Will Sidney Crosby and Nathan MacKinnon ever play together?

Elliotte Friedman had an interesting note in his latest 31 Thoughts:

Every time I see a Sidney Crosby/Nathan MacKinnon commercial, I wonder if they’re going to find a way to play together some day.

Crosby and MacKinnon have long have a bond and kinship, despite an eight year age difference. They’re from the same general area in Halifax, Nova Scotia, both understand the pressure of being No. 1 overall picks in the draft, train together and hang out a ton in the off-season, whether making commercials or golfing with the Spittin Chiclets crew of other Penguin alumni in Ryan Whitney and Paul Bissonnette (NSFW language on that link if the mentions of Whitney and Bissonnette didn’t give that away).

In fact, even last month MacKinnon shared a picture of the two buddies gearing up for the start of the season.

Would they ever play on the same team? It’s just a throwaway aside from Friedman, but not out of line with athletes these days. This practice is pretty common in the NBA, where top stars band together off the court and figure out ways via trades or free agency to join forces and create a super team.

Could it happen in the NHL with Crosby and MacKinnon?

The answer is surely not anytime soon. MacKinnon is under contract to the Colorado Avalanche for three more seasons (at a sweetheart $6.3 million per year). Crosby is under wraps with the Penguins for five more years. Neither team would even start to entertain the idea of trading their superstar away, so expecting this any time soon is just totally out of the picture unless you have a Playstation or something.

...But MacKinnon is scheduled to be a free agent in summer 2023. By then, as of now anyways, the Penguins don’t have Evgeni Malkin or Kris Letang under contract, and only have $32 million on the books for that future season.

For the principals involved, it’s way too early to think seriously about this. Crosby will be 36 in that season, MacKinnon 28. Over the next three years, MacKinnon may well lead the Avs to a Stanley Cup and really cement his place and legacy in that organization and not be looking to make a change. A lot can happen in three years.

MacKinnon eventually re-signing would be the natural and most likely course of action, because star players in this era just do not change teams in their primes, by and large. Of the top-20 active NHL leading scorers, 12 of them have played for only one NHL team their whole career. Several more like Jason Spezza and Patrick Marleau have only changed teams at the tail-end of super long runs with their initial organizations as they chase elusive Stanley Cups.

The exception to the rule is when a John Tavares or Zach Parise does sign with a new organization in free agency while at the height of their careers. However that is very much path less taken, with players like Crosby, Evgeni Malkin, Alex Ovechkin, Patrick Kane, Steven Stamkos, Jonathan Toews, Nicklas Backstrom, Patrice Bergeron et al. opting to remain with one team for their entire careers. (Or, at least the most meaningful parts of said careers).

But, this is a fun dream to dream from the outside, at least. MacKinnon signed a long-term deal in 2016 juuuust before the RFA market exploded and within just a few years of his contract his chief player rival in Connor McDavid makes almost double the Nate Dogg with a $12.5 million cap hit. Ditto Auston Matthews and Mitch Marner who pull in about $11 mill a year.

The Avs already had to ante up $9.25m for a very-good-but-not-as-good-as-Mac player in Mikko Rantanen. Colorado captain Gabriel Landeskog is up for a new deal soon too which will take up UFA years and surely blow past what MacKinnon makes too.

Does any of that bug MacKinnon? Maybe not, but deep down the timing probably has to be a bit aggravating for his sense of timing. What better way to strike back than signing a rich free agent deal in Pittsburgh? Crosby played left wing in his early days, maybe he slides back over in the end of his career to form a super-line with MacKinnon?

Three years out is a lifetime in hockey terms, it may not be feasible for any number of reasons. However, any seeds planted in the Crosby-MacKinnon friendship could only prove to be a good thing for the Penguins one day down the line. The 2022 Olympics might also prove to be a key moment. Both Crosby and MacKinnon will likely be teammates for the first time in real games for Team Canada, a stacked team expected to win gold. If that happens and with Nate Dogg about 16 months out from UFA at that point, would his interest be piqued at being permanent teammates with his buddy?

Maybe. Probably not. Sid and Nate may not be anything more than international teammates, training buddies and marketing co-stars, but in sports as in life, never say never when it comes to the future. Way, way, way in the future.