Pittsburgh 2009 was not very good, neither is Edmonton 2024 since we're talking Stanley Cup teams, and if the health situation of the two teams in 2024 had mirrored what Crosby found in 2009 Edmonton wins the Stanley Cup in five games. If McDavid had been more of a leader Draisaitl/Kane would have been healthy and Barkov/Forsling/random Panthers would have gotten hurt. Is it a blight on McDavid's record as a leader? I say yes! I see zero Messiers in his future!
Ah, the tried and true "what if" game.
What if Bouchard was clearly hobbled after a knee-on-knee hit from Miller in Round 2? Do the Oilers even get past the Canucks?
What if the Panthers were not a disappointing SC finalist the previous year but the clear best Cup winner since the 2005 lockout and as close to a dynastic franchise in the modern era as you can get? Do the Oilers even sniff a Game 5 let alone a Game 7?
But closer to reality, what if McDavid produced earlier in the SCF and not until it was effectively too late? Who cares that he "cemented" his legacy with what are now meaningless points? To quote Ricky Bobby, "If You Ain't First, You're Last"
The original comment was about "leadership" and "winning". It was rightly pointed out that Crosby in 2009 notably scored the first goal in 6 games, two of which opened the series. He took care of business early. And also took care of business early in his career.
McDavid may be destined to be rated higher than Crosby when it is all said and done given he has been more fortunate with injuries after his first nine seasons and that his game is completely suited to the higher scoring environment he plays in which allows for gaudy numbers to impress fans. He is like Hull and Jagr, IMO, where his playoff resume, despite being lacking vs. their all-time peers, reflects his regular season level of dominance.
But this should not change the fact that Crosby is a winner in every sense of the word and won while dragging some mediocre teams and, more notably, mediocre linemates.