Penguins’ Sidney Crosby is a bad omen for Oilers’ Connor McDavid originally appeared on The Sporting News.
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Connor McDavid still hasn’t won a Stanley Cup. The Edmonton Oilers‘ season ended on Thursday night in the first round, well short of their last two seasons, when they lost in the championship series to the Florida Panthers.
By this point in Sidney Crosby’s career with the Pittsburgh Penguins, he had won the Stanley Cup three times. But this isn’t to say McDavid is an underachiever. This is to point out a bad omen.
Crosby won his last Stanley Cup at age 29.
McDavid is 29 now. He’ll turn 30 in January.
A bunch of the all-time greats have failed to win a Stanley Cup after turning 30 years old. Alex Ovechkin, who won at 32, is the main exception.
The Athletic’s Josh Yohe shared this list that emphasizes the point:
Connor McDavid will be in his 30’s the next time he plays in the playoffs.
A list of the best players ever and their ages when they last won a Cup:Gordie Howe, 27
Bobby Orr, 24
Wayne Gretzky, 27
Mario Lemieux, 26
Sidney Crosby, 29
Alex Ovechkin, 32
Jaromir Jagr, 20
McDavid?— Josh Yohe (@JoshYohe_PGH) May 1, 2026
That’s a who’s who of the best hockey players to ever grace the ice. And none of them besides Ovechkin won at the age McDavid will be by next season’s playoffs.
That’s not to say he can’t be the exception. Clearly, McDavid is still an incredible talent.
But the Oilers haven’t maximized his prime window, and now it’s not clear where they might go from here.
They’ll have to solve goalie, and improve the defense, and maybe get more firepower further down the forward depth chart, too. Where are they gonna get the money to do all that?
The reality is that McDavid is now facing an uphill climb toward a Stanley Cup. History isn’t on his side.