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The futures of Connor McDavid, Sidney Crosby and Alex Ovechkin will be determined in the coming months
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Published Oct 06, 2025 • Last updated 9 minutes ago • 8 minute read
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Connor McDavid (97) takes part in Edmonton Oilers 2025 training camp at Rogers Place, in Edmonton Thursday Sept. 18, 2025. David Bloom Photo by David Bloom /PostmediaArticle content
With the 109th season of the National Hockey League upon us with three games on Tuesday night, we delve into some burning questions heading into the 2025-26 regular season.
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What’s to make of the fact Connor McDavid hasn’t signed yet?
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There’s no bigger question in the NHL: What does the future hold for the best player in the game, Edmonton Oilers captain Connor McDavid?
Can McDavid’s future be anything but an extension with the Oilers, even though the majority of the hockey world figured it would have been done by now?
We’re in the camp that thinks McDavid and the Oilers will get something done. Whether it’s a shorter term contract for two or three years, or a long-term deal, remains to be determined.
The contract extension signed by Minnesota Wild star Kirill Kaprizov last week — eight years and $136 million US for a record average annual value of $17 million — won’t have any bearing on what McDavid does. Whether McDavid signs for more or less will be determined by the player.
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As for the nuclear option, that McDavid doesn’t sign and is an unrestricted free agent next summer, 31 other general managers across the league should do all they can to clear their respective decks. That’s if Maple Leafs GM Brad Treliving can’t find a way to make it work. We think he would.
Sidney Crosby #87 of the Pittsburgh Penguins celebrates with teammates on the bench after scoring a goal in the second period during the game against the Columbus Blue Jackets at PPG PAINTS Arena on September 27, 2025 in Pittsburgh, Pennsylvania. Photo by Justin Berl /Getty Images North America
Will Sidney Crosby really endure another losing season in Pittsburgh?
Sidney Crosby has 201 points in 180 career Stanley Cup playoff games and has lifted the silver mug three times with the Pittsburgh Penguins.
The Penguins’ prolific captain, however, has not participated in the postseason since 2022 and has not been past the first round since 2018.
And the Penguins head into 2025-26 with as much hope for a playoff spot next April as your Monday night beer-league team: None.
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Crosby’s competitive nature has helped set him apart during his 20-year career. Age has had no chance of catching up to him, as he’s riding a string of three consecutive seasons of 90-plus points.
Crosby wants to finish his career with the Penguins. We’ll see if his thinking has changed in the days leading up to the NHL trade deadline in March, when it’s bound to be clear that Pittsburgh again won’t be participating in the Stanley Cup tournament.
While the Montreal Canadiens have been part of the speculation if Crosby agrees to be moved, wouldn’t his good pal, Nathan MacKinnon of the Colorado Avalanche, try to make a strong pitch?
How will injuries impact the Florida Panthers’ quest for a third consecutive Cup?
The Panthers already had taken a hit with the news that Matthew Tkachuk, a heartbeat-type player if there ever was one, will be out until December because of a lower-body injury.
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Then came the crushing blow regarding captain Aleksander Barkov, who will be out for seven to nine months after he suffered a knee injury during camp. Needless to say, Finland’s desire of earning a medal at the Winter Olympics in men’s hockey is in doubt with Barkov out.
This is where the Panthers’ Cup experience should help, to a degree. We’re not suggesting Barkov is replaceable. Tkachuk isn’t exactly run-of-the-mill either.
Sam Bennett will have to become even more integral than he already has been. The line of Anton Lundell between Eetu Luostarinen and Brad Marchand will have to produce like it did in the playoffs last spring.
As for the Atlantic Division, if you were already thinking that Tampa Bay and/or Toronto was going to finish ahead of the Panthers in the standings, that belief is strengthened.
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The big battle for Florida might be whether it can finish in the top three in the Atlantic. The door is open for Ottawa or Montreal to make a legitimate push to finish above and beyond a wildcard spot.
Taking everything into account, considering the Panthers’ pedigree, we wouldn’t rule them out of another long run once the playoffs start, no matter their injury status or where they finish in the standings.
Mitch Marner #93 of the Vegas Golden Knights looks onin the first period during a preseason game against the Utah Hockey Club at T-Mobile Arena on September 25, 2025 in Las Vegas, Nevada. Photo by Ian Maule /Getty Images North America
Can Mitch Marner lead the Vegas Golden Knights to a Stanley Cup title?
The biggest off-season address change for any player featured Marner, who departed Toronto after nine seasons with the Leafs.
Marner’s dream since childhood — to help lead the Leafs to a Cup — didn’t come close to happening during his tenure with his hometown team.
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Never one to have much interest in holding himself accountable publicly following post-season failures, Marner’s playoff production didn’t match his regular-season numbers. He averaged 1.13 points per game with the Leafs, but that fell to 0.9 points per game in the playoffs.
Vegas is among the Cup favourites to start, not unlike the Leafs were several times during Marner’s tenure. Despite being part of an excellent nucleus, like he will be with the Golden Knights, Marner couldn’t help make it happen in Toronto.
Players such as Phil Kessel, Nazem Kadri and Tyler Bozak won the Cup after leaving Toronto. Marner has a great chance to become the next ex-Leaf to do so, but it’s certainly not a guarantee that will happen in his first year on the Strip.
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Capitals captain Alex Ovechkin (8) in action during the first period of an NHL pre-season hockey game against the Boston Bruins in Washington on Thursday, Oct. 2, 2025. Photo by Nick Wass /AP
Will this be The Great 8’s last stand?
The greatest goal scorer the NHL has seen — aka Alexander Ovechkin — has one year remaining on his contract.
After turning 40 in September, the Washington Capitals captain has his sights set on building on his record for most goals in NHL history. Ovechkin is sitting on 897 goals, three more than Wayne Gretzky scored during his legendary career.
That Ovechkin will hit 900 goals is obvious. Can he top, say, 930 or 940? And if he goes higher, will that production be enough to convince him to continue his NHL career?
Ovechkin has been saying he has not given much thought to his hockey future beyond this season. To be sure, if you get a chance to watch him play live in 2025-26, don’t pass it up.
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There are no questions, meanwhile, about the future of Los Angeles Kings captain Anze Kopitar. The two-time Cup champion and two-time winner of the Selke Trophy has announced that he will retire at the end of this season, his 20th in the NHL.
From left, Alex Formenton, Carter Hart, Dillon Dube, Cal Foote and Michael McLeod enter the London courthouse on May 20, 2025. Photo by Mike Hensen and Derek Ruttan /The London Free Press
What will become of the Hockey Canada Five?
Goaltender Carter Hart, forwards Michael McLeod, Dillon Dube, Alex Formenton and defenceman Cal Foote will be eligible to sign with an NHL club as of Oct. 15 and can return to action as of Dec. 1.
That was the ruling of the league after the five were found not guilty of sexual assault in July following a two-month trial that was the result of an incident that happened in a London, Ont., hotel room in June 2018.
The most interest has been in Hart, who could, for example, be a key for the Golden Knights and their Cup hopes.
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Any club that signs any of the five will have to be steel itself for public backlash. We’d bet at least one NHL team or two will be willing to withstand the criticism if it thinks it is making its team better — on the ice.
Who makes the cut for the Winter Olympics?
NHL players will participate in the Winter Olympics for the first time since the 2014 Games in Sochi, when Canada beat Sweden 3-0 in the gold-medal game.
Among those on the Olympic bubble and in need of a solid start to earn a chance to play in Italy in February include Canada’s Rob Thomas, Connor Bedard, Macklin Celebrini and Nick Suzuki, and the United States’ Tage Thompson, Jason Robertson, Cole Caufield and Clayton Keller.
Toronto Maple Leafs forward Auston Matthews at practice in Toronto on Friday, Sept. 26, 2025. Photo by Jack Boland /Toronto Sun
How will the Leafs fare without Marner?
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Perhaps more specifically, how will Leafs captain Auston Matthews fare without his right-wing sidekick?
Matthews, for now, is past the undisclosed upper-body injury that lingered through last season and caused him to miss a total of 15 games. In 67 games, he scored 33 goals, his lowest total in any of his nine NHL seasons.
Matthews and Marner became joined at the hip with the Leafs. Had Marner stayed (but don’t consider that possibility, as his interest in joining Vegas had taken root long before the Leafs lost to Florida last May) the line of Matthews between Marner and Matthew Knies would be among the best in hockey.
There’s no doubt that Matthews will be motivated to prove that he can put the puck in the net just as often as he did with Marner on his right. Never mind if Matthews can equal his career-high of 69 goals, let alone 60. Whether it’s Matias Maccelli or Max Domi on the line, it could be a challenge for Matthews to score 50 goals.
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And if not Matthews, does teammate William Nylander score 50 goals for the first time in the NHL?
Other areas we’re keeping an eye on …
— What kind of a difference can future Hall of Famer Jonathan Toews make with his hometown Winnipeg Jets? Toews hasn’t played in an NHL game since April 13, 2023 with the Chicago Blackhawks.
The Jets’ chances at making a Cup run won’t necessarily ride on Toews’ shoulders, but a good comeback season by the 37-year-old would go a long way.
— At the outset, the Calder Trophy appears to be Ivan Demidov’s to lose. After a brief introduction to the NHL with the Montreal Canadiens last season, Demidov, the fifth pick overall by the Canadiens in 2024, is the heavy favourite to win rookie-of-the-year honours.
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Among those we wouldn’t count out of the race are defencemen Zeev Buium of the Minnesota Wild, Zayne Parekh of the Calgary Flames, Matthew Schaefer of the New York Islanders and Alexander Nikishin of the Carolina Hurricanes, as well as forwards Jimmy Snuggerud of the St. Louis Blues and Michael Misa of the San Jose Sharks.
Slice it any way and the conclusion is the same. There’s a heck of a crop of excellent young players set to make an impact in the NHL.
Which teams have the best shot at making a rise in the standings in either conference?
In the East, we’ve mentioned that one of Ottawa or Montreal has a shot at finishing in the top three in the Atlantic. A return to the playoffs by the New York Rangers, now coached by Mike Sullivan, in the Metropolitan Division seems to be a safe bet. The Columbus Blue Jackets should have a shot.
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We’re not convinced that the Detroit Red Wings or the Buffalo Sabres are going to take a big step and earn a path into the postseason.
In the West, the Anaheim Ducks finished 16 points out of a playoff spot last spring. Will the presence of coach Joel Quenneville, back behind an NHL bench for the first time since October 2021, make enough of a difference for the Ducks to make a charge to the playoffs? Probably not, but there’s a foundation in Quenneville that the Ducks have not had in years.
The Vancouver Canucks get a fresh start under new coach Adam Foote. Whether goalie Thatcher Demko can stay healthy will play heavily into a potential return to the playoffs.
X: @koshtorontosun
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