This time two years ago there were real questions on Sidney Crosby‘s odds to finish his career in Pittsburgh. To the credit of general manager Kyle Dubas and the rest of the organization, that no longer applies.

Entering a contract year again this season, what’s different this time around is there’s much less concern. According to Josh Yohe of The Athletic, it could be a “similar timeline” as when the future Hall-of-Famer re-upped on a two-year deal on September 16, 2024. Back then it was opportune timing, right before taking the ice for training camp, which would have been a distraction with each passing day of the 2024-25 season. This time around, even sparing us from wild trade hypotheticals being thrown every which way, Crosby watch is on for another agreement in the coming weeks.

Back in May there was a clear sentiment that although the recently-turned 39-year-old is taking it year-by-year in the twilight of his career, he still wants to play for as long as possible. Some sort of retirement tour in 2026-27, even if in typical quiet Crosby fashion, doesn’t seem to be any real possibility. It’s pretty remarkable to consider that he and Alexander Ovechkin, who had his own retirement speculation, will run it back in a season where players like Gavin McKenna will debut, born in late 2007 which was well into the era in which #87 and #8 were established superstars in the league.

Having the cap room for Crosby won’t be any concern. As Yohe wrote, the soon-to-be 20-year captain of the Pens will continue his ways of not being pushy in salary negotiations. Currently under contract at a symbolic cap hit of $8.7MM, it seems to be right on the dot. AFP Analytics projects that the center would be worth another year at the same value. The Penguins currently have over $10MM in cap space, with notables Erik Karlsson and Evgeni Malkin both coming off the books next summer, among others. If anything, the financial comfort is an indication of an overly passive off-season, a point which has already been raised. Pittsburgh lost their leading goal scorer Anthony Mantha, and while they were mentioned as a fit on blockbuster trade rumors for Jason Robertson, it’s his more modest-producing brother Nicholas they picked up instead. That’s not to say Dubas couldn’t still pull something off either via trade or free agency, but either way Pittsburgh will comfortably fit in a Crosby extension with ample space to cautiously supplement their team without mortgaging the future.

Going back to 2024, the future was pretty bleak in Pittsburgh, not sniffing the playoffs as efforts to set up one last dance were futile. Impressively, Dubas has assembled a well-regarded prospect pool, Crosby, Malkin, and Kris Letang are all still wearing the black and yellow, and they’re a respectable playoff team. Falling in the first round of last spring’s postseason to their in-state rivals stung, yet even getting to that point seemed impossible not long ago.

Having evolved his game into a more cerebral pivot, able to slow the game down in the most perfect way, Crosby’s impact in the lineup continues to be massive. To imagine him around age 40 fading into more of a 3C role would still be an incredible player based on his skill-set. Instead the 2005 first-overall pick will be a standout scorer to the end, posting 74 in 68 games last year, the 21st consecutive time he surpassed the point-per-game mark. It was all despite dealing with a knee injury sustained while leading Team Canada at the Olympics. The total was good for best on the team by an eight-point margin even with the missed time. Only he and Letang remain as active 2005 draftees, depending on Ryan Reaves‘ contract status this fall, and there’s more records to come. As pointed out by Pro Hockey Rumors’ Ryan Long yesterday, Crosby needs just three helpers to pass Joe Thornton‘s 1,109, seventh all-time. It’s realistic he could move up to fifth all-time by season’s end.

With Ovechkin back in Washington, Patrick Kane returning to Chicago, and finally, Sid the Kid still doing his thing in the Steel City, 2026-27 has shaped up to be a campaign full of nostalgia. Eyes will be on the Penguins to take care of Crosby’s next extension sometime in the next 30 days, allowing the franchise to turn attention to other matters. Once that’s done, it’ll be fascinating to see what he has to offer toward what could be a storybook ending.

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