The chance for a rare Stanley Cup threepeat and a return to the biggest stage in sports at the Milan Olympics highlight some of the promise that lies ahead with the start of a new NHL season.

The curtain has been raised on 2025-26 at a fascinating time for the sport, with record-breaking contracts being signed and a cadre of surefire Hall of Famers inching toward the finish line, plus the arrival of a highly touted draft prospect in Gavin McKenna on the horizon.

The game wouldn’t be what it is without the people who work in it.

With that in mind, ahead of the first full night of action Thursday, here are the 25 players, coaches and execs I’ll be watching closely in 2025-26. Who are you watching? This is a subjective list, so share your own most-compelling persons in the comments.

1. Connor McDavid

After finding himself in the middle of the NHL’s biggest offseason storyline, it doesn’t promise to get much quieter for McDavid, even after giving the Edmonton Oilers a surprising hometown discount earlier this week. For starters, the game’s most gifted offensive force is openly talking about pushing his own boundaries and scoring more goals. That bears watching. McDavid also has a chance to record his ninth 100-point campaign, which would move him to third in NHL history behind only Wayne Gretzky (15) and Mario Lemieux (10). Then there are the legacy-cementing pursuits — trying to lead teams to a Stanley Cup and an Olympic gold medal. McDavid will be at the center of it all.

2. Sidney Crosby

Approaching the home stretch on one of the finest careers in NHL history, the focus on No. 87 is completely fixed on whether he keeps powering through the Pittsburgh Penguins rebuild or decides to pursue another Stanley Cup elsewhere. The clock is ticking, even if Crosby is fresh off another point-per-game season — making him 20-for-20 in that regard as an NHL player. Beyond the trade speculation lies the possibility for Crosby to capture a third Olympic gold medal with Team Canada, where he’s expected to again wear the “C.”

3. Kyle Dubas

As he enters his third season at the helm of the Penguins, the heavy lifting is just beginning. Dubas will need a delicate touch to navigate the Crosby situation, plus the possibility of moving pending unrestricted free agent and fellow franchise cornerstone Evgeni Malkin. Even in the event that those two decide to commit another rebuilding campaign to Pittsburgh, the general manager should be a motivated seller with other attractive veteran assets on his roster. The NHL’s trade market has basically been frozen since the summer, but Dubas should be a big player once it eventually thaws.

4. Gavin McKenna

Coming off an eye-popping campaign with the WHL’s Medicine Hat Tigers, the 17-year-old forward is on the cutting edge of hockey’s evolving development system. He made the jump to Penn State — something that wasn’t possible until recent rule changes – and is now being paid like a professional in the NCAA. That speaks to how special his talents are. In fact, if McKenna has the kind of impact many are predicting, he could end up shifting the plans of a couple of NHL teams that may pivot to ensure they put themselves in the best position possible to secure the No. 1 pick in the draft lottery to get him.

5. Mitch Marner

Not only was Marner born and raised in Toronto, but he also became an NHL star in the city before trading in that comfort this summer for a fresh start with the Vegas Golden Knights. Moving three time zones west won’t remove him from the fishbowl entirely. It’s safe to say that fans on both sides of the continent will be closely charting his adjustment to a new environment. Will life with the Golden Knights live up to his hopes? And will playing for a perennial NHL powerhouse help him turn over a new leaf come playoff time?

6. Auston Matthews

Most NHL players would love to “struggle” the way Matthews did last season, when persistent health challenges kept him to a career-low 33 goals. The belief inside the Toronto Maple Leafs organization is that the captain is ready to reach another level with his body rested and healed. Let’s face it: They’ll need the offensive boost to avoid a major falloff following Marner’s departure. This season will also see Matthews make his first Olympic appearance for Team USA and should include a special piece of history: He’s just 20 goals shy of passing Mats Sundin’s franchise record of 420 goals.

Auston Matthews scored 33 goals in 2024-25 after scoring 69 a season earlier. (Claus Andersen / Getty Images)

7. Patrick Kane

Your favorite player’s favorite player, Kane may not bring the razzledazzle he once did to NHL arenas. But the season begins with him on the verge of a major milestone that speaks to both his creativity and longevity — needing just 32 points to pass Mike Modano and become the highest-scoring U.S.-born player in NHL history. Kane is aching to find his way into the conversation for the Olympic team, which has to be considered a long shot. A hot start for a Detroit Red Wings team looking to take the next step is imperative.

8. Jonathan Toews

After playing in just two of the past five NHL seasons, Toews followed his heart back to his hometown to attempt an uncertain comeback. Finally healthy after an Ayurveda detox in India last year, there are still serious questions about how effective the 37-year-old center will be after so much time away. What makes his case especially compelling is that the Winnipeg Jets need him to perform as they look to build on a couple of strong campaigns. Toews has the potential to help that growth along in both tangible and intangible ways.

9. Joel Quenneville

There was no guarantee that the 67-year-old would find his way back to this position after being implicated in the Kyle Beach scandal from his time with the Chicago Blackhawks. Quenneville is making his return to the bench after nearly four years on the sidelines. The four-time Stanley Cup champion returns with an up-and-coming Anaheim Ducks team that not only has one of the NHL’s youngest rosters but also had a fantastic second half last season. They’re facing growing expectations, and Quenneville is being counted on to push them to the next level.

10. Mike Sullivan

Sullivan returns to the New York Rangers as the NHL’s highest-paid head coach, and he’s expected to imprint his Stanley Cup pedigree on a team that lost its way a year ago. It’s a big ask and a major task. The Rangers core is dotted with veterans — even goaltender Igor Shesterkin will turn 30 this season — so the internal growth may have to be driven more by collective play than a strong push from any one or two key individuals. Sullivan will also be behind the American bench in Milan, where the country will attempt to win its first Olympic gold in men’s hockey since 1980.

11. Kirill Kaprizov

The owner of the richest contract in NHL history after signing a $136 million deal with the Minnesota Wild last month, Kaprizov will be shouldering a little extra responsibility in his sixth season. He’s unquestionably The Franchise now. One of the reasons the Wild ultimately extended themselves so far to sign him is how electric Kaprizov was last season — putting himself in the early Hart Trophy conversation before seeing the campaign derailed by a sports hernia. The Wild are counting on him to get back to that level to help push them beyond the first round of the Stanley Cup playoffs for the first time since 2015.

12. Ivan Demidov

Not yet 10 games into his NHL career, Demidov is already a full-blown superstar for the Montreal Canadiens. The 19-year-old winger has game-changing offensive ability and will be the most closely watched player on the league’s youngest roster. He has a strong chance to follow teammate Lane Hutson in winning the Calder Trophy as the NHL’s rookie of the year — a feat players from the same team haven’t accomplished in consecutive seasons since Bobby Orr and Derek Sanderson did it for the Boston Bruins in 1967 and 1968. Expectations are soaring around the Canadiens, and Demidov could tip the scales in a positive direction if he pops.

13. Connor Bedard

Every true assessment of Bedard’s progress must be viewed with the context that he was basically the NHL’s youngest player for two years running and played on a severely overmatched Chicago Blackhawks team during those seasons. While the conditions in Chicago aren’t dramatically different for Year 3 — the Blackhawks may well be a lottery team again — Bedard has another steady summer of training under his belt and more than 150 games of experience to draw on. Plus, there’s a lot riding on him taking a big personal step in the months ahead. Not only will he be trying to draw the attention of Hockey Canada’s decision-makers to secure an Olympic invitation, but he’s also due to score a major raise with the expiry of his entry-level contract at the end of the season.

14. Alex Ovechkin

It may just feel like another year, another huge goal-scoring milestone involving Ovechkin — he’s three snipes shy of becoming the NHL’s first 900-goal man — but this is a campaign for both fans in D.C. and hockey sentimentalists to savor. There is a chance it’s the last tour around the NHL for the Washington Capitals captain. He’s made no official decision on that front, but the 40-year-old is playing on an expiring contract. And he’s dreaming of a scenario where Washington follows last year’s surprising breakthrough by returning to the contender status they’ve carried for most of his time as the face of the Capitals.

Will this be Alex Ovechkin’s last run at the Cup? (Patrick Smith / Getty Images)

15. Anze Kopitar

Out in Los Angeles, there’s no mystery about what comes next for the Kings captain: Kopitar has already declared this season his last, kicking off a rare farewell tour for an NHL star. Expect the classy Slovenian to be feted in a way he so often wasn’t during a sturdy, understated career that’s going to land him in the Hockey Hall of Fame. Kopitar is walking away on his own terms — he’s coming off a 21-goal, 67-point season — and he’d love nothing more than to go out with a long playoff run. The Kings will try to make the most of the time they have left with him.

16. Mikko Rantanen

It had to be unsettling for one of the NHL’s high-end offensive forces to be traded twice last season, going from the Colorado Avalanche to the Carolina Hurricanes to the Dallas Stars in a head-spinning set of transactions. But Rantanen found stability with the $96 million, eight-year contract he got from the Stars — making him a cornerstone of one of the league’s top Stanley Cup contenders. No one would fault Rantanen if he was playing with a little chip on his shoulder, either, particularly with the Avalanche now a division rival. He’ll also be shouldering a big load at the Olympics, where the plucky Finns can never be ruled out of medal contention.

17. Bill Zito

Perplexingly, Zito has yet to win the Jim Gregory General Manager of the Year Award, despite the fact that all of his colleagues would trade their individual accolades for his past couple of seasons. The Florida Panthers GM has locked up basically all of the important pieces that delivered two straight Stanley Cup wins, but there’s no reason to believe he will be putting his feet up while they chase a third title. It’s not in his nature, for starters. Plus, the team is facing the long-term absence of Matthew Tkachuk and the even longer-term absence of captain Aleksander Barkov, who likely won’t be ready to return from knee surgery until the playoffs at the absolute earliest. That puts a big hole in the roster, but it could present some cap-related opportunities for Zito to build on his dynasty.

18. Jon Cooper

On the other side of the frothy Battle of Florida, you have a Tampa Bay Lightning team with designs on reclaiming former glory. And they’re doing it with Cooper behind the bench for a 13th straight season. That’s an impossibly long time in a “what have you done for me lately?” league and speaks to Cooper’s unique ability to continually find new ways to bring the best out of his athletes and keep the program from growing stale. There’s no one else quite like him in hockey. He’s also going to be behind Team Canada’s bench at the Milan Olympics, which means for two weeks in February, he’s going to have his decisions more closely scrutinized than the Prime Minister.

19. Rasmus Andersson

Andersson is eyeing his own Olympic invitation from Sweden, but that’s not what is going to have him front and center this season. As a pending unrestricted free agent with an uncertain future with the Calgary Flames, he’ll be a mainstay on the trade boards and in the league’s hot stove chatter. Quality right-shot defenseman don’t typically change addresses before their 30th birthday in a league where every team forever has a need for that type of player. While the door isn’t fully closed to an extension with the Flames, both sides understand that Andersson may ultimately be moved before the March 6 deadline.

20. Artemi Panarin

The NHL’s free agent class of 2026 has been gutted by the recent wave of big-money contract extensions, leaving Panarin as potentially the biggest name available. His age may be a slight deterrent by next summer — he turns 34 this month — but it should be noted that he’s led the Rangers in scoring in all six seasons since he landed on Broadway as a hotly pursued free agent in 2019. Of course, New York could still move to extend Panarin now that other big-name targets are off the board. One way or another, he’s a good bet to land another monster deal in a surging salary cap environment.

21. Nikolaj Ehlers

When Ehlers hit the open market in July, he ended up having to decide between two of the Metropolitan Division’s top teams, with both Washington and Carolina showing strong interest. He opted for the Hurricanes, a team that flies a little below the radar from a national perspective but always seems to punch above its weight class. They’re trying to push their group forward by adding more high-octane offensive drivers who can fit into a system that has brought a ton of success. Ehlers should find minutes and opportunities in Carolina that weren’t always available to him during his days in Winnipeg.

Nikolaj Ehlers played all 10 of his NHL seasons with the Jets before joining the Hurricanes this offseason. (James Guillory / Imagn Images)

22. Elias Pettersson

Last season was loud for Pettersson. Really, really loud. Even though an unharmonious work environment ultimately saw the Vancouver Canucks trade away J.T. Miller while hanging onto the Swede, there’s no getting around the fact that Pettersson finished tied for 155th in NHL scoring while earning the league’s fifth-highest salary. He’s got a lot to prove, and the Canucks desperately need him to return to being a difference-maker if they’re going to be a playoff team.

23. Quinn Hughes

The Canucks captain is in a unique position with so much focus and conversation on his future in Vancouver, even though he’s not eligible to sign an extension before July 1, 2026. His brothers, Luke and Jack, have both been locked up long-term by the New Jersey Devils. Quinn took the losing particularly hard last season and saw his frustrations compounded by a series of injuries that forced him out of the 4 Nations Face-Off. A fresh campaign represents a fresh start for Hughes. It will give him an opportunity to represent Team USA at the Olympics and promises to come with a big decision on his NHL playing future next summer.

24. Cale Makar

If Quinn Hughes doesn’t win the Norris Trophy in 2025-26, it’s a good bet that Makar will. They are at the top of the food chain among NHL defensemen. They’re also set to reestablish the going rate for the position concurrently, with Makar also eligible to sign an extension with the Colorado Avalanche next July. He’s approaching the territory where he’ll basically be able to name his price when the time comes. In the meantime, he’s a key cog for both a team trying to win the Stanley Cup and a Team Canada trying to maintain its grip on Olympic gold.

25. Gary Bettman

With a CBA extension hammered out more than a year ahead of time and national media rights deals secured on both sides of the border, the NHL commissioner can devote his energy to broader aims for the league. That could include movement on expansion in the coming months — although officially Bettman says that’s not a front-burner issue for the NHL head office — or perhaps even a more concrete succession plan among the senior leadership in his office. At age 73, Bettman will mark his 33rd year in office come February.