You’re arguing about what will ultimately come to semantics over the definition of Superstar. So the question comes down to whether failing to win a cup affects a players legacy. I do see where you’re both coming from and are both right to varying degrees.
So we are saying that McDavid is as good as anyone in today’s game talent wise. However, does he have the x-factor to take a team over the top?
There’s a strong argument for saying that in the salary cap era and with the level of parity that exists that to belong in the bracket of being a truly generational player you need a cup. You need to make the players around you better, and that should take your team over the top at least once. I agree with the general premise of this but you have to consider the car crash that the Oilers organisation is. McDavid isn’t benefiting from parity and is playing alongside a truly terrible roster. For me Gretzky is the GOAT and I’m not convinced that adding peak Gretzky, with the benefits of modern times, would takes these Oiler’s over the top. They are that bad. So in McDavids case I think we will be able to judge him an exceptional player, even without a cup, if his peak years are wasted away as an Oiler.
Teams will always win cups without generational players, especially in the cap era.
Dionne has to be adjudged on a different criteria as he played in an era without parity and his best days were on a Kings team that was never winning a cup. Swap in any other Superstar and that team doesn’t win. You have to judge based on the teams a player is on, and any criteria for determining a Great/Superstar/Special player can only ever be a guideline, there will always be exceptions.