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Sometimes when relationships deteriorate between a player and their team, they part each other's company in great haste to minimize damage. Other times, they absolutely do not do that, and the NHL has seen its fair share of dramatic breakups over the years.
With Dylan Larkin and Connor Hellebuyck each seeking new teams to play for, it got us digging into our memories about other times when a star player wanted a change of address only to find out it wasn't going to be as easy as they thought it would. After all, teams don't want to lose an elite player, and players don't want to deal with what's irking them any longer.
Larkin and Hellebuyck aren't alone and we know they won't be the last players to demand a trade, but where do their yet-to-be-settled situations rank out right now with some of the other legendary situations? Let's dig in and compare.
If you weren't old enough or not even born yet to witness Pavel Bure's NHL career, boy, did you miss out on something special. When the "Russian Rocket" arrived on the scene with the Vancouver Canucks in 1991, he took the league by storm with his blazing speed and electrifying goal scoring.
Bure helped lift the Canucks during his time there and helped lead them to the Stanley Cup Final in 1994 where they came within one win of bringing the franchise its first title. But after seven seasons, Bure wanted out thanks to issues with the team and the pressure of playing in Vancouver. Unfortunately for Bure, the Canucks GM at the time was Brian Burke and he wasn't about to get bullied by his star player.
When training camp opened in fall 1998, Bure remained home in Moscow and Burke remained adamant that he didn't agree with the player's reasons for wanting to leave. But after months, eventually Bure got his wish and was traded to Florida in a blockbuster deal in January 1999. Although Bure dazzled with the Panthers, injuries conspired to shorten his career. Meanwhile, the Canucks were able to draft Henrik and Daniel Sedin in the 1999 Draft and course correct the franchise.
Time helped patch things up between Bure and the Canucks franchise and the team ultimately retired his No. 10 in November 2013.
When Dany Heatley joined the Ottawa Senators following the 2004-05 lockout, he went from being an outstanding offensive weapon in Atlanta to a goal-scoring monster there. For four seasons, Heatley exploded in Ottawa twice scoring 50 in a season and posting 41 and 39 goals in his other seasons.
The 39-goal season in 2008-2009 is the one that stands out because the Senators missed the playoffs and Heatley was unhappy about then head coach Cory Clouston. Heatley thought his role on the team was less than it ought to be. Although Clouston admitted to taking Heatley off the team's first power play, he cited needing the team to improve in general and didn't intend to slight the star winger.
The reasons fell on deaf ears with Heatley who demanded a trade and was dead set on using his no-trade protection to pick where he wanted to go. There was a trade set with Edmonton that he blocked, and Heatley ultimately went to San Jose in blockbuster in September 2009. There, he scored 43 goals in his first season with the Sharks but his production quickly slipped in the years to come and retired in 2015.
It took 15 years for Heatley to be welcomed back to Ottawa, however, when the team reunited the trio of Heatley, Jason Spezza and Daniel Alfredsson for a special night to honor the once dominant line in 2024.
If you thought it was challenging for Dylan Larkin and the Red Wings to find a new team in a trade, think about how much harder it is for 33-year-old goalie Connor Hellebuyck and the Winnipeg Jets to find a new deal.
Hellebuyck has been a bit freer with his options of where he'd like to go despite having no-trade protection, but with five years left on his contract and an $8.5 million cap hit for a player his age and a position as demanding as goalie, finding the right team with the need, want and payroll flexibility is much more difficult.
Hellebuyck dealing with a GM as strident in his ways as Kevin Cheveldayoff helps add intrigue because he's not as gung-ho in making trades and with Winnipeg playing well to start the season, the pressure to get a deal done isn't there so long as Stuart Skinner and Clay Stevenson are holding things down and other NHL teams sort through their own goaltending situations.
It remains to be seen how Dylan Larkin's trade request and saga will turn out for both him and the Detroit Red Wings, but one thing is for sure, the nightly drama of watching him continue to play for them until a trade happens makes us watch intently.
Larkin's request for a trade in the summer followed by a short list of teams he'd approve of going to reminded us of Dany Heatley's exit in Ottawa, but Heatley never had to play more for the Senators after asking out. Seeing Larkin get booed routinely on home ice is so deeply awkward and undoubtedly wherever he lands next, the game to be at will be his first one upon returning to Detroit.
While Larkin has the hammer, so to speak, with his ability to block trades, being a high-priced player with term on a contract and being 30 years old creates more pitfalls to finding a new team. It's easy to get traded, it's not so easy when the market is artificially limited.
What happened with the Winnipeg Jets and Evander Kane wasn't quite like what went down with other players on this countdown. There was always speculation he wanted out only to have it denied by everyone and even up until the day he was traded it was never apparent if he asked to be moved.
But when Kane was traded (while injured and out for the rest of the season) in 2015 to the Buffalo Sabres, the days leading up to the move brought out plenty of rumors about how the situation for him in Winnipeg soured bitterly. There were rumors of discord with teammates, of his clothes being tossed in the showers, and all sorts of general uneasiness.
The Jets found a team willing to be OK with him not playing the rest of the season in the Sabres (who were trying to sink to the bottom of the league to try and draft Connor McDavid) and were able to get players for themselves that helped immediately (Tyler Myers, Drew Stafford, Joel Armia, a first-round pick) and unloaded Kane and Zach Bogosian to Buffalo.
The Jets eventually got to the playoffs without Kane and Kane wouldn't reach the postseason for the first time in his career until 2018 when he was traded by the Sabres to San Jose.
The cut-and-dry of what happened between Jack Eichel and the Buffalo Sabres was built for drama. After all, the Sabres selected him with the No. 2 pick in 2015 after sinking to the bottom of the league and while Eichel was the centerpiece of their efforts rebuild, the urge to make results happen ASAP helped undo what should've been a great partnership between player and team.
During Eichel's six seasons in Buffalo, the Sabres went through three general managers (Tim Murray, Jason Botterill and Kevyn Adams) and he played for four coaches (Dan Bylsma, Phil Housley, Ralph Krueger and Don Granato) and the best season they had in that time was his rookie season in which they had 81 points.
The breaking point for Eichel came after Botterill was fired in 2020 and he, quietly, asked to be moved. Adams, who just came on as GM, did his part to try and convince him to stay by adding veterans Taylor Hall and Eric Staal, but after Eichel injured his neck during the 2020-2021 season, his desire to get a kind of surgery the team didn't approve of proved to be a bridge too far.
Eichel was dealt to Vegas in a blockbuster that sent Alex Tuch, Peyton Krebs and a first-round pick (that became Noah Östlund) where he went on to win the Stanley Cup in 2023 and continues to lead them as annual Cup contenders. The Sabres, meanwhile, broke a 15-year playoff drought in 2026 thanks to all three players they acquired in the deal and everyone is satisfied with how things played out, even if Eichel always gets booed every time he returns to Buffalo.
Sometimes issues with a player and a team come up out of the blue and then there are others where things got murky and stayed that way. That might be the best way to describe how things dissolved between Ilya Kovalchuk and the New Jersey Devils.
The partnership between Kovalchuk and New Jersey seemed natural given that he was traded there by the Atlanta Thrashers in February 2010 and happily negotiated a new contract to remain a Devil for life.
The first contract he signed with them was nixed by the NHL and led to the Devils being punished for trying to circumvent the salary cap because of the 17-year, $102 million deal the two sides agreed to. They eventually signed a 15-year, $100 million contract after that and all was well... right?
Not exactly. Although Kovalchuk was outstanding in New Jersey and helped lead the Devils to the Stanley Cup Final in 2012, he abruptly retired from the NHL and went back to Russia to play in the KHL in 2013. That allowed the Devils tear up the monster contract and move on.
Although Kovalchuk eventually came back to the NHL in 2018 with Los Angeles. Upon returning to New Jersey for the first time, Kovalchuk was booed throughout the game. Turning your back on New Jersey comes at a cost and in his case, he gave up 12 years and $77 million to go back home.
Although Brendan Shanahan wasn't a Hartford Whaler for a long time, his legacy there was one fans there wish they could forget.
Shanahan joined the Whalers in 1995 when he was acquired from St. Louis in a trade for young defenseman Chris Pronger. Although Pronger was just 20 when he was traded, Hartford landed a two-time 50-goal scoring power forward for him and felt like they changed things for the better for the franchise and during his one full season with the Whalers, Shanahan delivered. He had 44 goals and led the team with 78 points.
But Shanahan wasn't happy in Hartford. At all. Despite being named captain, he asked for a trade during the summer because of general unhappiness and rumors about the franchise relocating. He wasn't traded before the season started and he gave up the "C" in the process. On October 9, 1996, he was dealt to the Detroit Red Wings for Paul Coffey and young power forward Keith Primeau.
Shanahan proved to be the missing piece for the Red Wings and helped lead them to back-to-back Stanley Cups in 1997 and 1998. The Whalers, meanwhile, lost Pronger and Shanahan and despite Primeau being a very good player, he didn't compare. Making matters even worse, the Whalers packed up and moved to Carolina after the 1996-1997 wrapped up.
We don't see draft pick drama much these days in the NHL, but when there's a story as big and as juicy as Eric Lindros's with the Quebec Nordiques, every other draft story takes a back seat.
Lindros was set to be the top pick in the 1991 NHL Draft, and the competition wasn't even close. He was the biggest and best forward and everyone knew it, especially the Quebec Nordiques who owned the top pick. Lindros and his family knew the Nordiques would pick him but let it be known that he would not play for Quebec no matter what. Nordiques management called his bluff and selected him with the first pick.
A year later at the draft, Quebec worked to trade Lindros's rights and managed to make two separate deals with the New York Rangers and Philadelphia Flyers. After the case was sent to an arbitrator, the Flyers were deemed to have agreed to the trade first and the blockbuster deal went through. Lindros headed to Philly and Peter Forsberg, Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, a first-round pick (that became Jocelyn Thibault) as well as Chris Simon and Nolan Baumgartner headed to Quebec.
Upon Lindros's first trip to Quebec to play against the Nordiques, he was booed in a way no NHL player has been booed since. He was taunted by fans with pacifiers and signs in French and English cursing him out. The Flyers made it to one Stanley Cup Final with Lindros, meanwhile the Nordiques moved to Denver to become the Colorado Avalanche and, buoyed by many of the players they received for Lindros, won the Cup for the first time in 1996.
One of the swiftest and most public beefs in hockey history all unfolded in front of our eyes in 1995 when Patrick Roy, a two-time Stanley Cup winner with the Montréal Canadiens, was left in to suffer nine goals against in an 11-1 loss to the Detroit Red Wings on December 2, 1995.
Coach Mario Tremblay, who just became coach earlier that season after Jacques Demers was fired four games into the season, left Roy in the game to take a beating on home ice. After allowing the ninth goal, Roy pulled himself from the game, skated to the bench and told management, seated behind the Canadiens bench, that he would never play for the franchise again.
Four days later, Roy was traded to the Colorado Avalanche, the former Quebec Nordiques, with Mike Keane for Martin Rucinsky, Andrei Kovalenko and Jocelyn Thibault.
Roy's legacy is legendary as he went on to win two more Cups with Colorado including one immediately upon arrival in Denver and helped solidify that franchise for good. The Canadiens, meanwhile, parted ways with Tremblay after the following season in 1997 and have been back to the Stanley Cup Final once since Roy was traded.
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