Loyalty can be hard for hockey fans to understand.

It’s easy for us to wonder how some superstars can remain so loyal and dedicated to playing for one team without the chance to succeed more and win more elsewhere. But we don’t understand the feeling of being drafted and developed into a superstar by one team. We don’t always understand that a player loves the city and it’s convenient for their family. Just because a player isn’t on a winning team, doesn’t mean he’s not loving it there.

On the other hand, some NHL legends knew when it was time to cut ties with loyalty and pursue a championship.

Here is a look at eight NHL players who had the golden chance to join a Stanley Cup winning team that never (or have yet to), captured the glory. Also, we’ll look at eight NHL veterans who capitalized on the chance to join a contender that got rewarded with a championship.

15. Missed Out: Daniel And Henrik Sedin

Ron Chenoy-USA TODAY Sports

I’ll start off by saying that the Sedin twins have not been in primary position to be traded to a Stanley Cup contender. The twins have made it very clear they’d like to finish their careers in Vancouver, and the front office has never seriously tried to trade them. Because of their loyalty, the Sedins will probably never win a championship.

They were free agent on July 1, 2009. There were rumors the Canucks would pursue other stars if they didn’t bring in the Sedins, but general manager Mike Gillis went to Sweden to negotiate and come to a deal with them.

Thing is, the Sedins could have probably picked their home, assuming they were willing to take pay cuts. Over the past three years, they could have easily asked for a trade to a contender, but it appears that they value loyalty over championships. Whatever makes them happy?

14. Won It: Kimmo Timonen

via secondcityhockey.com

Kimmo Timonen is one of the most underrated defencemen in recent memory. The four-time All-Star was a standout on both the Nashville Predators and Philadelphia Flyers for many years. In his prime, Timonen could shut down the league’s best forwards and put up 40-50 point seasons like there was no tomorrow.

But after six productive seasons with the Flyers, Timonen missed most of 2014-15 after doctors found blood clots in his lungs and right leg. Wanting to win a Cup before retirement, the Philadelphia Flyers traded the perennial star to the Chicago Blackhawks for a pair of draft picks.

Timonen played 16 games with the Blackhawks and played 18 playoff games with them, as Chicago won its third Stanley Cup since 2010. Winning the title again wasn’t that unique, but it was special to see Timonen retire a champion after such an emotional battle for his career and life. The timing for the trade worked out perfectly.

13. Missed Out: Ryan Smyth

via thecomeback.com/

For Ryan Smyth, timing was everything. He always knew when to go to the front of the net, cause havoc and score goals. But when it came to changing teams, Smyth didn’t always pick the correct time.

The Edmonton Oilers traded him a year after reaching the Stanley Cup Final at the 2007 trade deadline to the New York Islanders. The Oilers were in the playoff race at the time of the trade but unraveled, while Smyth’s Isles were one-and-done in the postseason. Smyth then signed a two-year deal with the Colorado Avalanche, but even the great Joe Sakic couldn’t win a Cup with him there.

Smyth then spent two seasons with the Los Angeles Kings, then requested a trade back to Edmonton in the 2011 offseason. Figuratively, Los Angeles won the Cup in 2012. Smyth also chose to play his final season (2013-14), with Edmonton. Los Angeles won the Cup again in 2014.

You have to credit Smyth’s loyalty, but it would have been nice to see Captain Canada become Captain Stanley Cup champion.

12. Won It: Marian Hossa

Bob DeChiara-USA TODAY Sports

It took a long time, but Marian Hossa is another example that third time’s a charm.

Hossa was in his third season with the struggling Atlanta Thrashers and got traded to the Pittsburgh Penguins at the 2008 trade deadline. The Pens lost to the Detroit Red Wings in the 2008 Stanley Cup Final. Hossa then went to Detroit the following season, only for Pittsburgh to avenge its loss by capturing the title in 2009.

Hossa had rejected an extension from Pittsburgh and Detroit’s cap space prevented them from being able to keep him in 2009. Hossa then signed a 12-year deal worth $62.8 million. Eight years later, he’s a three-time Stanley Cup champion, part of the 500 goal-club and has well over 1,000 points.

It took longer than it should have, but Hossa finally won the well-deserved Stanley Cup three times.

11. Missed Out: Paul Kariya

via alchetron.com

The Mighty Ducks of Anaheim were an expansion team in the early ’90s, and Paul Kariya became the franchise star to build around. He scored 300 goals and 669 points in his time there — fourth most in franchise history. Kariya’s explosive speed and beautiful shot made him one of the league’s most dominant forwards.

However, Kariya made a surprising decision to leave Anaheim after losing Game 7 of the 2003 Stanley Cup Final. Kariya took an $8.2 million pay cut to join the Colorado Avalanche with old friend, Teemu Selanne. Both veterans struggled and the Avalanche were eliminated in the second round.

Kariya should have stayed loyal to the Ducks, because they ended up winning the Stanley Cup in 2007. But his ugly departure from Colorado was the last straw in the relationship with the team that drafted him. And as sad as it is, Kariya paid the price by never winning a Stanley Cup.

10. Won It: Luc Robitaille

via thescore.com

The highest-scoring left winger in NHL history (668 goals, 1,394), spent the bulk of his career with the Los Angeles Kings. LucRobitaille put up at least 40 goals (and one 63-goal season), from 1986-87 to 1993-94. Robitaille’s Kings weren’t all that great until Wayne Gretzky joined them, however.

Robitaille spent time with the Pittsburgh Penguins, New York Rangers and Kings again, before going to the Detroit Red Wings in 2001-02 with the hopes of winning a Stanley Cup. He did his due in scoring 30 goals and 50 points while adding 10 playoff points. Detroit won the Stanley Cup in 2002 — it’s third title in six years.

He played one more year in Detroit before spending his last two years with the Kings. Robitaille was committed to the Kings for most of his career, but he was rewarded when he finally realized his best chance at a Cup was somewhere other than the West Coast.

9: Missed Out: Ilya Kovalchuk

via letsgoleafs.com

Ilya Kovalchuk was one of the NHL’s most dynamic scorers during his career. He scored 29 goals in his rookie 2001-02 season, then scored 38 and 41 over the next two seasons. After the lockout, Kovalchuk only got better. He scored 52 goals in 2005-06, 42 in 2006-07 and 52 again in 2007-08. He would reach the 30-goal mark over the next four seasons as well.

But Kovalchuk surprised many by retiring after the 2012-13 season — just one year after the New Jersey Devils fell two games short of winning the Stanley Cup. Kovalchuk retired to join the KHL, leaving $77 million on the table.

He retired while in his prime and could have been part of a currently promising New Jersey team, led by Taylor Hall and Cory Schneider. Better yet, he could have left the Atlanta Thrashers years earlier and won a Cup elsewhere. But it does look like he’s never going to find his name on a Stanley Cup.

8. Won It: Chris Pronger

via thestar.com

Few blueliners accomplished so much and dominated so consistently like Chris Pronger. He won two Olympic gold medals with Team Canada, both the Norris and Hart Trophy in 2000 and won the Stanley Cup with the Anaheim Ducks in 2007. For Pronger, patience and persistence paid off.

With the St. Louis Blues entering a rebuild, the Edmonton Oilers signed him to a five-year deal worth $31.25 million. Edmonton fell just one game short of winning the first Stanley Cup, and Pronger surprisingly requested a trade. He went to Anaheim and formed a dangerous pairing with Scott Niedermayer.

Those two shut down the NHL’s top forwards throughout the playoffs, including Daniel Alfredsson — Jason Spezza — Dany Heatley of the Ottawa Senators in the Stanley Cup Final. Pronger knew when it was time to ask for a trade and won a championship. Don’t believe he’ll be complaining.

7. Missed Out: Curtis Joseph

via sportsnet.ca

Curtis Joseph is one of the greatest undrafted NHL players of all-time. The long-time St. Louis Blues, Edmonton Oilers and Toronto Maple Leafs standout posted seven 30-win seasons. CuJo won 454 games and posted 90 shutouts in a career that lasted nearly two full decades.

Though he never won a Vezina Trophy, he was a runner-up in three different seasons. Joseph was also part of Team Canada’s gold medal-winning team at the 2002 Winter Olympics. Despite all of those accomplishments, Joseph never won a Stanley Cup nor reached the Final in his career.

Joseph joined the Edmonton Oilers in 1995-96 in a trade, which is a shame because the Blues were Cup contenders at the time. He spent four seasons with the Leafs, who made the playoffs each of those years but didn’t go to the Final. Joseph also spent two years in Detroit but couldn’t win a Cup there.

Rather than chase championship rings, he spent two seasons with the Coyotes after the lockout, went to the Calgary Flames for one year then spent his final season on the rebuilding Maple Leafs. He was more about playing what was best for him than winning titles.

6. Won It: Teemu Selanne

via thestar.com

It’s hard to believe how a man with 684 career goals and 1,457 points changed teams so much. Teemu Selanne spent his first four seasons with the Winnipeg Jets before spending six seasons with the Mighty Ducks of Anaheim, where he had a pair of 100-point seasons (and two other seasons of reaching 80 points), in his original stint with them.

Selanne then spent three seasons with the San Jose Sharks before going to the Colorado Avalanche in 2003-04, reuniting with former Anaheim teammate Paul Kariya. After the lockout, Selanne opted to return to the Ducks, who had acquired future Hall of Famer Scott Niedermayer on defence.

The decision to return paid off for Selanne, scoring 88 goals and 184 points in his first two seasons back with Anaheim. Selanne helped the Ducks win the Stanley Cup in 2007, scoring 15 points in the playoffs.

He’d finish his career in Anaheim, and it turned out to be a wise decision as the 36-year-old finally won the Stanley Cup, the one thing he missed on an otherwise illustrious career.

5. Missed It: Jarome Iginla?

Isaiah J. Downing-USA TODAY Sports

Jarome Iginla is 39-years-old and experiencing the worst season of his career, but that’s expected from 39-year-old power forwards who have played two decades in the NHL. Iginla has been one of the league’s best goal-scorers of this era, but this is likely his last chance to win a Stanley Cup. That’s because he was too loyal to the Calgary Flames for too long, then seemed to make the wrong decisions…

Iginla’s part of the 600-goal club, is nearing 1,300 career points, has two Olympic gold medals and two ‘Rocket’ Richard Trophies to his name. It wasn’t until the 2012-13 season where he finally accepted a trade. He was set to go to the Boston Bruins, before waiving it and asking to be dealt to the Pittsburgh Penguins instead.

And it just so happened Pittsburgh and Boston met in the 2013 Eastern Conference Final, with Iginla’s Pens being swept. He then joined Boston the following year, only for the Presidents’ Trophy winners to be sent home in the second round by the Montreal Canadiens.

Iginla could have returned to Boston, but chose to take more money from the Colorado Avalanche, who wasted his 2014-15 and 2015-16 campaigns. Iginla probably should have stayed with Pittsburgh or Boston long-term, but chose the dollars. Here’s hoping he can go out a champion.

4. Won It: Brett Hull

via sportsday.dallasnews.com

Brett Hull began his career with the Calgary Flames, but the team traded him to the St. Louis Blues a year before they won their first and only Stanley Cup to date in 1989. Hull became a superstar in St. Louis, turning them into a perennial Stanley Cup contender. He holds the franchise record in goals (527), and is second in points (36).  He led the league in goals for the 1989-90, 1990-91 (winning the Hart Trophy), and 1991-92 seasons.

But Hull opted to join the Dallas Stars for the 1998-99 seasons, and it became one of the smartest decisions an athlete ever made. He scored the Stanley Cup-winning goal in Game 6 of the 1999 Final (in overtime), that forever enshrined him in hockey history.

Hull would later join the Detroit Red Wings, winning another Stanley Cup with them in 2002. Hull was great in St. Louis, but his willingness to try other teams led to a pair of championship rings.

2. Missed It: Daniel Alfredsson

via alchetron.com

Being the Ottawa Senators captain from 1999-2013 and being the franchise’s all-time leader in goals and points, it’s easy to believe why Daniel Alfredsson played all but his final season in the nation’s capital. However, Alfredsson did have three chances of chasing a Stanley Cup, but didn’t really take any of them seriously.

In both the 2009 and 2011 seasons, the Senators were a mess and could have looked to trade Alfredsson at the deadline, but he wanted to stay and help them rebuild. After the 2013 season, he and general manager Bryan Murray had problematic contract negotiations. With rumors that Alfredsson could join the defending East champion Boston Bruins, all seemed to make sense for him to take a run at the Cup.

But Alfredsson chose to join the Detroit Red Wings, who were not a Stanley Cup contender. They barely qualified for the eighth seed and Boston sent them home in the first round.

If the Bruins had Alfredsson on that 2013-14 team, Alfie could have been the difference in winning a championship. Better yet, he could have asked Ottawa for a trade to a contender while they rebuilt.

2. Won It: Dominik Hasek

via thescore.com

Some believe Dominik Hasek is the greatest goalie to ever live. He didn’t have the most wins, shutouts or Stanley Cup rings, but no goalie could ever make so many saves and steal games the way Hasek did. He single-handedly carried the Buffalo Sabres in the ’90s, winning the Hart Trophy in 1997 and 1998 while winning six Vezina Trophies and three William M. Jennings awards.

But as the Sabres continued to struggle despite Hasek’s brilliance, he joined the Detroit Red Wings in the 2001-02 season. As a 37-year-old, he won a career-high 41 games in the regular season and helped Detroit win its 10th Stanley Cup championship.

Hasek spent most of his prime years with the Buffalo Sabres, but made the wise decision to join a real Cup contender. He retired after his first championship, came back two years later and eventually won another Cup in Detroit before retiring in 2008. The Dominator truly deserved the championships, considering how loyal he was to Buffalo all that time.

1. Missed It: Mats Sundin

via peoples.ru

The first-overall selection in 1989 became arguably the greatest European NHLer of all-time. Mats Sundin leads the historic Toronto Maple Leafs franchise in goals and points, with 420 and 987, respectively. Sundin spent his first four seasons with the Quebec Nordiques before getting traded to the Maple Leafs in 1994.

Even though Sundin’s Leafs consistently made the playoffs (and the Eastern Conference Final in 1999 and 2002), they weren’t good enough to win the Stanley Cup. The Leafs missed the playoffs in 2006, 2007 and 2008. In his final year as a Leaf, Sundin was in a contract year and expected to be dealt to a contender at the trade deadline. TSN’s Darren Dreger reported that top teams such as Detroit and Montreal were interested in his services. But Sundin refused to accept a trade and finished the season in Toronto. He then joined the Vancouver Canucks halfway through the 2008-09 season, though he could have been more impacting if he joined them at the start.

If Sundin just accepted a trade to Detroit for 3.5 short months, he would have been a Stanley Cup champion, but he was too loyal to Toronto.

1. Won It: Ray Bourque

via NHL.com

Ray Bourque isn’t recognized the way Bobby Orr and Nicklas Lidstrom were, but he is the all-time leader among defencemen in goals, assists and points (410, 1,169 and 1,579). Bourque was drafted by the Boston Bruins in the 1979 Draft, and became one of the league’s best all-around players.

From 1979 to 1996, Bourque’s Bruins qualified for the playoffs every year, but weren’t able to win a Stanley Cup. As the Bruins entered a rebuilding stage, Bourque finally asked for a trade to a contender. He joined the Colorado Avalanche in 2000, but they fell one game short of reaching the Final.

Bourque opted to play the 2000-01 season, his final year in the NHL. Colorado beat New Jersey in a thrilling seven-game series to win the Stanley Cup. Though Gary Bettman handed the Trophy over to captain Joe Sakic, the Avs’ star passed it right over to Bourque, who inspired perhaps the most emotional and spine-tingling moment in NHL history.

The great Ray Bourque retired a champion.

 

  • Ad Free Browsing
  • Over 10,000 Videos!
  • All in 1 Access
  • Join For Free!
GO PREMIUM WITH THESPORTSTER
Go Premium!

Videos