Biggest NHL Trades That Almost Happened

NHL history is replete with trades involving some of the game's biggest names.

From the Edmonton Oilers trading Wayne Gretzky to the Los Angeles Kings in 1988 to the Montreal Canadiens shipping Patrick Roy to the Colorado Avalanche in 1995, those blockbusters had far-reaching effects on the fortunes of the teams involved.

However, there were also several deals involving big-name players of the past and present that were rumored about or were the subjects of trade discussions that never came to pass.

Can you imagine Leon Draisaitl suiting up with the Montreal Canadiens? How about Steven Stamkos joining the New York Rangers during his rookie season or Steve Yzerman getting traded to the Ottawa Senators?

Read on to find out just how close those players were to changing teams and why those deals fell through as we examine the biggest NHL trades that almost happened.

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Quebec-born Hall-of-Fame forwards such as Maurice "Rocket" Richard, Jean Beliveau and Guy Lafleur played major roles in the long and rich history of the Montreal Canadiens. By 2009, however, the Canadiens hadn't had a Quebec scoring star of their magnitude in their ranks since Lafleur's departure in 1984.

Meanwhile, Vincent Lecavalier had gone on to stardom with the Tampa Bay Lightning. Chosen first overall in the 1998 NHL Draft, the Île Bizard, Quebec, native would enjoy 14 seasons with the Lightning, helping them win their first Stanley Cup in 2004, winning the Maurice Richard Trophy in 2007 and finishing among their all-time leading scorers.

By 2009, however, there was front-office turmoil among the Lightning's then-owners Oren Koules and Len Barrie. According to the Montreal Gazette's Stu Cowan, Koules wanted to trade Lecavalier before his 11-year, $85 million contract went into effect for the 2009-10 season. Barrie, however, wanted to retain Lecavalier.

Canadiens general manager Bob Gainey attempted to acquire Lecavalier. Cowan indicated there were reports Gainey offered up Josh Gorges, Tomas Plekanec and Chris Higgins as part of a trade.

Meanwhile, The Hockey News' Ken Campbell reported prospect P.K. Subban and multiple first-round picks were also said to be part of the offer. Sportsnet's Jeff Marek claimed Lightning GM Brian Lawton said the offer was either Subban or fellow blueliner prospect Ryan McDonagh, goalie Carey Price, winger Max Pacioretty and a first-round pick.

As Cowan observed, Barrie ultimately got what he wanted and Lecavalier stayed in Tampa. It's a deal the Canadiens might've regretted. Lecavalier was in decline by that point and would be bought out by the Lightning in June 2013. He retired three years later.

During his 14-season NHL career with the Detroit Red Wings, Pavel Datsyuk became one of the league's greatest all-around forwards. A four-time winner of the Lady Byng Memorial Trophy and three-time winner of the Frank J. Selke Trophy, he helped the Wings win the Stanley Cup in 2002 and 2008, finishing with 918 points in 953 career games.

Datsyuk's tenure with the Red Wings, however, was in question in 2006-07. In the final season of a two-year, $7.8 million contract, he was due to become an unrestricted free agent at season's end. He'd enjoyed a breakout performance as a superstar the previous season with 87 points and was on his way to matching that total by the end of the '06-'07 campaign.

As recounted by Patrick Hoffman for Sportsnet in 2012, Datsyuk was in contract negotiations with Red Wings management when a midseason rumor emerged claiming he would be traded to the New Jersey Devils for Scott Gomez. At that time, Gomez was also due to become a UFA at season's end and had tallied 84 points the previous season.

According to Hoffman, the trade was so close to taking place that Fox Sports Detroit reported it as nearly a done deal. However, it never happened. Datsyuk would sign a seven-year contract on April 6, 2007, while Gomez departed the Devils on July 1 as a free agent, inking a seven-year deal with the New York Rangers.

Datsyuk tallied back-to-back 97-point performances in 2007-08 and 2008-09 and was a productive member of the Wings for the remainder of his tenure in Motown. Meanwhile, Gomez's point production dropped significantly in the following years with six other clubs and a brief return to the Devils before his retirement in 2016.

During his 18 NHL seasons, Chris Pronger skated for the Hartford Whalers, St. Louis Blues, Edmonton Oilers, Anaheim Ducks and Philadelphia Flyers. However, the Hall-of-Fame defenseman wouldn't have joined the Ducks or Flyers had the Toronto Maple Leafs acquired him in the summer of 2006.

Pronger spent only one season with the Oilers, helping them reach the 2006 Stanley Cup Final. However, he requested a trade that summer, as his wife reportedly didn't like living in Edmonton.

As Gord Stellick recounted for Sportsnet in November 2015, the Maple Leafs were among three teams in the bidding for Pronger, who was born and raised in Dryden, Ontario. Stellick indicated the Oilers would've accepted a package of defenseman Tomas Kaberle, center Alexander Steen and a first-round draft pick.

However, Leafs general manager John Ferguson Jr. was reluctant to part with Kaberle, whom he signed to a five-year contract extension earlier that year. His deal contained a no-trade clause that would begin on July 1. Stellick believed Kaberle would've been livid to be traded before that date only months after re-signing with the Leafs.

Pronger was traded to the Ducks on July 3 in exchange for Joffrey Lupul, Ladislav Smid, two first-round picks and a second-rounder. He'd go on to lead the Ducks to the Stanley Cup the following year. The Leafs, meanwhile, would be mired in a long playoff drought that didn't end until 2013, by which point Kaberle was no longer with them.

The Montreal Canadiens surprised the hockey world in June 2016 by trading defenseman P.K. Subban to the Nashville Predators for blueliner Shea Weber. Subban was in the prime of his career, having won the James Norris Memorial Trophy in 2012-13. Weber, meanwhile, was a well-respected all-around defenseman and former captain of the Predators.

Subban helped the Predators reach the 2017 Stanley Cup Final and became a finalist for the Norris Trophy in 2017-18. After three seasons with the New Jersey Devils, he announced his retirement in September 2022. Weber went on to become captain of the Canadiens and led them to the 2021 Stanley Cup Final before injuries prematurely ended his 16-season career.

Before that trade occurred, the Edmonton Oilers were also interested in Subban. According to TSN's Ryan Rishaug, the Canadiens set a very high asking price that included Leon Draisaitl, the Oilers' first-round pick (fourth overall) in the 2016 Draft, along with either Darnell Nurse or Oscar Klefbom and more.

At the time, those young Oilers were just starting their NHL careers. Draisaitl was coming off a 51-point sophomore season, Klefbom had finished an injury-shortened third season while Nurse had completed his rookie campaign.

Had this deal gone off, it would've significantly altered the futures of both teams. With Draisaitl and Nurse on their roster, the Canadiens likely wouldn't be currently rebuilding their roster. Subban would've provided immediate help to the Oilers, but he wouldn't have had the same effect as Draisaitl, who blossomed into a scoring superstar.

The Oilers wisely decided not to make this move, enabling Draisaitl and Nurse to develop into the core players they are today. That first-round pick, however, didn't work out so well for them as they chose Jesse Puljujarvi, who struggled to play up to expectations during his nearly six seasons in Edmonton.

Chosen first overall by the Tampa Bay Lightning in the 2008 NHL Draft, Steven Stamkos has gone on to become their all-time scoring leader with 525 goals and 1,082 points (and counting). A two-time winner of the Maurice Richard Trophy, he captained them to back-to-back Stanley Cups in 2020 and 2021.

Stamkos' long career with the Lightning, however, never would've happened had a trade taken place during his rookie season that would've sent him to the New York Rangers. In April 2010, the New York Post's Larry Brooks reported that Rangers general manager Glen Sather claimed he had a handshake deal with Lightning co-owner Len Barrie.

Sather told Brooks that he spoke with Barrie when their two clubs opened the 2008-09 season with two games in Prague. By November 2008, the talks turned serious with Barrie being asked to choose two or three players from a wish list that included Ryan Callahan, Brandon Dubinsky and Dan Girardi.

However, the deal fell apart when Barrie ran it by then-Lightning GM Brian Lawton, who wanted no part of it. Co-owner Oren Koules shot it down, and that was the end of it.

It would've been a huge win for the Rangers with Stamkos blossoming into a superstar at the same time that goalie Henrik Lundqvist was entering the prime of his Hall-of-Fame career. Callahan, Dubinsky and Girardi had varying degrees of success in their NHL careers, but nothing that came close to what Stamkos has achieved.

Callahan and Girardi would eventually become Stamkos' teammates in Tampa Bay. Callahan joined the Lightning in 2014 as part of the return for Martin St. Louis. Girardi would follow him three years later, signing with the Bolts as a free agent.

Steve Yzerman is not only the general manager of the Detroit Red Wings, but he was also one of their greatest players. He led them to three Stanley Cups, became their all-time assist leader with 1,063 and sits second to the great Gordie Howe in goals (692) and points (1,755). He also holds their single-season records with 65 goals, 90 assists and 155 points in 1988-89.

Nevertheless, the Ottawa Senators made a serious pitch to the Red Wings for Yzerman in 1995. The Hockey News' Steve Warne recalled that Senators GM Randy Sexton offered up center Alexei Yashin for the Red Wings star.

At the time, Yashin was a rising star who was among the few bright spots on a Senators club that had only come into existence in 1992-93. He had 30 goals and 79 points as a rookie in 1993-94 and 44 points in 47 games during the lockout-shortened 1994-95 campaign.

Yzerman grew up near Ottawa in Nepean. Sexton saw him as someone who could bring in the fans for the Senators, who were struggling on the ice and at the turnstiles.

The Detroit Free Press' Helene St. James recalled Red Wings head coach Scotty Bowman was also the GM with Ken Holland as the assistant GM. Bowman mulled it over but never sought permission from Wings owner Mike Illich to make the deal. However, he did let it be known that Yzerman was available, which didn't sit well with the Wings' long-time captain.

It's a good thing the Red Wings didn't trade Yzerman. His leadership and improved all-around play were crucial to their subsequent three championships in 1997, 1998 and 2002.

Yashin starred for the Senators for five more seasons, including a career-best 94 points in 1998-99. However, he sat out the 1999-2000 season over a contract dispute and was traded to the New York Islanders in June 2001 for a return that included Zdeno Chara and the second-overall pick in 2001 that turned into Jason Spezza.

One of the greatest players in New York Islanders history, Denis Potvin was the foundation on which general manager Bill Torrey built a Stanley Cup dynasty. In his 15-season NHL career, the Hall-of-Fame defenseman captained the Islanders to four straight Cups, won the James Norris Memorial Trophy three times and the Calder Memorial Trophy in 1973-74.

However, the Islanders' history might've turned out very differently had Torrey agreed to trade the No. 1 pick in the 1973 NHL amateur draft to the Montreal Canadiens.

Following Torrey's death in 2018, Sportsnet's Scott Morrison recounted the former Islanders GM many moves that turned the franchise into a powerhouse in the early 1980s. They included drafting Potvin as well as future Hall-of-Famers Bryan Trottier, Mike Bossy and Clark Gilles.

Morrison believed the best move Torrey ever made was not trading that first overall pick in the 1973 draft. Canadiens GM Sam Pollock had a well-earned reputation for fleecing several peers for their first-round picks, the most notable being his machinations that led to the Canadiens selecting Guy Lafleur first overall in 1971.

Pollock reportedly offered Torrey five players from the Canadiens roster in return for that pick. The Isles GM wisely refused and never revealed which players Pollock offered him.

Without Potvin, the Islanders probably wouldn't become a Stanley Cup dynasty. Meanwhile, Canadiens fans are left to daydream over how long their late-1970s dynasty would've lasted with Potvin on a blue line with fellow Hall-of-Famers Larry Robinson, Serge Savard and Guy Lapointe.

Mark Messier and Brett Hull were well-established NHL superstars by 1994. Messier led the New York Rangers that spring to their first Stanley Cup since 1940, adding to the five Cups he won with the Edmonton Oilers. Hull, meanwhile, was already considered one of the greatest goal-scorers in league history. He would go on to win two Cups with Dallas and Detroit.

By July 1994, hard-nosed Rangers head coach Mike Keenan broke his contract with the Rangers to become the head coach and general manager of the Blues. NHL commissioner Gary Bettman brokered a complicated settlement that included Blues forward Petr Nedved being traded to the Rangers as compensation from the Blues.

According to the New York Times, Hull wasn't pleased about the idea of playing for a taskmaster such as Keenan. The high-scoring winger was also hurt to learn that he'd been offered up to the Rangers as compensation before Nedved was eventually shipped to the Big Apple.

Messier, meanwhile, was embroiled in a contract dispute with the Rangers. Rumors grew that he could be shipped to the Blues in exchange for Hull. Keenan thought very highly of Messier, who wanted no less than $5 million per season, which the Blues were willing to pay him.

Despite speculation suggesting a deal was close, it never came to pass. Rangers GM Neil Smith negotiated a new deal for Messier worth $6 million per season. Hull outlasted Keenan in St. Louis as the latter was fired by the Blues in December 1996. Two years later, "The Golden Brett" would sign with the Dallas Stars as a free agent.

The Philadelphia Flyers pulled off one of the biggest trades in NHL history in June 1992 by acquiring the rights to Eric Lindros from the Quebec Nordiques in exchange for Peter Forsberg, Steve Duchesne, Kerry Huffman, Mike Ricci, Ron Hextall, and Chris Simon plus the Flyers' first-round picks in 1993 and 1994 and $15 million in cash.

Lindros went on to become a superstar with the Flyers despite injuries (including several concussions) and clashes with general manager Bob Clarke. Meanwhile, the return received by the Nordiques laid the foundation for what would become a two-time Stanley Cup champion after the club relocated to Colorado in 1995 and became the Avalanche.

However, the New York Rangers also put in a serious bid for Lindros. As The Athletic's Kevin Kurz noted in his August 2022 recollection of the deal, the Nordiques' wily owner Marcel Aubut attempted to get out of his agreement with the Flyers at the last minute in favor of the Rangers' bid.

The Rangers' offer would've sent Tony Amonte, Alexei Kovalev, Doug Weight, John Vanbiesbrouck, three first-round draft picks and $12 million in cash to the Nordiques. Those four players enjoyed long and productive NHL careers, but whether they would've turned the future Avalanche into Stanley Cup champions is debatable.

Having Lindros on the same club as Mark Messier would've given the Rangers a dynamic duo at center. However, what they would've given up to get him might have prevented the Rangers' Cup championship from happening two years later.

It would take arbitration to settle the dispute, with the decision going in favor of the Flyers. It worked out for the best in the short term for the Rangers, as they went on to win the Stanley Cup in 1994. Lindros would suit up for the Rangers seven years later following an August 2001 trade by the Flyers.

The Edmonton Oilers shipping Wayne Gretzky to the Los Angeles Kings in 1988 was the most consequential trade in NHL history. It marked the beginning of the end for the Oilers' Stanley Cup dynasty, turned a spotlight on the Kings that the franchise had never had before, and initiated the league's expansion into the American Sun Belt markets.

However, there was a possibility that Gretzky would've ended up instead with the Vancouver Canucks. During a January 2021 episode of the Sportsnet video series "Hey Burkie", former NHL executive Brian Burke indicated The Great One was close to landing in Vancouver.

In 1988, Burke was the Canucks' director of hockey operations. He was approached by Arthur Griffiths, son of Canucks owner Frank Griffiths, who said he'd received a call from Oilers owner Peter Pocklington offering up Gretzky. In return, Pocklington wanted $25 million in cash, goaltender Kirk McLean, winger Greg Adams and three first-round draft picks.

General manager Pat Quinn asked Burke to crunch the numbers to see if the Canucks could make it happen. Burke said he would've loved to have Gretzky on the Canucks but insisted they couldn't afford to cover the money Pocklington sought. Burke also didn't want to part with McLean and Adams.

Had the Canucks been able to swing the deal, it might've turned them into an NHL powerhouse. They already had the promising McLean on the roster, center Trevor Linden would make his NHL debut in 1988-89 while future superstar winger Pavel Bure joined the club in 1991-92. A line with Gretzky and Bure could've been unstoppable.

However, the growth of hockey in the United States wouldn't have been the same had Gretzky not gone to Los Angeles when he did. The NHL would likely have a much smaller footprint in today's American sports market and certainly wouldn't be on pace to earn a projected $6.2 billion in revenue this season.

Additional info via Hockey-Reference.com.