Widely considered the best player of his generation—and maybe even one of the greatest in NHL history—the Edmonton Oilers Connor McDavid has already done nearly everything an NHL superstar can do. He’s won MVPs, dominated scoring races, and delivered highlight-reel plays night after night. He even won the Conn Smythe Trophy last season, even though his Oilers lost in Game 7 to the Florida Panthers.
But without a Stanley Cup, his legacy remains unfinished. And this postseason, as he leads the Oilers into the Final, the narrative around him hangs in the balance. Could this be the moment that tips his career from “great” to “all-time great”? Or will he join the long list of legends who never quite reached the summit by winning Lord Stanley’s Cup?
Stars Who Finally Broke Through to a Stanley Cup
The pressure to win doesn’t always go unfulfilled. Some great players spend years chasing the Stanley Cup before finally breaking through—and when they do, the narrative around their careers transforms almost instantly.
Alex Ovechkin is the most famous recent example. For over a decade, critics questioned whether he was a playoff performer. He scored goals in bunches, won MVPs, and carried the Capitals to regular-season dominance—but the early exits piled up. When he finally lifted the Cup in 2018, everything changed. His career was suddenly “complete,” and the joy of that moment remains one of hockey’s most memorable.
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Steven Stamkos faced a similar path. He spent years leading a talented Tampa Bay Lightning team that always seemed to fall short. A trip to the 2015 Final ended in heartbreak, and questions about the team’s mental toughness began to grow. Then, in 2020 and 2021, everything clicked. Stamkos got his Stanley Cup win—and another.
Ray Bourque, one of the greatest defensemen of all time, finally won the Cup in his very last NHL game. After two decades in Boston without a title, he was traded to Colorado and lifted the Cup in 2001 at age 40. It remains one of the most emotional images in hockey history. His partner in the photo below – Joe Sakic – won two Cups as a player (1996 and 2001) and in 2022 was the team’s general manager when the Avalanche won again.
These players are proof that sometimes, the window doesn’t close. But it takes the right mix of timing, teammates, and maybe even luck.
NHL Stars Who Never Made It: Legends Without a Ring
And then there are the others—players who had all the talent in the world, put up huge numbers, hung in the chase for a long time, and even changed the way the game was played. But they never won the Stanley Cup.
Marcel Dionne is one of the most prolific scorers in NHL history. He ranks sixth all-time in points, ahead of names like Mario Lemieux and Steve Yzerman. But he spent most of his career with the Kings in an era when playoff success was elusive in Los Angeles.
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Mats Sundin was the face of the Toronto Maple Leafs for over a decade. He had the size, skill, and leadership qualities that teams crave. But despite his best efforts, he never made it past the conference final, and the Maple Leafs’ long Cup drought only added to the weight he carried.
Speaking of Maple Leafs who never won the Cup, Patrick Marleau is the NHL’s leader in games played and Joe Thornton was a generational passer and a dominant force for years in San Jose. Both made the Stanley Cup Final in 2016, but that Sharks team ran into the Penguins at the peak of their dynasty. Additionally, both Marleau and Thornton kept chasing the Stanley Cup into their 40s, but it never came.
Goaltenders, too, are haunted by the lack of a championship. Henrik Lundqvist gave the Rangers lots of great games. A Vezina winner, a franchise cornerstone, and a playoff warrior—he led New York to the 2014 Cup Final but fell short (when a goalie interference play wasn’t called of all things). Despite all his brilliance, he retired without a Cup.
These players aren’t failures. They’re legends. They came close, but they serve as reminders that in hockey, even greatness might get you close but isn’t always enough to lift you over the top.
What’s at Stake for McDavid?
McDavid is still young enough to believe his time will come. And based on the level he’s playing at, there’s every reason to believe it could come soon—and more than once. But nothing is guaranteed. Injuries happen. Teams change. The league evolves. The point? Opportunity doesn’t last forever.
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What’s clear is this: if McDavid and his Oilers do win a Stanley Cup, the perception of his legacy will change overnight. He’ll go from being one of the greats to being one of the greatest. He’ll be like Ovechkin, whose 2018 championship with the Capitals rewrote his narrative instantly. Beating Wayne Gretzky’s goal-scoring record hasn’t hurt, either.
For now, McDavid remains in that liminal space. He’s already historic, but still chasing the moment that would cement his name forever. He’s not alone, but he stands out. And as this postseason unfolds, he gets one more chance to escape the fate that befell so many legends before him.
