I think some people are so caught up on accomplishments that are zeroes or ones that tonight is going to have an overweighted bearing on their opinions. If the Oilers fall short, they're going to ding McDavid for falling short of a Cup, even though he practically took over the series for two games to make it a series and had been far from bad before that. A Conn Smythe will help, of course (and my guess is that it's his regardless of the outcome tonight), but they'll still portray him as not being able to get over the hump, regardless of the fact that there's little more you could reasonably ask of him. Even when he wasn't on the scoresheet in game 6, I thought he was still very visible, and the attention that had to be paid to him just freed up teammates. That's another way to have an impact on a game too, after all, but that won't be acknowledged after a loss.
On the other hand, let the Oilers win and the all or nothing crowd may be hyping this up to be the greatest playoff run in history, especially if he finishes it off with a multi-point game. My question is how will one Cup be viewed as compared to multiple Cups for the big four. Will it be chalked up to "he did it in the toughest era to win one" or will it be "he still needs multiple Cups" to be in the conversation with them?
To me, this year doesn't tell us a lot we didn't already know. He's the best player in the world. If he continues at the pace he's on, he's headed for top five all time, and I think this playoff run alone gains him some spots on my centers list. He needs to keep it up to be mentioned in the same breath as our sport's Mount Rushmore, but if he continues to do what he's been doing in the playoffs (this year being a prime example, but something like winning a playoff scoring title without even reaching the final has to be considered too), then he could flirt with Lemieux's level. Let him get a couple of more 150-point seasons while maintaining his level of overall play and the regular season reputation could get there too.