Joe Thornton Sharks, Bruins
As the first overall pick in the 1997 draft, Joe Thornton faced hefty expectations to succeed in the NHL. Yet, despite playing in a grand total of 22 seasons, Thornton hasn’t won a single Stanley Cup Finals. It's not that he played on bad teams - in fact, Thornton has made the playoffs 17 times. To go along with that, Thornton has been able to play alongside great talent, such as Evgeni Nabokov, Patrick Marleau, Joe Pavelski, and Brent Burns. Throughout his long career, Thornton has racked up numerous accolades and is currently 9th in all-time assists and 15th in all-time points. But one accolade Thornton hasn’t won yet is a Stanley Cup. While it has been 22 seasons, there is still time for Joe Thornton. Hopefully injuries don't end his career, because he is still getting points and the Sharks have a good roster that can go all the way.
Patrick Marleau Maple Leafs, Sharks
Patrick Marleau’s case shares similarities with Joe Thornton's. He was picked subsequently after Thornton in the 1997 draft, and like Thornton, Marleau is in his 22nd season in the NHL. And similar to Thornton, Marleau hasn’t won a Stanley Cup yet. Throughout his career, he has accumulated over a 1000 points and has scored against all 31 NHL teams (the first to do so). He has also had his chances to win it all - making the playoffs in almost every year of his career. However, the Marleau's only Stanley Cup Finals appearance ended in a loss to the Penguins. In present day, Marleau is declining fast and will need to find a way to win it all soon. The good thing is that he is on a Cup contender with the Maple Leafs.
Henrik Lundqvist Rangers
Somehow, some way, the European goalie with the most wins has never won a Cup. Henrik Lundqvist has proved to be an amazing playoff performer, but the team in front of him has never been great. He has made the Stanley Cup Finals once in 2014, but lost to the Kings. His next closest bids have resulted in two losses in the Conference Finals. If he still wants a Stanley Cup, Lundqvist should request a trade to a contender because the Rangers aren’t currently in a position to win it all. However, Lundqvist has played with the Rangers for the entirety of his career and will most likely stay loyal to his team. Even though the Rangers are rebuilding right now, in two or three years they might be able to make one more run with Hank in the net. However, there are only two years left on Lundqvist’s contract and age is not on his side.
Roberto Luongo Panthers, Canucks, Islanders
Roberto Luongo is the 4th most winningest goalie in the NHL, yet has not won a cup. He was one game away from winning it all in 2011. Unfortunately, the Canucks succumbed to the Bruins in 7 games. Some of his lack of success comes down to “what-if” scenarios. Imagine if he stayed with Zdeno Chara and the Islanders. Then imagine if the Islanders selected a good player with the first overall pick in the 2000 Draft - such as Dany Heatley. Even in reality, Luongo has had his chances. On the Canucks, he played with stars Daniel and Henrik Sedin. And despite making the playoffs six out of seven seasons with Vancouver, Roberto Luongo couldn’t win anything. Now, Luongo is on his second stint with the Panthers and I can't see him winning the coveted Stanley Cup because he is 39 years old. With is first stint with the Panthers, he never made the playoffs from 2001 to 2006. And in his second stint with Florida, from 2014 to now, he has only made the playoffs once. His best chance was with the Canucks from 2009- 2013, but that never came to fruition.
Pekka Rinne Nashville Predators
Pekka Rinne wasn’t a sought-after commodity in the draft. He was an 8th round pick - back when there was an 8th round. He has only made it to the Stanley Cup Finals once in 2017, but that effort resulted in a six game loss. Rinne’s kryptonite has always been the team around him. While the Predators haven’t been consistently terrible, they have been consistently a 1st or 2nd round exit. However, Rinne has always had a great defensive core in front of him. He has played behind great defenders, such as Shea Weber and Ryan Suter. Currently, he is playing with P. K. Subban and Roman Josi - forming the the best defense in the NHL. Because of that, I think Pekka Rinne and his team still can win a Stanley Cup. Last year he fell apart in the playoffs, but in the 2017 playoffs, he played out of his mind.
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