When Montreal becomes more of contender (4more years, maybe 5), players like Stamkos (33), Hedman (32) and Kucherov (30) will be on the downswing of their careers, if not even retired by then. Who will Point, 31 or 32,by thence playing with?
It's unrealistic to expect that TB will draft another Stamkos, Hedman, or Kucherov, by then. Those players are few and far between. When Montreal starts truly competing, TB will be in a position like Boston finds itself today, with the cornerstones of their current offense either goner nearly gone and not producing like they did in their prime.
Toronto has a greater chance of remaining relevant with only Tavares gone by then, even though I don't believe that the character of their core will lead to a Stanley Cup.
Same with EDM that should still be milking McDavid and Draisaitl foray they are worth. Only Nugent-Hopkins should be on his way out by the time Montreal is truly competing, but,again, because of the top-heavy Cap structure in Edmonton, that team will likely lack the depth to win a Cup.
Colorado, IMO, will remain one of the biggest threats to win the Cup by the time Montreal aspires toddling as much, with only Johansen and Cogliano on their way out, or already gone at that point.
Younger teams like, BUF, if they continue building properly their talent pool and continue applying the same cap structure, will become the next powerhouses, but I think Montreal will be able to match up favourably -- if the current prospect pool tops out closet their ceilings in at least 50% of the cases.
That means Hutson or Reinbacher becoming an impact, top-pairing D, Mailloux or Engstrom becoming a solid 2nd pairing D, Roy or Newhook reaching their ceiling and other prospect not currently in the system topping out as middle-six forwards, or quality third and fourth liners; Beck, Heineman, RHP, etc.
Caufield - Suzuki - XXX
Slafkovsky - Dach - Roy/Newhook
RHP/Heineman - Beck - Newhook/Roy
Farrell - Kidney - Heineman
Missing ingredients, like a winger for the Suzuki line will either come from players like Roy exceeding expectations, a trade that weaponizes Cap space or the UFA market.
IMO, we will only know the true nature of the forces on hand in at least two, if not three, years.