If I was Crosby I'd do it.

But if this was on the table I feel like the Penguins would offer ownership of their team too and Crosby would much rather own a bit of the Penguins than the Canadiens.

FSG Would match that hands down.

Lebron James already has equity in FSG and it would be easy for them to pivot and give Crosby equity as well. That gives them two of the best ever in their respective sports.

Nice thought though.

I feel like the NHL would shut down a team providing partial ownership to a player as obvious cap circumvention.

The next 3 years of Crosby are worth more to the Habs than they would be the Pens. We have the young core needed to win after adding him, Letang, and Guentzel. The pens don’t. Cup # 25 would actually be achievable. And he would galvanize an entire province for years.

Pens have nowhere near as much value as the Habs. Nor would his presence cause it to have more value. He’s already there.
Crosby being here would create so much interest, the value of the team might close to double.

The league would be first in line to want to see this happen. It would create so much buzz in a hockey mad market, it would only be good for the league. And this would be a CBA issue for compensation. The league can’t do anything. Just like LTIR changes that are being speculated.

The value of 95% (maybe even 100% honestly) of professional sports teams in North America are on a straight upward trajectory.

He has no connection to MTL other than growing up watching them and being a fan. He built his career and his name in Pittsburgh and idolized Mario who was the owner of the Penguins at the time (still own's a small portion of the team) and continues to follow in his footsteps in how he's carried himself around the sport of Hockey.

The Habs are also owned by a family, where as the Penguins are now owned by an entity. Family's will be less inclined to GIVE an outside individual ownership into something they own simply for publicity. (even if that person is Sidney Crosby) They are going to want that person to pay for ownership, not be given it for free. Where as an Entity like FSG would have less issue doing so. FSG could also offer much more to Crosby in the sports world in general as they continue building out their sports portfolio. He also loves Baseball, FSG can connect him to that world.

It's a fun dream you have though, it won't happen.

Probably not. But maybe 😁

Don't think it's possible anyway.
Cap restricts compensation. You can't offer financial incentives in place of salary. It's circumvention.

When there’s a will, there’s a way.