He will probably end up winning at least one.
The real question is whether or not he will be playing at the best player in the world level we’ve seen for him in the playoffs for the last couple of years while doing so or if he’s going to do it in more of a complementary role in the twilight years of his career.
Good question. It is really strange. On one hand, you can obviously suggest, I don't care how good one player is, he's not able to win a championship without having a good supporting cast, it just doesn't happen in hockey. On the other hand, if you look at the greatest players of all time (subjective ranking of course).....they've all won a cup. Now, you can make the argument it was easier to do so in the past, well, not just an argument, it was factually easier to do so....less teams, it's just math, but also subjectively easier because you might have great players wanting to go play with great players and it was easier to do so in prior eras.
In the modern era though, you've had some great teams being able to compete and win a lot (CHI, PIT, TB). I think you need to get lucky with drafting.....generational players don't come along that often....by definition, and if you get one, those types of guys do make players around them better....some better than others. McDavid hasn't done that any less than Crosby, for example. The challenge then becomes being able to compete for the cup during a period of time. A lot of times, it's hard to keep players if they get too good, too expensive to keep everyone together, so their tends to be a smaller window of time.
You can say all those types of things and then there is also the luck factor and the health factor.