Some possible projections:
- Let's assume he hits 85 points this season and next - that puts him at 1672 points by end of next season and contract. If he does retire after his contract, #9 all-time behind seems inevetable, since there's a really big gap between #8 and 9 right now.
Patrick Roy and Wayne Gretzky retired when they were still near top of league at ages ~37-38. It's not unprecedented - and always hard to predict when a player will retire.
I do think if Crosby continues to play - it won't be a 1 year contract, but minimum of a 2 year contract.
- So if he does play 2 years after that - let's be conservative and assume 75 points per year. That puts him at 1822 points at age 39, or #5 (also a big gap between #4 and #5 right now, so finishing 5th seems quite likely).
Meaning - he'd have to play at minimum 1 more year beyond that to have a chance at Jagr and #2, so age 40. Obviously, he probably won't score 99 points at age 40 to pass Jagr, but it's possible he scores a bit more in prior seasons and that by age 40 he can surpass 1921 points, or at worst, by age 41.
So to sum up, some possible scenarios:
- If he retires after his contract - he will almost for sure finish #9 right behind Lemieux.
- If he extends for 2 years and retires at age 39 - very good chance he finishes #5 all-time, ahead of Francis but below Howe
- If he plays for 1 more year on top of that (age 40), he likely makes a run at Howe (1850) and Messier (1887) - and possibly Jagr (1921). It's probably more likely Crosby would need +1 year to surpass Jagr though.
- If Crosby does play till age 41 - good chance he passes Jagr and starts to push for 2000 points, which he either hits at age 41 or 42.
This is barring any major injury (minor injuries are fine), and barring him falling off a cliff in play (which in my opinion 100% won't happen - he'd probably retire if it did).