*This article was originally published in Aug. 2021
The National Hockey League is a professional sports league and a business at the same time. The lines often get blurred, especially regarding the team’s finances. Whether signing big free-agent players, launching new jersey designs, hiring new staff, or orchestrating blockbuster trades to rebuild a pretender into a contender, the business side merges with the on-ice product you and I love so passionately.
Wearing the “C” is a player’s most significant individual achievement because that player earned the respect of the coaching staff, upper management, and fellow peers. They are someone other veterans listen to, the young guns look up to, and the coach relies upon to fire up the troops at a moment’s notice.
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Usually, the captain is one of the best players and carries a hefty contract. Sometimes the moment arises when that player is made available to change the franchise’s direction, and despite being a leader, they find themselves headed to a new city. Ultimately, no player is untouchable, so when we look back at the history of trades, it is no surprise that some of the game’s greatest leaders have ended up on a new team.
15. Chris Chelios – June 29, 1990
The Montreal Canadiens are one of the most respected franchises in professional sports history. Thanks to 24 Stanley Cup championships, they remain one of the most revered teams in hockey. In the second round of the 1981 NHL Entry Draft, the team selected future Hall of Fame defenceman Chris Chelios. He was the backbone of a team that won in 1986 and lost in the Final in 1989. Furthermore, during the 1988-89 season, he was named the best defender in the league by earning the James Norris Trophy.
After losing to the Calgary Flames in 1989, longtime franchise great Bob Gainey retired, leaving the captaincy vacant for the first time in eight seasons. According to an exciting story about the voting process, Chelios emerged as a new co-captain alongside Guy Carbonneau. The two players were in the prime of their careers and, despite different leadership styles, managed to co-exist for an entire season, splitting the duties.
Related: The Chris Chelios Trade Revisited
Just one season removed from an appearance in the Stanley Cup Final, the Canadiens bowed out early in the second round of the playoffs, causing some changes in the team’s personnel. In one of the league’s most shocking trades, the Canadiens moved on from their Norris Trophy winner, Chelios, shipping him, along with a second-round pick in 1991 (Michael Pomichter), to another Original Six franchise, the Chicago Blackhawks, for Denis Savard in June 1990. Meanwhile, Carbonneau would lead the Canadiens to another Stanley Cup title in 1993, while Chelios would earn two more Norris Trophy wins in the next six seasons.
14. Dion Phaneuf – Feb. 9, 2016
Edmonton native Dion Phaneuf began his career in 2005-06 with the Calgary Flames. The veteran of 1048 games served as an alternate captain with the Flames before a trade in January 2010 landed him in Toronto with the Maple Leafs. Within five months, Phaneuf was named the 18th captain in franchise history.
Unfortunately, Phaneuf was the leader of one of the darker periods of the Leafs’ history, advancing to the playoffs just once in his seven years in blue. Fans will never forget that one playoff series (2013) since the team suffered one of the worst collapses in hockey history during Game 7. The Leafs held a 4-1 lead over the Boston Bruins with just 14:31 left in the third before losing 5-4 in overtime. That game marked the last time the Leafs played in the postseason until 2017.
The Leafs, under their fourth coach in six seasons, decided to trade their captain to their provincial rivals, the Ottawa Senators, in February 2016. In one of the bigger deals in club history (nine players), the Leafs sent Phaneuf, Matt Frattin, Casey Bailey, Ryan Rupert, and Cody Donaghey to the Senators in exchange for Jared Cowen, Milan Michalek, Colin Greening, Tobias Lindberg, and a second-round pick in the 2017 NHL Entry Draft (Eemeli Rasanen).
13. Eric Staal – Feb. 27, 2016
The Carolina Hurricanes were on the cusp of greatness during the 2003-04 season before a lockout would cancel the entire 2004-05 campaign. Eric Staal debuted that year (2003), racking up 31 points in 81 games. Two years later, Staal exploded for 100 points in 2005-06, guiding the Hurricanes to their only Stanley Cup championship.
Current head coach Rod Brind’Amour led the Hurricanes on the ice from 2005 until 2010, when the franchise announced Staal as their new captain. He was the franchise’s young face and quickly climbed the team’s all-time leaderboards in points and games played. However, outside of Staal’s performance, the team struggled for years, failing to qualify for the playoffs from 2010-2018.
In 2016, then-general manager Ron Francis, considered the best player to ever play for the franchise, traded away his 31-year-old captain to the New York Rangers. Carolina swapped Staal for Aleksi Saarela and a pair of second-round picks in 2016 (Artur Kayumov) and 2017 (Luke Martin).
12. Jack Eichel – Nov. 5, 2021
The Buffalo Sabres drafted center Jack Eichel second overall in the 2015 NHL Entry Draft with hopes that he would be the foundation for the future. He made his debut a few months after the draft as a 19-year-old who would score 56 points in 81 games. The future was bright for Eichel and the Sabres, but they needed more pieces to support their crown jewel.
Eichel played six seasons with the Sabres, and despite how skilled he was, he developed a reputation for being injured, and missing time hurt his production. In one of the wildest stories ever told, Eichel needed surgery for a herniated disc in his neck. However, the team didn’t support their captain, and the inner struggles of handling the injury made headlines across the league. Furthermore, the team refused to budge on their stance, which soured the relationship with their star player.
Since the two sides stood at a standstill and couldn’t agree on a procedure, Eichel’s name popped up in the rumor mill. After months of battling, and with the drama playing out in the media, the Sabres traded their captain to the Vegas Golden Knights in November 2021. The Sabres packaged Eichel with a third-round pick in 2023 in exchange for Peyton Krebs, Alex Tuch, a first-round pick in 2022 (Noah Ostlund), and a second-round pick in 2023.
11. Claude Giroux – March 19, 2022
The Philadelphia Flyers found their future captain, Claude Giroux, with the 22nd overall selection in the 2006 NHL Entry Draft. The native of Hearst, Ontario, made his professional debut as a 20-year-old in 2007-08 and was a rookie in a club loaded with veterans. Giroux and the Flyers were in the Stanley Cup Final within two seasons, losing to the Chicago Blackhawks in six games.
The team slowly began to tumble in the standings, and those veterans found new homes and success in other cities. However, Giroux stayed the course and became the Flyers’ 19th captain in January 2013, when the team failed to qualify for the postseason. Despite the team’s lack of success in the playoffs during subsequent seasons, Giroux became the heart and soul of the organization, playing 1,000 games and climbing to second place on their scoring lists.
Despite retooling and rebuilding efforts, the Flyers were not contenders in 2021-22, and with Giroux’s contract set to expire, the two sides needed to decide on the future. In one of the league’s most heartbreaking trades, the Flyers sent their captain to a Stanley Cup contender, the Florida Panthers, in Feb. 2022. Meanwhile, the Panthers parted with Owen Tippett, a third-round pick in 2023, and a conditional first-round pick in 2024 in exchange for Giroux, German Rubtsov, Connor Bunnaman, and a fifth-round selection in 2024.
10. Erik Karlsson – Sept. 13, 2018
Erik Karlsson was one of the best defensemen in the NHL at the beginning of the 2018-19 season. He spent his entire career with the Ottawa Senators, climbing their all-time scoring list while capturing two James Norris Memorial Trophies.
In 2012, Karlsson signed a new seven-year contract with the Senators to play his entire career in Canada’s capital city. The team had decent success with him in the lineup, but by 2018 they had fallen to the bottom of the standings. Four seasons after trading their previous team captain, Jason Spezza, and five years removed from letting Daniel Alfredsson, their captain of 13 years, walk in free agency, the Senators once again let a leader depart.
Karlsson made his way to the West Coast, joining the San Jose Sharks in Sep. 2018. He was part of a trade package that included Francis Perron going to San Jose, with Chris Tierney, Dylan DeMelo, Josh Norris, Rudolfs Balcers, a second-round pick in 2019 (Jamieson Rees), a first-round pick in 2020 (Tim Stutzle), and a conditional second-round pick in 2021 (Zach Ostapchuk) going to Ottawa.
9. Ryan Callahan & Martin St. Louis – March 5, 2014
During the 2013-14 season, the New York Rangers and Tampa Bay Lightning were on different paths. The Rangers had a team ready to win the Stanley Cup with Henrik Lundqvist in the net. Meanwhile, Tampa Bay had failed to make the playoffs in five of the six seasons leading up to the 2014 trade deadline.
The Lightning captain, Martin St. Louis, serving his first season in the role, was unhappy with the situation in Florida. Moreover, he didn’t hide his feelings as the relationship between the star player and team management began to fall apart. When the time came, St. Louis requested a trade to New York, and the team worked out one of the only trades where a team captain got traded for another.
In New York, Ryan Callahan was in his third season as team captain. However, his relationship with the team began to break when they couldn’t agree on a new extension. Unable to solve the problem internally, the Rangers shipped their leader to Tampa Bay. The deal broke down as such: St. Louis and a 2015 second-round pick (Oliver Kylington) went to the Big Apple, while Callahan, a first-round pick in 2014 (Josh Ho-Sang), a first-round pick in 2015 (Anthony Beauvillier), and a seventh-round pick in 2015 (Ziyat Paigin) went south to the Lightning.
8. Mike Richards – June 23, 2011
The Los Angeles Kings had been to the Stanley Cup Final once in their history, with a five-game loss to the Montreal Canadiens in 1993. In the later part of the 2000s, they were stocking up on prospects like Anze Kopitar, Drew Doughty, and Jonathan Quick, to name a few. The stars were aligning, and Los Angeles was on the verge of becoming league kings.
Mike Richards started his career in 2006, and by the start of the 2008-09 season, he was named captain of the Philadelphia Flyers. Philadelphia loaded up on expensive contracts in hopes of their first championship since 1976; however, they lost in the Stanley Cup Final in 2010, causing management to disassemble the core. Richards was a vital member of that team’s nucleus; however, a slide in the standings forced the team to change direction with their captain.
The Kings were a willing trade partner, acquiring Richards and Rob Bordson for a second-round draft pick in 2012 (Devin Shore), Brayden Schenn, and Wayne Simmonds. Within one year of the deal, Los Angeles won its first Stanley Cup and a second title in 2014. Richards was the veteran presence the Kings needed to get them over other powerhouse teams in the Western Conference.
7. Ron Francis – March 4, 1991
When Ron Francis retired from playing, he got into management. After being let go as the Carolina Hurricanes’ general manager, the Seattle Kraken ultimately hired him as their first general manager. The fifth-leading scorer (1798 points) in NHL history was an impact player with the Hartford Whalers during the 1980s, scoring a then-career-best 101 points in 1989-90.
The Pittsburgh Penguins, a team on the brink of the ultimate prize, were still missing a few pieces. The team’s general manager, Craig Patrick, swung a deal with the Whalers, acquiring Francis, Grant Jennings, and Ulf Samuelsson, all important players who put the team in the winner’s circle. Meanwhile, the Penguins traded John Cullen, Jeff Parker, and Zarley Zalapski to Hartford in the exchange.
Within months of this transaction, Pittsburgh hoisted the first of back-to-back championships. Furthermore, Francis grew his legacy with the Penguins, scoring over 100 points twice and becoming the team’s captain when Mario Lemieux retired in 1997. Later, he would return to the Hartford franchise, which relocated to Carolina and led them to their first Stanley Cup Final appearance in 2002.
6. Jaromír Jágr – July 11, 2001
Lemieux was the Penguins’ greatest player from the moment they drafted him in 1984 until his first retirement in 1997. He did everything he could to keep the franchise in Pittsburgh, including buying the team out of bankruptcy in 1999. After everything Lemieux did for the team on and off the ice, Jaromír Jágr took over and dominated the league from 1995-2001, winning five scoring titles.
Jágr was morphing into the second-best player the franchise had ever seen, and many thought he would be the player to lead them to another championship. Unfortunately, things never went that way, and Jágr’s only two Stanley Cup rings came in his rookie season (1991) and sophomore campaign (1992). Francis took over for Lemieux when he retired as a captain; however, Jágr assumed the captaincy in 1998-99 — the first time in his career he had earned such an honor.
When Lemieux returned to the club in December 2000, picking up where he left off, things didn’t work out. Jágr was still the captain but not the main attraction anymore, with his boss playing on his line. He had a hefty contract on the books, and to get out of the financial mess the team found itself in, they traded their captain and reigning scoring champion to the Washington Capitals. Jágr and Frantisek Kucera went to the Capitals for Kris Beech, Ross Lupaschuk, Michal Sivek. Although Jágr didn’t achieve the success he had in Pittsburgh, he did get a new massive contract (seven years, $54 million) with the Capitals.
5. Jarome Iginla – March 27, 2013
Jarome Iginla was the heart and soul of the Calgary Flames, winning a handful of individual awards (Art Ross, Lester B. Pearson, Maurice Richard) during his 16 seasons in Alberta. He remains the longest-serving captain in club history, assuming the role in 2003-04 before a trade to the Penguins in 2013 ended his tenure.
This particular trade hurt the Flames fanbase because they watched Iginla grow from a young man into one of the game’s most respected players. Unfortunately, the team was no longer considered a Stanley Cup contender at this point of his career, failing to qualify for the playoffs for five seasons starting in 2009. Iginla’s only shot at winning a ring came in 2004 when the Flames lost to the Tampa Bay Lightning in a seven-game series.
Facing free agency in the summer of 2013 and uncertain of his future in Calgary, management traded their best player at the deadline to the Penguins. In a three-for-one deal, the Penguins traded a first-round pick (Morgan Klimchuk), Kenny Agostino, and Ben Hanowski for Iginla. For the first time in his career, Iginla had a fresh start and scored 12 points in 15 postseason games as the Penguins lost in the Conference Finals that season. It would be the second to last time one of the game’s best goal scorers would appear in the postseason.
4. Joe Thornton – Nov. 30, 2005
The Boston Bruins drafted Joe Thornton with the first overall selection in the 1997 Entry Draft. At the time, the Bruins were struggling and in danger of losing their contender status after failing to make it deep into the postseason. As finalists in 1988 and 1990, they yielded the Stanley Cup to the Edmonton Oilers. Meanwhile, back-to-back losses in the 1991 and 1992 conference finals were the last hurrah for a team that featured Hall of Famers like Ray Bourque, Cam Neely, and Adam Oates.
The Bruins’ historic playoff run of 39 years ended in 1996-97, signaling a change in the hockey market that was unseen for almost a generation. Thornton would be the franchise’s new face, picking up where Bourque left off whenever he planned to retire. Unfortunately, as you will read later, Bourque was traded, and the Bruins became Thornton’s team much sooner than anyone expected.
Despite Thornton’s successes, the Bruins struggled and never went deep into the playoffs. Consequently, management felt it was time to take the team in a new direction and traded their captain of three seasons out west to San Jose. Meanwhile, the Bruins received Wayne Primeau, Brad Stuart, and Marco Sturm in a three-for-one deal. Thornton then set career highs with 96 assists and 125 points to win the Art Ross and Hart Trophies with San Jose. To this day, Thornton is the only athlete in the four North American sports leagues’ history to be traded and then be named the league’s Most Valuable Player (MVP) in the same season.
3. Mark Messier – Oct. 4, 1991
When you walk into Madison Square Garden and close your eyes, you can probably still hear legendary commentator Sam Rosen yelling, “The waiting is over — the New York Rangers are the Stanley Cup Champions! And this one will last a lifetime!” That moment in hockey history may not have happened if Mark Messier had never requested a trade from the Oilers. (from ‘Mark Messier trade got Rangers the right player at right time,’ NY Post, 06/09/2020)
Messier was a vital part of the Oilers dynasty that won five Stanley Cups titles in seven years, serving as captain during the 1990 playoff run. He was handed the “C” shortly after the Wayne Gretzky trade in August 1988. Instead of playing in the shadow of The Great One, The Moose (Messier’s nickname) finally had the team to himself. Messier proved to the hockey world he was a phenomenal leader who could get results by winning the league’s two Most Valuable Player awards in 1990.
In 1991, the Rangers traded Louie DeDrusk, Bernie Nicholls, Steven Rice, and future considerations (David Shaw) for Messier and future considerations (Jeff Beukeboom). Within three seasons of putting on a Rangers uniform, Messier led the Rangers to their first Presidents’ Trophy (1991), won the Hart Memorial Trophy and Ted Lindsay Award for a second time (1992), then guaranteed a playoff victory before scoring a hat trick, and finally broke the game’s longest championship drought after 54 years.
2. Ray Bourque – March 6, 2000
In one of the league’s most emotional trades, the Bruins traded their longest-tenured player to the Colorado Avalanche. Ray Bourque became co-captain (with Rick Middleton) in 1985-86. He remained in the role until 2000, building a Hall of Fame career. Furthermore, Bourque was a 19-time All-Star and a five-time Norris Trophy winner, finishing his career with 1,579 points, the most for a defenseman.
The trade broke the hearts of every fan in the New England area because the man who gave so much never won the Stanley Cup with the black and gold. He requested a trade with the hope of landing with a contender and achieving the only thing that had eluded him his entire career.
The Avalanche sent Martin Grenier, Samuel Pahlsson, Brian Rolston, and a 2000 or 2001 first-round pick. The Bruins opted for a 2000 pick, selecting Martin Samuelsson. Meanwhile, the Bruins sent Bourque and Dave Andreychuk west to the Avalanche, who lost that season’s conference finals. Andreychuk moved on after the season, missing out on Bourque’s send-off celebration the next spring with the Cup held high over his head.
1. Wayne Gretzky – Aug. 9, 1988
It is no surprise that the trade that sent The Great One from a Stanley Cup champion to a Stanley Cup contender would come in as number one on any list involving notable transactions in league history.
The Oilers traded their captain, the best player in the league, just a couple of months after winning their fourth championship in five seasons. Included in the deal were Marty McSorley and Mike Krushelnyski. Meanwhile, the Kings shipped one of their top prospects, Jimmy Carson, along with Martin Gelinas, and three first-round picks in 1989 (Jason Miller), 1991 (Martin Rucinsky), and 1993 (Nick Stajduhar). Rumors say that Oilers owner Peter Pocklington was in financial trouble, so Los Angeles included $15 million cash in the deal.
Edmonton continued without much interruption, winning the Stanley Cup again in 1990. Since then, the franchise has only been to the Final in 2006, losing a Game 7 nail-biter to the Hurricanes. Meanwhile, Los Angeles became an instant contender but failed in their only Stanley Cup Final appearance with Gretzky in 1993 to the Canadiens.
The trade shocked the hockey world and helped build the league’s reputation in California, which now has three franchises. When Gretzky agreed to the transaction, it showed that no player is untouchable and that the NHL is still a business at the end of the day.
The list of NHL captains traded is pretty long. However, this article highlighted some of the most notable names and the impact those players had on their new teams. Many players depart teams via free agency, but some found themselves in some of the most significant trades in league history.
Furthermore, the game’s greatest player (Gretzky) was dealt twice in his career, meaning anyone is tradeable for the right price. When superstars like Connor McDavid, Gabriel Landeskog, and Steven Stamkos don’t extend their contracts on the first day of eligibility, their names will pop up in the rumor mill. If they end up dealt at some point during their careers, it could alter the structure of this list.