The NHL is unlike many pro sports leagues. Loyalty is praised; winning a Stanley Cup with the team that drafted or signed you adds extra significance and respect. The narrative of sticking with one team through thick and thin, and eventually achieving the ultimate goal really resonates with the franchise, the fans, and the city itself.
In other leagues, you’ll often see a player leave their original team for higher pay or a better chance to win. That doesn’t mean it doesn’t happen in the NHL; it does, most recently with Brady Tkachuk. However, the emphasis is on winning with the team that originally took a chance on you, especially as the star.
Wayne Gretzky did it with the Edmonton Oilers, Sidney Crosby with Pittsburgh, Jonathan Toews and Patrick Kane with Chicago, and Alex Ovechkin with Washington. For the past decade, it’s seemed like Connor McDavid is on the same path.
History of superstars and the Stanley Cup
For some players, winning takes a long time; for others, it happens almost instantly. Sidney Crosby won a Stanley Cup at 21. He is the youngest captain in NHL history to do so. By age 29, he’d led the Pittsburgh Penguins to two more championships after going back-to-back in 2016 and 2017. It was similar for Wayne Gretzky: he was 23 and 24 for his first two cups and 26 and 27 for the next two, leading the Oilers dynasty in the 1980s. Patrick Kane won a Cup at 21 and had three total by age 27. So these star players have a trend of winning early and often.
However, some guys go their entire career without a cup. It’s become increasingly more common since the expansion era. Even a guy like Steve Yzerman, one of the best players of his generation, went 13 years without a ring. The same could be said about Alex Ovechkin, and right now, Connor McDavid seems to be on a similar career trajectory.
The Oilers’ Stanley Cup window
I’d be comfortable saying Connor McDavid is far and away the most dominant athlete in the big four North American sports right now. I would argue the only comparison is Shohei Ohtani, in that McDavid is so much better than the second-best hockey player in the world that it’s unbelievable. The fact that the Oilers are in year 11 of the McDavid era and are still without a championship is very surprising.
Since McDavid came into the league, he’s been considered the best hockey player in the world. Because of how dominant he’s been throughout his career, it doesn’t seem to be a matter of if McDavid wins—it’s a matter of when. However, after last season’s first-round exit, McDavid called the Oilers “an average team with high expectations.”
The high expectations come with McDavid’s dominance. McDavid is undoubtedly the most skilled player in NHL history, and he’s the best player we’ve seen since Gretzky. From 2022 to 2025, the Oilers were eliminated in the playoffs by the team that went on to win the Stanley Cup, including back-to-back Stanley Cup Final losses.
This pattern ended when the Oilers were eliminated by the Anaheim Ducks in six games. McDavid was point-per-game throughout the series despite not having his biggest advantage, his speed. He played through foot and ankle fractures from Game 2 on.
The biggest question mark for the Oilers over the past decade has been goaltending. They had Cam Talbot, Mikko Koskinen, Mike Smith, Jack Campbell, and Stuart Skinner. None of them were elite by any stretch, but with a guy as dominant as McDavid, that doesn’t necessarily matter. It’s more about coming up clutch when it counts.
Always coming up short
Throughout the McDavid era, the Oilers have only missed the playoffs three times and haven’t since 2019. But until 2022, it didn’t really feel like they could go all the way. After beating L.A. and Calgary, the Oilers reached the Western Conference Final against Colorado. The Avalanche swept them, and Colorado won the Cup.
In 2023, the Oilers faced the Vegas Golden Knights in the second round but lost in six games. The Golden Knights went on to win the Stanley Cup, beating a team the Oilers have become very familiar with.
The closest the Oilers have gotten to a Cup was in 2024; being down 3–0 in the Stanley Cup Final, they came back and forced a Game 7. It was one of the best playoff runs in recent memory. They lost Game 7, ending up one game short of the greatest comeback in hockey history.
After 2024 was the infamous offer sheets of Dylan Holloway and Phillip Broberg. Even with those two losses in their lineup, the Oilers reached the final in 2025, once again taking on Florida. If they had won Game 2 of that series, we’re probably not having this conversation. However, they lost again.
Cementing himself as the GOAT
This season seems to be different. The Oilers are off to an 9–2–2 start. Mind you, this is all without Freddie Andersen. If the past is any indication, he’s the goalie the Oilers have wanted for years. Also, McDavid is playing at a video-game pace. He has 36 points in 13 games. Which is as crazy as it sounds.
If McDavid and the Oilers keep playing at this pace, McDavid could win it all. I’m not thinking just the Stanley Cup, either; right now, McDavid is on pace to have the single greatest individual season in NHL history. I mean, him winning everything! Imagine this: he wins the Hart for MVP and the Ted Lindsay (MVP voted by other players); the Art Ross, and the Richard Trophy, on top of winning the President’s Trophy, Stanley Cup, and the Conn Smythe Trophy. It would be the single greatest season a single player could have.
A season like that is rare and highly unlikely given the skill level of the NHL in its current state. However, if anyone could do it, it’s McDavid. Now would be the time to do it as well, as some media outlets are questioning McDavid’s tenure in Edmonton and question his legacy as well.
Did anyone come close to winning it all?
Wayne Gretzky came close to accomplishing this in 1984–85. Gretzky won the Hart, the Art Ross, the Lester B. Pearson Award (now known as the Ted Lindsay Award), and even though the Rocket Richard Trophy didn’t exist yet, he would’ve gotten it. Gretzky led the NHL with 73 goals. On top of that, the Oilers won the Stanley Cup, and Gretzky was awarded the Conn Smythe Trophy for playoff MVP. However, the Oilers didn’t win the President’s Trophy that year.
Mario Lemieux came close as well. In 1992–93, Lemieux won the Hart, Art Ross, Ted Lindsay, but no Stanley Cup; the Montreal Canadiens won it that year. Also, the most bizarre part is that he didn’t win the Rocket Richard Trophy. Even though Lemieux finished with 69 goals, he didn’t win. Alex Mogilny and rookie Teemu Selanne both scored 76 goals.
In today’s NHL, it’d be borderline impossible for McDavid to match the single-season point totals Gretzky and Lemieux posted. Lemieux’s best season, stats-wise, came in 1988–89 when he had 85 goals and 199 points in only 76 games. Gretzky’s best season was 1985–86, following up his near-perfect award run the year prior with 52 goals and 163 assists for 215 points in 80 games.
They say those are the two greatest seasons in NHL history. However, if McDavid can win it all, including individual awards as well, it will be the single greatest performance ever in one NHL season. If he can pull this off, it may be time to start referring to Connor McDavid as the best hockey player of all time.
In the McDavid era, the Oilers are yet to win a President’s Trophy. Which is fascinating considering McDavid has averaged 1.55 points per game throughout his career. You’d think those stats would have the Oilers steamrolling teams in the regular season, but no!
This is where Babcock comes in
This is where adding Mike Babcock as head coach could make the difference. As a coach, he’s known for bringing fringe playoff teams to the next level. He did it in Detroit in his last few years there. He did it in Toronto, with Auston Matthews and Mitch Marner, who at the time were establishing themselves in the NHL.
Now, with a real contender, Babcock has another chance to take a team to the next level. Even though the Babcock hiring brought some controversy. Mark Messier was openly against it, but it’s amazing how winning fixes everything. With the Oilers off to an 9–2–2 start and Devon Levi seemingly solving the goaltending issue for now, all is right with the world.
Obviously, it’s still very early in the season, and there are a lot of unknowns over an 84-game season. However, this may finally be the time when Connor McDavid and the Edmonton Oilers silence their doubters.
Photo by Curtis Comeau/Icon Sportswire
