Throughout the years, we’ve seen many lucrative free agent signings change the course of NHL history. The Chicago Blackhawks’ signing of Brian Campbell helped them end a 49-year Stanley Cup drought. The Boston Bruins signing of Zdeno Chara made them a class of the NHL.

But some signings have failed to pan out for both parties. A player sees his production go way down, and he’s a public enemy for taking away the team’s money and salary cap space. And then we’ve just seen some teams ditch loyalty and choose the money instead. Oh, and we missed out on seeing some iconic duos dominate the NHL together. Spoiler alert: What if Brett Hull and Wayne Gretzky played together? Two of the top four all-time goals leaders on one line? Yes, please.

There have been times where a player chose the wrong team to sign with. And we can only wonder what could have been. Here’s a look at 15 NHL free agent signings that never happened, but should have (with explained reasons why).

15. Mats Sundin Signs With New York Rangers

via nhl.com

Mats Sundin was one of the greatest NHL players of his time. He’s the Toronto Maple Leafs all-time leading scorer with 420 goals and 987 points. But the way he handled the rest of his career was extremely controversial and questionable.

Firstly, he refused to waive his no trade clause at the 2008 trade deadline, forcing the free-falling Leafs to keep the veteran instead of securing multiple assets for him. Sundin then hit free agency in 2008, and the Vancouver Canucks instantly offered him a two-year deal worth $20 million. He didn’t sign with them until mid-December on a one-year deal.

The Rangers and Canucks were the two teams Sundin narrowed his list down to. Had he signed with the Rangers in the offseason he would have joined a team with fellow Swedes Markus Naslund and Henrik Lundqvist. Perhaps he would have won his only Stanley Cup there, too.

14. Christian Ehrhoff Signs With Detroit Red Wings

Jerome Miron-USA TODAY Sports

Christian Ehrhoff enjoyed a pair of productive seasons with the Vancouver Canucks, scoring 28 goals and 94 points from them over the 2009-10 and 2010-11 seasons. But the Canucks were strapped for cash in the 2011 offseason, and chose to keep Kevin Bieksa while letting Ehrhoff hit free agency.

The Red Wings were a great destination for Ehrhoff, as they lost Brian Rafalski to retirement. Ehrhoff had the chance to join a legitimate contender and play alongside Hall of Famer Nicklas Lidstrom. But he chased the money and signed a 1o-year, $40 million deal with the Buffalo Sabres instead.

Ehrhoff struggled in three seasons with Buffalo, scoring no more than 33 points in a season. He bounced around in the NHL for a while and is now playing overseas in Europe. If he had went to the right place instead of where the money was, he could have been a star in Detroit.

13. Paul Kariya Signs With Vancouver Canucks

via alchetron.com

Paul Kariya was one of the finest superstars during the ’90s and 2000s. The Mighty Ducks of Anaheim captain is fourth all-time in team scoring with 300 goals and 669 points. But Kariya rejected a contract extension with Anaheim after their run to the 2003 Stanley Cup Final, and signed a one-year deal with the Colorado Avalanche worth a bargain $1.2 million.

Hard to blame Kariya for joining a team with the likes of Joe Sakic, Peter Forsberg, Milan Hejduk, Teemu Selanne and Rob Blake. But Kariya also went to free agency in the 2005 offseason, but chose to sign with the Nashville Predators.

The North Vancouver, B.C. native should have opted for a homecoming, and the Canucks should have gone hard after him. Kariya could have been on a line with the Sedins and/or Brendan Morrison and Markus Naslund. Kariya had two solid years in Nashville, but signed with St. Louis where his career faded and he had to retire due to concussion problems.

Perhaps he could have been the missing piece to help them win the Stanley Cup in 2011. Or sooner than that…

12. Jaromir Jagr Signs With Pittsburgh Penguins 

Brace Hemmelgarn-USA TODAY Sports

After three seasons in the KHL, Jaromir Jagr made an epic return to the NHL. There were plenty of interested teams, but he opted to join the Philadelphia Flyers despite many rumors that he would return to the Pittsburgh Penguins. He won a pair of Stanley Cups there in the ’90s and was the franchise’s best player not named Mario Lemieux.

A return to Pittsburgh would have been epic for Jagr. He would have had the chance to play with both Sidney Crosby and Evgeni Malkin, while bringing back an awesome nostalgic feel for hockey fans. Jagr played well in Philadelphia, but has played for five teams since returning to the NHL. Jagr may have a pair of Stanley Cups, but the man has gone 25 years without one – and he deserves another ring.

It would be awesome if Jagr returned to Pittsburgh when he came back to the NHL in 2011. The idea of him getting to tell people he played with both Lemieux and Crosby would be a Hollywood epic.

11. Chris Drury Re-Signs With Buffalo Sabres 

via sportsnet.ca

Chris Drury was a force for the Buffalo Sabres in the 2005-06 and 2006-07 seasons, leading them to the Eastern Conference Final both years. He scored a total of 67 goals and 136 points over those two seasons. However, the Sabres (for some reason), didn’t really push to re-sign him after winning the Presidents’ Trophy in 2007, and allowed him to become a free agent.

Drury signed a five-year contract worth $35.25 million, but became one of the most overpaid and underachieved NHLers in his four seasons with the New York Rangers. Drury had the rest of his contract bought out after the 2010-11 season and never played another NHL game.

The Sabres should have pushed hard to keep Drury, but they’ve yet to win a playoff series since he left. Drury never came close to a 30-goal season, either. This was simply a mutually horrible breakup for both sides. Did I mention the Sabres didn’t keep Daniel Briere either?

10. Zdeno Chara Signs With Ottawa Senators

Geoff Burke-USA TODAY Sports

The 2005-06 Senators were one of the NHL’s best teams. Both Dany Heatley and Daniel Alfredsson posted 103-point seasons, Jason Spezza added 90 and four other players added 20 goals. Dominik Hasek and Ray Emery also combined for 52 wins. Oh, and Zdeno Chara and Wade Redden were among the best blueliners in the NHL. After the Senators lost in the second round of the playoffs to the Buffalo Sabres, the team had to choose between Chara (a pending free agent), and Redden (a free agent in two years).

Ottawa saw Chara sign a five-year deal worth a bargain $37.5 million, where he helped the Bruins become the class of the Eastern Conference for many years – winning the 2011 Stanley Cup and reaching it again in 2013.

The Senators made the Stanley Cup in 2007, but lost to the Anaheim Ducks. They haven’t been relevant since, and Redden signed with the New York Rangers in 2008. Chara was always the better defenceman – Ottawa should have re-signed him while finding a trade partner for Redden.

But the Bruins picked up Chara and made Ottawa pay.

9. Jarome Iginla Re-Signs With Boston Bruins

Sergei Belski-USA TODAY Sports

Jarome Iginla spent over a decade as the Calgary Flames franchise player, scoring 30 goals every season despite having no star centreman to work with. With the Flames entering a rebuilding stage in 2013, he nixed a trade to the Boston Bruins and got dealt to the Pittsburgh Penguins instead.

Fittingly, Boston swept Pittsburgh in the Eastern Conference Final, only to lose to Chicago in the Stanley Cup Final. Iginla then signed a one-year deal with Boston for the 2013-14 season. He scored 30 goals and 61 points, leading the Bruins to the Presidents’ Trophy by a mile. Unfortunately, the Montreal Canadiens upset Boston in the second round. Iginla didn’t want to take a pay cut and took a three-year, $16 million deal from the Colorado Avalanche.

Iginla has seen his stats go way down, while the Avalanche haven’t been close to playoff contention. Iginla will get his final shot at a ring this spring, but Boston would have given him every chance he needed. The Bruins haven’t made the playoffs since he left town, either. Perhaps both parties should have found a way to reunite.

8. Sergei Fedorov Re-Signs With Red Wings

Rick Osentoski-USA TODAY Sports

Though Steve Yzerman, Chris Osgood and Nicklas Lidstrom took most of the attention during the Red Wings dynasty years of the ’90s and 2000s, Sergei Fedorov was no slouch himself. The Hall of Famer scored 400 goals and 954 points during his tenure in Detroit. Fedorov was a member of the 1997, 1998 and 2002 Stanley Cup teams, too.

Fedorov then got greedy and rejected lucrative deals from Detroit, including a five-year offer for $50 million. He then joined Anaheim in the 2003-04 season, scoring 31 goals and 65 points. However, Anaheim was among the worst teams while the Red Wings ran the Presidents’ Trophy.

Fedorov played four more years in the NHL, but was well past his prime by that point. Detroit missed out on more chances at championships (in 2004, 2006 and 2007), while Fedorov saw his career fade quickly. Perhaps he should have taken both the money and the chance to win more championships.

7. Daniel Alfredsson Signs With Boston Bruins

Marc DesRosiers-USA TODAY Sports

The Ottawa Senators were expected to bring back their veteran captain on a one-year deal, but rough negotiations between Bryan Murray and Daniel Alfredsson led to the franchise icon moving on. The Detroit Red Wings and Boston Bruins were the other frontrunners for Alfie’s services, but he wound up signing a one-year deal to play in the Motor City.

Alfredsson was 41 years of age and on his last legs, and Detroit was not a Stanley Cup contender. They barely got into the postseason, where the Bruins made easy work of them in the first round. Alfredsson could have been a difference maker on a loaded Boston team that was one win away from reaching the Eastern Conference Final.

Alfredsson ruined his own chance of retiring as a Stanley Cup champion. It’s a shame, because he really deserved it.

6. Ryan Smyth Re-Signs With Edmonton Oilers

via sportsnet.ca

Long after Wayne Gretzky and Mark Messier left Oil Country, Ryan Smyth emerged as the franchise’s new star. He was four-time 30 goal scorer in Edmonton and was a key part of them reaching the Stanley Cup Final in 2006, before falling to the Carolina Hurricanes in seven games.

Smyth was having another strong season in 2007, scoring 31 goals and 53 points. The Oilers looked destined to reach the playoffs again, but they were unable to reach a new deal. Edmonton traded him to the New York Islanders, ensuring they got future assets (though none of them panned out). Smyth then played with the Colorado Avalanche and Los Angeles Kings, before returning to Edmonton in his final three years (when he was clearly past his prime).

Smyth never won a Stanley Cup, and the Oilers haven’t made the playoffs since 2006. Perhaps re-signing Smyth back in 2007 would have kept them a playoff contender. But he struggled once he left the team, and Edmonton didn’t find their replacement until Connor McDavid in the 2015 Entry Draft.

5. Brad Richards Signs With Toronto Maple Leafs

Charles LeClaire-USA TODAY Sports

Brad Richards was a superstar on the Tampa Bay Lightning, and was the centrepiece of their 2004 Stanley Cup winning team. However, the Lightning were among the NHL’s worst teams in 2008, and they dealt him to the Dallas Stars. Richards had plenty of success there, posting a 91-point season in 2009-10 and a 77-point campaign the following year.

When Richards hit free agency, the Toronto Maple Leafs and New York Rangers were his primary destinations. Ultimately, he signed with the Rangers for $60 million over nine years. Richards struggled in his three seasons there and was bought out after the 2013-14 season.

The Leafs could have been a lot better with Richards. They would have gone on a deeper playoff run in 2013 and could have made it in 2014 and 2015 with his stardom. He simply wasn’t a good fit under John Tortorella. For Richards’ sake, his career wouldn’t have dwindled so quickly if he had Phil Kessel on his line.

That would have been one combination for the ages, but Richards took the money instead.

4. Peter Forsberg Signs With Vancouver Canucks

Ron Chenoy-USA TODAY Sports

Peter Forsberg was a two-time Stanley Cup champion with the Colorado Avalanche and won both the Art Ross and Hart Trophy in 2003 – finishing with 29 goals and 106 points. But with the salary cap coming into play for the 2005-06 season (after the lockout), Colorado couldn’t afford to keep both him and Rob Blake.

Forsberg was rumored to possibly join the Toronto Maple Leafs or Vancouver Canucks, who each had a fellow Swedish star (Mats Sundin and Markus Naslund, respectively). Forsberg ultimately ended up joining the Philadelphia Flyers on a two-year deal worth $11.5 million. He missed 22 games in 2005-06, and then was traded to the Nashville Predators near the 2007 trade deadline (he missed 25 games that season). Forsberg played briefly with Colorado in 2007-08 and 2010-11 before hanging up his skates for good.

So as you could see, the man was never able to stay healthy. On top of that, wouldn’t he, Naslund and the Sedins make for a dominant top-four? The Canucks could have given him the money, and Forsberg could have been a key piece in a championship run. He stuck it out in Philly, not knowing it was the path of a fading career that saw too many injuries take place on his body, too.

3. Brett Hull Re-Signs With Dallas Stars

via sportsdays.dallasnews.com

The Dallas Stars were as dominant as the Avalanche and Red Wings from 1996-2006. The only difference is they won just one Stanley Cup, compared to a pair for Colorado and three for Detroit during that time frame.

Well, it’s no coincidence. The 1999 Stanley Cup Champion Stars had Ed Belfour, Joe Nieuwendyk, Mike Modano and Brett Hull. The Golden Brett scored 32 goals and 58 points in the 1998-99 season, while also scoring the memorable Stanley Cup-winning goal in Game 6.

Dallas didn’t pick up the option on his contract for the 2001-02 season, and he wound up signing with the Detroit Red Wings. Hull won a Stanley Cup that year, while the Stars missed the playoffs. Hull’s Red Wings remained a powerhouse in 2003 and 2004, while the Stars one just a single playoff series over those two seasons.

Perhaps they should have kept a franchise player. Instead, he went to one of their rivals and won a Stanley Cup with them. Not a good idea to let go the man who’s fourth all-time in goals.

2. Mark Messier Re-Signs With New York Rangers

Joshua Dahl-USA TODAY Sports

Though most of Mark Messier’s legacy remains with the Edmonton Oilers, he was a huge part of the New York Rangers resurgence in the ’90s. He helped them win the Stanley Cup in 1994 – their first title in 54 years.

As the Rangers transitioned into a rebuilding stage for the 1996-97 season, Messier expressed his desire to stay with the team and was willing to take a massive pay cut. However, GM Neil Smith had Wayne Gretzky (more on this later), and Pat LaFontaine as his centres, and was content with them. Messier signed a three-year, $20 million deal with the Vancouver Canucks. He didn’t do much of anything, he took the captaincy from Trevor Linden and sued them over a decade later in an arbitration case to earn more money.

The Rangers took years to become relevant again after Messier left. They should have just paired Messier with the great Gretzky one more time. It could have led to another championship for the Rangers.

1. Wayne Gretzky Re-Signs With St. Louis Blues

Kirby Lee-USA TODAY Sports

What else is there to say about The Great One? The greatest NHL player to ever win won four Stanley Cups and his 894 career goals and 2,857 career points will never be touched. Wayne Gretzky kickstarted the Edmonton Oilers dynasty, then spent seven-and-a-half seasons with the Los Angeles Kings, turning them into a powerhouse after years of irrelevance.

Gretzky was traded to the St. Louis Blues during the 1995-96 season, where they lost to the Detroit Red Wings in a classic seven game series in the second round of the playoffs. Gretzky scored eight goals and 21 points in just 18 games.

The Blues tried bringing him back on a three-year, $15 million deal. Gretzky instead played his final three seasons with the Rangers. They missed the playoffs in both 1998 and 1999. Gretzky could have stayed in St. Louis and played with Brett Hull, while possibly adding another championship. Instead, we saw The Great One finish his career on a lackluster team.

 

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