Before I even consider this possibility, let's get something straight, Sidney Crosby will always be a Pittsburgh Penguin and in a likelihood, it will be the only uniform he will ever wear throughout his NHL career.
Crosby in his nearly twenty years in Pittsburgh has developed into in my opinion, at the very least one of the top 10 players in NHL history. Crosby has consistently had the Penguins in playing into the post-season which included a 16-year-long consecutive playoff apperance's streak which went from 2007-2022. Throughout those runs, Crosby and the Penguins appeared in 5 Eastern Conference Finals (2008, 2009, 2013, 2016, 2017), and 4 Stanley Cup Finals (2008, 2009, 2016, 2017) while also bringing 3 Stanley Cup Championships (2009, 2016, 2017) to Pittsburgh. Despite all the championships and success the Penguins have had in the SC87 era, reality has now set in Pittsburgh, which means, sadly for Crosby and the Penguins, all good things must come to a close.
Heading into year 20, Crosby is still playing at an elite level and still a consensus top-10 player in the league at nearly 37 years old. Even with his high level of play, the Penguins have missed the post-season the last two seasons. With one year remaining on his contract, Crosby probably does re-sign with the one franchise he has ever known, but there is always the possibility that a player as competitive as Crosby, could be open for a change of scenery that either allows him to chase one final Stanley Cup to match Wayne Gretzky's four or even allows him to live out dreams he always had as a kid in Cole Harbour, Nova Scotia.
As slim as the chances are, here are five teams I could see Crosby starting the 2025-26 season if he and the Penguins decide it is in the best interest of both parties to part ways after a historic 20 years together.
Crosby Decides To Suit Up For His Childhood Favourite Team in Montreal
A pipe dream? Of course, but let me at least explain my logic. I will fully acknowledge that of all the teams on this list, this would probably be the most unlikely as if Crosby leaves Pittsburgh, it would most likely be for a team that is closer to a championship.
However, Crosby has stated on many occasions that he grew up as a Montreal Canadiens fan as they were the team that drafted his father Troy in the 1984 NHL draft at 240th overall. Unfortunately for Troy, he never got to wear the red, white, and blue at the pro level. Therefore, would it not be a sort of a storybook ending for the Crosby family if Sid decides to end his hall-of-fame career playing for the team that made him fall in love with the game while also getting be a part of a young team on the rise with players such as; Nick Suzuki, Cole Caufield, Juraj Slafkovsky to some of the young talent in Montreal.
I'm just saying, it's not impossible.
Crosby Takes His Talents to South Beach
The Florida Panthers just won the Stanley Cup and should remain one of the Stanley Cup favourites across the NHL over the next couple of seasons despite having some key free agents this summer.
If the Panthers do decide to let a player such as Sam Reinhart walk this summer, his 57-goal production would be tough to replace right away, but if the Panthers can at least fill the void for one season and remain competitive in the East next year, I would not be shocked at all if Crosby decides to pull a Tom Brady and start prepping for his post-playing career, while also remaining one of the top teams in the NHL. The Panthers currently have a projected 41 million dollars in cap space to work with in the 2025 off-season, but will need to extend players such as Aaron Ekblad, Carter Verhaeghe, as well as Sam Bennett, should they decide to keep him.
Hypothetically, and to stay on the safe side, say the Panthers have at least 12-15 million left over (they could even have more) to spend a year from now, would Crosby be open to a 2-3 year deal that gives him about 9-10 million dollars a year to live in Florida with state income tax while remaining on one of the top teams in the league? I'm sure he'd at least consider it.
Crosby Links Up With Jim Rutherford & Patrik Allvin
After being one of the biggest dumpster fires in the NHL years, the Vancouver Canucks are so close to a Stanley Cup. In 2023-24, the Canucks shocked the league by finishing 50-23-9 and enjoyed the team's best season since the franchise's last appearance in the Stanley Cup in 2011 where they took the eventual Western Conference Champion Edmonton Oilers to game seven of the second round.
If the Canucks can have a similar season next year where they reach at the least second round, Vancouver management Patrik Allvin and Jim Rutherford showed this past season they are not afraid to make a splash if they deem it necessary. If the Canucks come up just shy of the Final again, could the two men who came from Pittsburgh and won two Stanley Cups with Crosby try to lure the legend to Vancouver to try to be the missing piece of one of the best young cores in the NHL?
Vegas Does Vegas Things
If we've learnt anything about the Vegas Golden Knights since they entered the NHL in 2017, if there is a superstar player even slightly available, they will make a push to go all in on said player.
When healthy, the Golden Knights potentially have the best roster in the NHL, but that does not mean they aren't afraid to get better. If the Golden Knights have another early playoff exit next season where their offence goes cold yet again, is it not the most Vegas thing to somehow find a way to clear the cap space they would need to at least be competitive in the Crosby sweepstakes should somehow be available on July 1st, 2025. As well as much like Florida, Nevada being a tax-free state would have to be appealing to Crosby, especially if the Golden Knights are still considered one of the league's top contenders a year from now.
The Cole Harbour Connection
Nathan MacKinnon has not been shy throughout his career to state how much he has looked up to Sidney Crosby and how special it would be to take the ice with him as a potential teammate.
Now, with captain Gabriel Landeskog's career up in the air due to injury, the Avalanche may need to make finding help on offence for MacKinnon a top priority for their league MVP. If Crosby does make it to the open market next July, even despite their limited cap space, the Avalanche would have to be considered one of the heavy favourites to lure Crosby away from Pittsburgh as they could offer him perhaps the best chance at winning another championship while being paired up with one of his closest friends in the league in MacKinnon, as well as the best defenseman in the league in the NHL in Cale Makar holding down the blue line.
If Crosby leaves Pittsburgh, the Avs would have to be taken very seriously as the place Crosby could end his storied NHL career.
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