NHL history: Best trade in Boston Bruins history

This one takes a trip into the time machine. Most of us weren’t alive in 1979, but everyone knows the stories career of Ray Bourque. The defenseman spent all but one full year of his career in Boston, but it was almost a career that happened in Los Angeles. Let’s explain.

Rogie Vachon left the Kings in 1978, and LA needed someone in net to help them into their next era. So, they called the Boston Bruins. Ron Grahame seemed like a good option since Boston still had Gerry Cheevers  on the roster. The Kings traded their 1st-round pick for Grahame, and everyone walked away happy. Well, that 1st-round pick ended up turning into Hall of Fame defenseman Ray Bourque.

There are other great trades in Boston history. They turned an aging Phil Esposito for Brad Park, who was their next great player. They originally got Esposito from the Chicago Blackhawks for a package of players. Tuukka Rask came from the Toronto Maple Leafs in exchange for Andrew Raycroft. One could easily argue that tops this list.

Nothing had the impact on this Bruins franchise that Bourque had. He played 21 seasons with the Bruins, scored north of 1,100 points in more than 1,500 games. There are few defensemen in the history of the league that have the resumé that equals Bourque. The Kings handed this great career to the Bruins on a silver platter. Meanwhile, Grahame lasted just over two seasons in LA before he was traded to Quebec and retired eight games later.

NHL history: Best trade in Buffalo Sabres history

This one HAS to hurt Chicago Blackhawks fans. The Blackhawks drafted Dominik Hasek with the 199th-overall pick in the 1983 NHL Draft. They waited seven years for him to make his NHL debut, and he made it 25 games in his career before the Blackhawks traded him to the Buffalo Sabres for Stephane Beauregard, a fellow goalie, and a 4th-round pick. We’ll start with the return for Chicago. Beauregard was traded THREE DAYS LATER. They sent him to Winnipeg for Christian Ruuttu. He played 158 games in Chicago before they traded him, too. The 4th-round pick turned into Eric Daze. He had a pretty good career playing 600 games and coming just short of 400 points.

The return in that trade for the Sabres was the greatest player in franchise history and possibly the best goalie of all time. Dominik Hasek was so much better than his peers, he was able to bring much worse teams much further in the postseason.

Hasek spent nine seasons in Buffalo. He led the league in save percentage six times. He won all of his record six Vezina Trophies in Buffalo. Hasek won those Vezina Trophies at a time when Patrick Roy and Martin Brodeur were also dominant in the league. That’s how good he was.

Hasek carried the Sabres to the 1999 Stanley Cup Final all by himself. Say what you want, he did that alone. This is the huge piece that Buffalo got for the price of a flier 4th-round pick and a goalie that was traded again days later.

NHL history: Best trade in Calgary Flames history

Sure, this trade really worked out for everyone involved because Joe Nieuwendyk continued his Hall of Fame career in Dallas and helped them win the 1999 Stanley Cup. Despite all that, there is no way the Stars don’t regret this deal, right?

Jarome Iginla became one of the best players in the NHL. He carried Calgary for years, and even brought them to the 2004 Stanley Cup Final. The team around him was quite awful, but he was still putting up between 70 and 90 points every season. Iginla was everything to this franchise, and he was just desperate for the front office to put something around him.

Iginla spent 16 years with the Flames and came in just under 1,100 points before he was traded to the Pittsburgh Penguins. This franchise is still considered Iginla’s franchise to this day. The Flames won the 1989 Stanley Cup, but more people associate this franchise with its biggest star than they do with that team.

Corey Millen finished off his career in Calgary, and it was fine, but Iginla was just so good for Calgary he might have kept them in Western Canada. Who knows. The team was so mismanaged outside of this trade that he was lifting them up higher than they deserved for a long time.

NHL history: Best trade in Carolina Hurricanes history

There are a lot of very interesting trades in the history of the Hurricanes franchise. Going back to the Hartford Whalers days, they traded Sylvain Turgeon for Pat Verbeek, who went on to have a great career in Connecticut. They started the career of “Mr. Game 7” Justin Williams when they traded Danny Markov to the Philadelphia Flyers. However, nothing had the impact on this franchise than the moment they traded for the man they now call “coach” Rod Brind’Amour.

Brind’Amour had an interesting career up to the point he came to the Hurricanes. He started his career in St. Louis. They tried to send him to New Jersey to get Brendan Shanahan. Instead, he was eventually traded to Philadelphia where he would spend the next nine seasons. Then, the Flyers made a crucial mistake, trading Brind’Amour in a superstar deal to get Keith Primeau. Except, Primeau had just a few seasons left in the tank. He was refusing to play for the Hurricanes without a new contract, and Brind’Amour would go to play for another decade after the deal.

Brind’Amour made an immediate impact on the Canes. His first full season with Carolina, he played a great two-way game and helped lead the team back to the postseason. Brind’Amour’s resumé speaks for itself. He scored 473 points in those ten seasons. He scored 18 points in the iconic 2006 run to the Stanley Cup. The NHL voted him as the Selke Trophy winner two-straight seasons. He always seemed to be in the right place at the right time. His clutch goals were the stuff of legend. Thanks to the Flyers looking to get themselves a star, they lost the type of player that helps teams win in the NHL.

NHL history: Best trade in Chicago Blackhawks history

We are going WAY back for this one. The Chicago Blackhawks have been on the other side of some really, really bad trades in team history. This one absolutely went their way. In fact, the Red Wings of this era were like the Peter Chiarelli of this era. They traded away Johnny Bucyk, Terry Sawchuk, and here trading Glenn Hall. The time after the Red Wings 1950s dynasty was not a good one.

Hall played ten years with the Blackhawks. In five of those seasons, the Hawks literally didn’t need a backup goalie because he played all 70 games. Another season he led the league with 64 games played. Not only was he a work horse, but he was efficient. He led the league in goals saved above average three times, he led the NHL in goalie point share five times in his ten seasons, and he helped the Blackhawks win the 1961 Stanley Cup.

The Red Wings didn’t get much back in return for Hall. Johnny Wilson and Forbes Kennedy played small roles immediately after the trade, but their impact was fleeting. Bill Preston never played for the Red Wings, and Hank Bassen wasn’t really a priority with Sawchuk playing for the team at the time.

This is actually all Ted Lindsey’s fault. He tried to unionize the Red Wings, and that angered the Wings owners. They traded him to the Blackhawks to get him away from getting the team rights in negotiations. He wasn’t a huge impact on the Blackhawks, but he did score 58 points in his second year in Chicago.

NHL history: Best trade in Colorado Avalanche history

The trade of Eric Lindross is going to be on most people’s lists because it helped the Avs build a dynasty. It brought them Peter Forsberg and a whole lot more. However, that happened during the Quebec years, so this opted for a trade that happened during the years in Colorado (even though the other trade had a real impact on the Avs).

Just a few years ago, the Avalanche were one of the worst teams in the league. They were forced to trade away names like Ryan O’Reilly, Jarome Iginla, and here they traded young center Matt Duchene for a massive package. This is the only three-team trade on the list, as it took a very complicated set of circumstances to make happen.

Duchene went to the Senators and struggled. They eventually traded him to the Columbus Blue Jackets after just over a season with the team. He never started and ended a season with the Sens.

For that, the Senators traded Colorado Kyle Turris, Shane Bowers, a 1st-round pick, and a 3rd-round pick. Bowers is on the cusp of finally making the Avalanche roster, and he spent most of last season on the taxi squad. They ended up taking Bowen Byram with the Senators 1st-round pick, which ended up being the fourth-overall pick. He’s going to be a star on the blueline along with Cale Makar and Sam Girard.

Oh, speaking of Girard, he came to the Avalanche in a second deal involving Kyle Turris going to the Nashville Predators. That also brought the Avs a 2nd-round pick (Filip Hållander) and Vladislav Kamenev. So, the Avs basically got a decades worth of a top-line defense on almost every team, plus a few extra pieces for a player that spent zero full seasons in Ottawa. Yeah, this is the best trade.

NHL history: Best trade in Columbus Blue Jackets history

The Columbus Blue Jackets had a really hard time making headway in the NHL over its first decade. The Rick Nash era never really put out anything of note before a really exciting player to not make the playoffs with. Things didn’t actually turn around until June 22, 2012, more than a decade after they joined the NHL in the year 2000.

The Philadelphia Flyers had a goalie issue since Ron Hextall retired. For the 13 seasons after Hextall left the Flyers, they had eight different starting goalies. One of them was Sergei Bobrovsky, but after they signed Ilya Bryzgalov, a 23-year-old Bobrovsky didn’t seem necessary. So, they traded him to the Blue Jackets, a team with a sad history, for some draft picks.

Bobrovsky almost immediately became one of the best goalies in the league. He posted a .932 save percentage in his first season in Columbus, he kept it over .920 four times over the next seven seasons, he won two Vezina Trophies while in Ohio, and he led the Blue Jackets to four times and even beat the President Trophy winning Tampa Bay Lightning in 2019.

Meanwhile, the Flyers got Anthony Stolarz, Justin Auger,and Taylor Leier for Bobrovsky. We have seen some bad goalie trades in the past, but this one might take the cake. Bobrovsky literally turned the franchise around in Columbus. His arrival sparked the next era and brought them out of “laughing stock” status.

NHL history: Best trade in Dallas Stars history

The Joe Nieuwendyk deal comes up a lot when discussing the best Dallas Stars deals of all time, but a lot of that has to deal with people being out on Tyler Seguin right this second. Seguin is still a very good player now, and he was a superstar for most of his career with Dallas. The deal the Bruins got in return for the former number-two overall pick was not good in the least bit.

The main piece they got back was Loui Eriksson. He played three seasons in Boston and scored 147 points. It appears the Bruins were getting a rapidly declining player, and they knew that when they let him sign in Vancouver. Joe Morrow was a former 1st-round pick, but he also only lasted three seasons in Boston. Reilly Smith was the best player to go to Boston in the trade, and the Bruins traded him two years later to get Jimmy Hayes (another really bad trade).

With the Stars, Seguin has been in Dallas for eight years, and he has 516 points. He was part of the team that went to the Cup Final in the bubble, with 13 points in 26 games. It wasn’t his best performance, but he was along for the ride. Meanwhile, Rich Peverley was decent in his one season in Dallas, but he had to retired after a medical condition on the bench.

Seguin is having a rough two years, but he is only 29 years old still. He can still be a prime superstar for the next five years. He missed most of this season, but he could be ready to dominate again next season. The Bruins have a whole lot of nothing to show for that trade.

NHL history: Best trade in Detroit Red Wings history

There are so many great Detroit Red Wings trades. They got Chris Chelios for two late 1st-round picks. The Brendan Shanahan deal was actually pretty even for both sides (the Whalers got Keith Primeau, Paul Coffey, and a 1st-round pick). However, getting Kris Draper from the Winnipeg Jets for literally $1 breaks the bank.

Draper was really good for the Red Wings for a really long time. He was a part of the Red Wings four Stanley Cup Championships from 1997 to 2008. He didn’t score a lot of points, but he did just about everything else really well. He would kill penalties, block shots, and get into passing lanes. The Red Wings knew how important that was from someone on the bottom six, and they didn’t let him go anywhere.

Draper won faceoffs, he stole the puck from the other team, he was someone who got possession when the Red Wings needed it. He knew who the stars were, so he used his effort in the defensive zone getting under other players’ skin or by tiring out players in the offensive zone. He was the ultimate decoy on offense, and it led to Cup runs many, many times. He doesn’t deserve the same respect as Chris Osgood, Shanahan, Steve Yzerman, or Niklas Lidstrom, but Draper ends up being the “final piece” for teams before they win the Cup.

He is now a fan favorite that lives on in Detroit history. They got all this for one American dollar. And this was 1993, so the Red Wings couldn’t just Venmo the Jets a dollar. They had to make an actual effort to send them the cash.

NHL history: Best trade in Edmonton Oilers history

There are a lot of bad Edmonton Oilers trades in the past. The Gretzky trade is probably the most famous trade in the history of the league. One literally just happened with Duncan Keith going to Edmonton on a deal that still pays him north of $5 million on the salary cap. However, the history of the Oilers has some really good trades.

Doug Weight is one that stands out above the rest. After the dynasty years of the 1980s, the Oilers went to playing spoiler in the 90s. Often, they took down the power houses of the Western Conference. That was on the backs of their star Doug Weight.

The Rangers traded Weight to the Oilers at the 1993 trade deadline for Esa Tikkanen. We’ll get to Tikkanen in a second, but Weight went on to play nine years in Edmonton. He was only 22 years old when he was traded, so the Oilers got his entire prime. He scored just under a point per game in his time in Western Canada (577 points in 588 games), and he was just as good in the postseason.

Meanwhile, Tikkanen played parts of two seasons (before a second two-year stint later in his career). He scored 54 points then left for St. Louis. He was on that Rangers championship team in 1994 and put up eight points in 23 games. Maybe those eight playoff points were worth the loss of a franchise legend for the Rangers, but this will always be a superstar trade for the Oilers.

NHL history: Best trade in Florida Panthers history

Finding a great trade for the Florida Panthers is hard. They don’t have a lot of great seasons in their history, and they were always trying to get the big fish. They did trade for Pavel Bure, and that was fun for a few years. He did have two 50-goal seasons in South Florida. However, the best run of the Panthers era might not have happened without Ray Sheppard.

The deal doesn’t get a lot of love, but it deserves more than it gets. Sheppard was traded to the Panthers near the trade deadline in 1996 as the Panthers were looking to make the playoffs. They sent a 2nd and 4th-round pick to the San Jose Sharks for Ray Sheppard. He only played parts of four seasons in Florida and scored 121 points. That’s not a superstar by any means, but what happens in the playoffs is well worth the price of admission.

Sheppard scored 16 points in 21 games as the Panthers upset the top-seeded Flyers and second-seeded Penguins on their way to their first (and only) Stanley Cup Final appearance. He was phenomenal in the first round series against the Boston Bruins, scoring eight points in the series.

Without Sheppard, the Panthers probably don’t make it past Boston. That means the Year of the Rat in the NHL Playoffs never happens. This run was too important to this franchise for it to not be in every fabric of “best ever” lists.

NHL history: Best trade in Los Angeles Kings history

Duh. This is all the analysis you need. The Los Angeles Kings got Wayne Gretzky from the Edmonton Oilers, then they talked them into GIVING UP MORE NHL ASSETS ON TOP OF IT. Sorry for yelling, but this trade is the subject of documentaries, books, road trip stories, and every other form of storytelling. This trade will live on in history.

Honestly, when we talk about possible trades for the best players in the NHL today, when one person calls the idea crazy, they bring up the fact that Wayne Gretzky was traded. And the Oilers made that trade. The Kings didn’t win the Stanley Cups the Oilers did with Gretzky, but they got a really good player for longer than people remember. Gretzky played eight seasons with the Kings, which is one less than the Oilers. He was injured for some of those seasons, so he “only” scored 918 points in 539 games.

Gretzky brought excitement to Los Angeles hockey. It was the one thing that could help any team compete with the Lakers in the NBA. The heights of his time with the Kings was upsetting those very same Oilers in the playoffs, then the next season they upset the defending champion Flames in the first round again. Then, three years later, Gretzky literally led the Kings to the Stanley Cup Final. High stick to Doug Gilmore aside, he scored the overtime goal in the Conference Finals Game 6, then he scored a hat trick in Game 7. This trade goes down in history beyond the Kings, but at the end of the day, this is LA’s biggest move in franchise history.

NHL history: Best trade in Minnesota Wild history

The Minnesota Wild have made a lot of huge moves in free agency. They signed Zach Parise and Ryan Suter to matchup monster contracts in 2012. Niklas Backstrom and Brian Rolston were two very good signings that came in the first decade of the team’s existence. When it comes to trades, there aren’t a lot of good ones out there, but one stands out as getting the right player when he needed it most.

Devan Dubnyk had all of the expectations in Edmonton, but he could never live up to it. He made 157 starts for the Oilers before they traded him to the Nashville Predators. He played two games for the Preds before going to the Arizona Coyotes. After putting up some decent numbers in the desert, he was traded to the Minnesota Wild for a 3rd-round draft pick.

He was immediately great. Dubnyk put up a .936 save percentage over 39 games with the Wild that season. He ended up winning the Masterton Award and came in third in Vezina Trophy voting that season. Dubnyk led the Wild to the playoffs that season, and he even won a round.

Dubnyk was the starting goalie for the Wild for the next six seasons, and he put up a save percentage north of .910 in all but one of those seasons. He was in the top five of Vezina voting in one other season, and he saved the Wild from having to worry about that position for a long time.

NHL history: Best trade in Montreal Canadiens history

Montreal Canadiens Get: 1971 1st-round pick, Francois Lacombe
California Golden Seals Get: 1970 1st-round pick, Ernie Hicke

This is the only trade that came between a team that exists and a team that doesn’t exist at all anymore. The Montreal Canadiens were on a mission to get the first-overall pick in the 1971 NHL Draft. That was the pick that ended up being Guy Lafleur, so it’s no wonder they wanted that pick. They had the California Golden Seals’ pick all season, which they thought would be really high, but they had one problem. The Los Angeles Kings were playing worse than the Golden Seals, so the Canadiens made a move to make the Kings, who did not own their own 1st-round pick, better.

It worked, and the Golden Seals secured the first-overall pick. The pick that went to the Seals ended up becoming Chris Oddleifson, who had a really good junior career, never even played a game with the Golden Seals. He started his career with the Boston Bruins and ended up playing the majority of his time with the Vancouver Canucks.

Meanwhile, Guy Lafleur put up 1,246 points in 961 games on his way to a Hall of Fame career. That is just in the regular season. He scored 133 points in 124 playoff games. This led to five Stanley Cup championships. Lafleur was one of the best of this era, and he played for the best teams of all time thanks to some masterful work by Sam Pollock taking advantage of inexperienced new GMs of these expansion teams.

NHL history: Best trade in Nashville Predators history

The Washington Capitals are still hurting from this trade. During the 2013 lockout-shortened season, the Capitals were looking to get an extra boost for the playoffs as they still hadn’t won a Stanley Cup with Alex Ovechkin. In fact, they hadn’t been past the second round. It was time to make a real move towards winning it all. Unfortuantely, the Caps thought Erat was that key, and he clearly wasn’t.

They sent the Predators Filip Forsberg, who was playing in Sweden at the time. He wasn’t in the SHL, but he still made his NHL debut later that year. He never went back to Sweden, and the former 11th-overall pick became a star with the Predators.

Since the trade, Forsberg has 385 points in 497 games played. He has two 30-goal seasons and came close three other times. The Predators got a star for a deadline acquisition. That’s the scary part about trading for a prospect.

Meanwhile, Erat played 62 games with the Capitals in the regular season. What’s worse is the Capitals were kcocked out of the first round of the playoffs by the Rangers in 2013. Erat scored zero goals in the playoffs, and only played four games. The Caps traded him next season to the Coyotes for Rostislav Klesla, Chris Brown, and a 4th-round pick. It is what the kids call an “epic fail”.

NHL history: Best trade in New Jersey Devils history

Toronto Maple Leafs fans still talk about this deal today. Steve Dangle mentioned this deal on one of his podcasts in July. The Leafs traded for Tom Kurvers to bolster their roster in 1989. The New Jersey Devils had been pretty awful up until a run to the 1988 Conference Finals. 89 was back to the basement for the Devils, and relatively new GM Lou Lamoriello needed to build up the prospect pool.

Honestly, there’s a chance this deal could have been even worse. The ramifications of this deal actually impact five different franchises. The Devils traded Kurvers to a Maple Leafs team looking to make an impact. But instead of trading for their 1990 1st-round pick, they took their 1991 1st-round pick. That was the famous Eric Lindross draft. The Leafs thought they’d continue to be good, so that wasn’t a problem.

Well, until it was. The Leafs were terrible in 1990-91, and they didn’t have their own 1st-round pick. The Leafs were at the bottom of the standings when they made a trade with the Quebec Nordiques to actually get them to tank. This allowed Quebec to get the first pick, which they would take Lindross, who then refused to go to Quebec and demanded a trade. He ended up going to Philadelphia, despite the fact the Rangers thought they got Lindross. Neither of those deals would happen if the Devils got Lindross and if the Maple Leafs didn’t make moves to keep themselves from being the worst team in the league.

The Devils ended up getting the third-overall pick. They used that pick to get the best defenseman in the draft, Scott Niedermayer. Niedermayer would become one of the best offensive defensemen in the history of the league. He, combined with Scott Stevens and Martin Brodeur, became a Hall of Fame trio that won three Stanley Cup Championships. Niedermayer came back and won a fourth Stanley Cup with the Ducks. He had a fabulous career, and Kurvers was traded the very next season.

NHL history: Best trade in New York Islanders history

The New York Islanders put together a dynasty mostly with shrewd moves and great drafting. It was the move they made at the 1980 trade deadline that kicked off their dynasty. Butch Goring had a long-term deal already signed with the Los Angeles Kings, but in a shocking move, they traded him for Bill Harris and Dave Lewis.

Goring was livid when the Islanders traded for him. He thought he was going to build a life in LA, but things changed pretty quickly. The face of a franchise in need of one just sent the one guy they had across the country, and the Islanders were off.

Goring and the Islanders won the next four Stanley Cup Championships. The dynasty might not happen without him. He scored 19 points in the 1980 playoffs and 20 points in the 1981 postseason. He was a very important part of the franchise, playing in 99 playoff games in just five seasons with the Islanders.

Meanwhile, Harris was a former first-overall pick who didn’t really make an impact with the Kings. He played just over 100 games before he was traded again. Lewis was a pretty good player, but his impact was never going to be that of a star. He was a complementary player that they traded someone who made a dynasty for. On paper, it wasn’t bad in the beginning, but they ended up regretting it in the end.

NHL history: Best trade in New York Rangers history

The Edmonton Oilers are known for trading its stars. Obviously, the Wayne Gretzky trade was the one that will live on forever, but the trade that Rangers fans will always remember is the one that sent Mark Messier to Broadway. Messier was already a star with five Stanley Cup Championships to his name. The Oilers were trying to get the most out of its stars now that the dynasty was over.

Messier was holding out during the 1991 offseason. It wasn’t his first holdout, and it wouldn’t be his last, but this one was the last straw for the Oilers. They traded him right before the season. Messier was immediately the shot in the arm the Rangers needed. They won the President’s Trophy that season.

Messier became the most popular athlete playing in the World’s Most Famous Arena. He played at the same time as Patrick Ewing, but the fact he brought a championship to New York for the first time in 50 years, and the fact he did it with a guarantee, a hat trick in an elimination game, and then a couple of Game 7 wins to bring the Stanley Cup down Broadway.

For Messier, the Oilers got Bernie Nicholls, who lasted a season and a half in Edmonton, Louie DeBrusk never scored more than 10 points, Steven Rice was traded three years later, and David Shaw was traded that same season. The Oilers got nothing of note from the Messier and Gretzky trades. That’s like if the Oilers traded Connor McDavid and Leon Draisaitl for some prospects who never worked out and some bottom-six players.

NHL history: Best trade in Ottawa Senators history

Alexei Yashin was supposed to be a superstar. He was the first player the Ottawa Senators ever drafted. Eventually, he came over from Russia and played alongside fellow number-one overall pick Alexandre Daigle. He scored 79 points in his first season and was considered for the Calder Trophy. He quickly became a star, and he was even named team captain. Unfortunately, the Senators weren’t very good to Yashin. They clearly liked Daigle better, and they made it known.

It led to a lot of stress for the Senators and their star player, especially when Daigle was clearly a bad pick. Yashin would have been a great player if he could just keep his head on straight. A failed $1 million hospital donation, multiple disputes with upper management, holdouts to get a better deal, and being suspended for an entire season led to the Islanders calling to add the star.

The Isles were looking to finally come back to their winning ways of the 80s. The 90s were not very kind as the Devils and Rangers quickly lapped the franchise in the New York media market. They sent monster defenseman Zdeno Chara, bottom-six forward Bill Muckalt, and a 1st-round pick.

That 1st-round pick ended up being the second overall in 2001. The Islanders could have used that to take Jason Spezza, but instead he went to Ottawa. We know how Spezza’s career went. He played 11 years in Ottawa, putting up 687 points in the process. Meanwhile, Yashin spent five tumultuous years on the Island where he couldn’t bring the franchise back from the dead. He went back to Russia with multiple rumors saying he could come back, but he never did.

NHL history: Best trade in Philadelphia Flyers history

Yet another example of the Toronto Maple Leafs making the wrong move that helps a franchise establish itself. This time, the Philadelphia Flyers were let out of their own mistake by getting back a player they traded once before. Bernie Parent is the catalyst to the best era of Flyers hockey. However, they traded him in his prime to Toronto in a deal to get Rick MacLeish.

Parent eventually left Toronto to play for the Miami team in the WHA. When the Miami team never worked out, all of the team’s players were given to the Philadelphia Blazers, which worked out that he was going back to the team he dominated with.

He quickly realized this was not the right move as the league had basically no defense. He left in the playoffs and hoped to return to the NHL, but he did not want to go to Toronto. So, they traded his rights back to Philadelphia.

Parent went on to play six more seasons in Philadelphia. In his first two seasons back in the City of Brotherly Love, Parent led the Flyers to back-to-back Stanley Cup Championships. He was also insane in the playoffs. In 1973, he put up a .933 save percentage. The next season, he allowed less than two goals per game on his way to Cup number two. There was nobody playing as well as Parent, and he showed the Flyers weren’t going to be denied. Parent won two Conn Smythe Awards and two Vezina Trophies in the same seasons. It might be the most dominant two-year span by any goalie ever. And it happens because the Flyers realized their mistake.

NHL history: Best trade in Pittsburgh Penguins history

This one is a draft trade where the Pittsburgh Penguins knew what they wanted and made a very shrewd move to make it happen. The Florida Panthers got the first-overall pick in the 2003 NHL Draft. The Pittsburgh Penguins were desperate for a goalie. They knew Marc-Andre Fleury was at the top of the draft, and while first-overall goalies aren’t exactly a given (cough, cough, Rick Dipietro), the Pens were willing to give this a chance.

It was well worth the cost. The next season, they would get the second-overall pick and take Russian center Evgeni Malkin. One season later, the Penguins would get the number-one overall pick that just happened to be Sidney Crosby. So, they now had their goalie, and two centers to build a dynasty with. It obviously took longer than they expected, but it did come.

Fleury’s time in Pittsburgh was tumultuous, but his impact is undeniable and the fanbase would take him back at a moment’s notice at this point. He played 13 seasons in Pittsburgh, and after his first two seasons where he was basically a teenager, he never saw his save percentage below .905. He helped the Penguins win three Stanley Cups (although, Matt Murray was also helping in two of those), and now he’s once again dominating in Vegas.

The Penguins gave the Panthers the third-overall pick, their 2nd-round pick, and right wing Mikael Samuelsson. Samuelsson lasted one season before going overseas during the lockout and not coming back for three years. The third-overall pick turned into Nathan Horton, who was fine. The 2nd-round pick became Kamil Kreps. If the Panthers forced the issue and took the Penguins’ own 2nd-round pick, they could have taken Loui Eriksson, just to spread a little more salt in the wound.

NHL history: Best trade in San Jose Sharks history

There are few trades in the history of the NHL that look as bad as this one. It’s crazy that the Bruins made the Tyler Seguin trade after the mistakes of the Joe Thornton trade. This trade completely flipped two franchises on their heads, and it made the San Jose Sharks one of the catalysts of the Western Conference for a decade.

Coming out of the NHL Lockout, the Bruins were very bad. Thornton was clearly a superstar, but the Bruins didn’t have much around him. With 33 points in 23 games to start the season, the Bruins looked at their 26-year-old center and decided it was best for them to move him. Sometimes that’s the right idea. Their value is extremely high, they will need a huge contract soon, and the assets they get in return will help build the next era of the franchise. Just look at the Avalanche after trading Duchene.

Well, that doesn’t happen when the assets going the other way are Wayne Primeau, Brad Stuart, and Marco Sturm. None of those players did much of anything in Boston. The Bruins didn’t even get a draft pick in the deal. Not one draft pick. They held no control of the situation. If they got the Sharks 1st-round pick, they had a chance to draft Claude Giroux to pair with Phil Kessel.

Thornton went on to play for 15 years in San Jose. He became an absolute points machine. He had more than 1,000 points in San Jose alone. He is still playing in the NHL 16 years later, and he might sign with another team well into his 40s. Heck, maybe he will sign in Boston this time.

NHL history: Best trade in St. Louis Blues history

Some of these are obvious, and there is probably no trade more obvious than the Flames trading Brett Hull to the St. Louis Blues. The son of Bobby Hull was on his way to superstardom, and the Flames traded him in the middle of his rookie season. It is hard to fathom just how dominant Hull became in St. Louis.

He went on to play 11 seasons in St. Louis. Hull scored a ridiculous 936 points in 744 games. He scored 527 goals with the Blues alone. This trade was insane from the start, and Hull made the Flames seriously pay for giving up on him. He became the star of St. Louis. Honestly, his career as a whole is underrated. He broke 70 goals three seasons in a row, and he scored a ridiculous 86 goals in 1990-91.

Rob Ramage was fine for the Flames and he was a part of the team’s 1989 Stanley Cup Championship. However, he left right after that to go to Toronto. So, he only played 80 games in Calgary. Rick Wamsley was a backup for parts of five seasons and only appeared in one game during the 1989 playoffs.

This is for a Hall of Famer. The Blues took advantage of a situation in the middle of a season. Funny enough, Blues fans and reporters did not like the deal at the time because the Flames took one of their gritty defenders for an “unproven” player, but looking at their seasons, it had to be more than that. The Blues lost a trade pretty badly sending St. Louis Eddy Beers, Charles Bourgeois, and Gino Cavallini for a package that included Joe Mullin. This didn’t work out like that trade, and the Blues had a franchise star for more than a decade.

NHL history: Best trade in Tampa Bay Lightning history

This deal was very hard for Tampa Bay Lightning fans. Martin St. Louis was the heart and soul of this franchise for 13 years. He helped them win a Stanley Cup, he was part of the original core that built what is a great NHL fanbase in a non-traditional market, and he was an inspiring story, going from an afterthought undrafted player to a Hall of Famer. However, in 2014, it’s clear that the Lightning were heading towards a rebuild, and they needed to sell their star for assets. Boy, did they get some assets.

The Rangers sent the Lightning Ryan Callahan, a 2014 1st-round pick, and a 2015 conditional 1st-round pick. Callahan played the final six years of his career in Tampa and played the role as a glue guy. He was imperative in lifting the Lightning to where they are now, and it’s honestly upsetting he wasn’t able to be a part of this back-to-back Cup team.

The draft picks are a little harder to keep track of, but just know they didn’t make either 1st-round pick because they traded down both times. However, the trades they made turned into Anthony Cirelli, Dominik Masin, and Mitchell Stephens. Cirelli is now one of the great young players on this Lightning roster. He was one of four players they protected in the Seattle Kraken expansion draft. This is going to be the center that pushes them into the next era.

The Lightning are now a powerhouse. While this trade didn’t provide them with a super duper star, getting this big of a haul for St. Louis when he was looking to go to a contender is impressive.

NHL history: Best trade in Toronto Maple Leafs history

Imagine if this deal happened in the Twitter era? One quick caveat, this deal was with the Quebec Nordiques, not the Avalanche. Anyway, the Toronto Maple Leafs sent one of their fan favorites in Wendel Clarke along with a massive package to get a massive package. The main piece is obviously Mats Sundin. He became the Maple Leafs in the 90s and early 2000s.

Sundin was already awesome. He had a 114-point season under his belt, and he was just 23 years old at the time of the trade. Sundin would go on to play 13 years in Toronto, scoring more than a point per game over 981 games. This was such a good trade for the Maple Leafs just looking at getting Sundin alone. Even if the Nordiques got good players in return, this would be a massive win for the Maple Leafs.

The problem for Quebec is they didn’t get good players. Clarke was gone after one year. Sylvain Lefebvre was a fine bottom-four defenseman during his five years with the franchise. Landon Wilson played 16 games with Quebec before they traded him to Boston, where he continued his 10-year career.

The saving grace had to be the pick swap. Wait, the Nordiques gave up the 10th-overall pick in this deal and got back the 22nd-overall pick? Toronto just keeps on winning. They traded the 10th-overall pick in a deal to get the Capitals 1st-round pick and Mike Ridley. He only lasted one year in Toronto, but that’s still more games than Jeff Kealty who never made it past the IHL.

NHL history: Best trade in Vancouver Canucks history

Markus Naslund was once a linemate of Mario Lemieux and Jaromir Jagr. The Pittsburgh Penguins thought they had something great as Naslund would show flashes of brilliance, but he was wildly inconsistent. The 1991 1st-round pick was given a real shot to show what he was worth in the 1995-96 season. He didn’t play terribly, putting up 52 points in 66 games, but previous years of inconsistency and the hope he’d lift his game even more made a trade inevitable.

The Penguins did have a good player, but the fact that they were looking to move him took a lot of the power from them. They traded him for Alek Stojanov, who ironically was actually drafted ahead of Naslund in the 1991 draft. This is more bad luck by the Penguins, and if Stonjanov never gets traded he might grow into a good player, but he got into a car crash that basically ended his career.

Meanwhile, Naslund became a star in Vancouver. Maybe it was living in the shadow of Jagr and Mario, but things just seemed to fit better in Vancouver. It seemed like he was able to breathe again. Naslund would go on to play the next 12 years in Vancouver, putting up 756 points in the process. He peaked in 2003 when he won the Pearson Award and came in second for the Hart Trophy to  Peter Forsberg.

Naslund could have been a superstar in Pittsburgh, but playing for the Penguins in the mid-90s meant following along with the two-headed monster that was Jagr and Lemieux. Naslund wasn’t able to deal with that for whatever reason, but he found his stride in Vancouver. The Canucks are more than happy it worked out the way it did.

NHL history: Best trade in Vegas Golden Knights history

Obviously, there isn’t a long history of moves from the Vegas Golden Knights, but they made a surprising amount of trades and a lot of them were massive. The move to bring in Nolan Patrick for Cody Glass, a swap of former 1st-round picks, was the 39th trade in franchise history. While they made huge deals for Mark Stone, Tomas Tatar, Max Pacioretty, and Robin Lehner, it was the mastery they pulled at the expansion draft that tops everything.

Vegas dominated the expansion draft more than anyone could know. They made ten (!!!) trades during the draft. The Seattle Kraken weren’t able to make even one during the draft because of Vegas completely taking the NHL’s lunch in 2017. The best move they made by far was the fleecing they did of the Florida Panthers.

The Golden Knights were already going to take Jonathan Marchessault. He was coming off a 30-goal season, and for some reason, the Panthers felt he was expendable.  Okay, this is already a bad decision, but many GMs made bad decisions at the expansion draft. What took the Panthers to the next level was basically giving away Reilly Smith on top of it.

Smith had an expensive contract, but he was a very useful player. He is always going to be slightly inconsistent, as one can tell by Smith scoring 27 goals in 71 goals in 2019-20 and then coming back with just 14 goals last season. However, losing him for a 4th-round pick is not good asset management. The Knights have kept both Marchessault and Smith for this great run.

NHL history: Best trade in Washington Capitals history

Trading 1st-round picks is risky business. If you don’t realize that as we are on team 30 of this list, then you need to learn it now. The Philadelphia Flyers were looking to get a shutdown defenseman, and they thought Steve Eminger could grow into that role. He played with Mike Richards in junior, so that seems to be a reason the Flyers pulled the trigger. They also got a 3rd-round pick in the deal. Sometimes, you have to take risks to get good players.

Unfortunately for the Flyers, that 1st-round pick was 27th overall in the 2008 draft. This seems like a best-case scenario, right? It’s not a lottery pick, so the Capitals’ odds of picking someone great is… oh. They took John Carlson.

John Carlson is now one of the best offensive defensemen in the league. He is the top-line guy the Flyers have been looking for forever. Since they offered Shea Weber an offer sheet, the Flyers have been looking for a number-one defenseman. They could have just used the pick to take Carlson and all of this would have been solved. He could have played with Ivan Provorov for the next five years.

Carlson is 12 years into his career with the Capitals. He played 809 games and scored 522 points as a defenseman. During the Capitals run to the Stanley Cup, Carlson scored 20 points. His four power-play goals made that unit such a threat beyond Alex Ovechkin. This entire move just put the Capitals on another level.

NHL history: Best trade in Winnipeg Jets history

We end things with an addition by subtraction trade for the Winnipeg Jets. Evander Kane was the Jets’ star back in 2015. However, he just kept putting his foot in his mouth. Some of it is small stuff like an Instagram post holding a stack of cash or saying something dumb to the local media. There were other rumors that there was a clear issue in the locker room. Either way, the Jets needed to get out of this relationship.

The Buffalo Sabres were there looking for a star, and they sent a pretty hefty package to the Jets to make it work. They got a massive defenseman in Tyler Myers who really hit his stride in Winnipeg. Joel Armia was a decent bottom-six forward for a few years before going to Montreal. Drew Stafford gave the Jets a needed veteran presence and played parts of three seasons before he was traded to Boston. Brendan Lemieux was traded to the Rangers after a year and a half with the Jets.

The Jets used that 1st-round pick to get Jack Roslovic. He played a few seasons before the Jets paired him with Patrik Laine to get Pierre Luc-Dubois, the number-one center they were desperately looking for. There is a lot of pieces to this deal, and the Jets are very happy with their return.

The biggest part of this deal is getting out of the Evander Kane debacle. He has since been traded to the San Jose Sharks who then gave him a mistake of a contract extension. Now, they are looking to trade him again, but there won’t be many takers.