If Ovechkin cannot guide his team back from the 3-1 series deficit it faces, with a possible season-ending game set for Saturday night, 7:15 ET, at Verizon Center in Washington, will it somehow diminish all that Ovechkin has accomplished?
Difficult questions, but these are difficult times for the NHL's best regular-season team.
"I think it's too easy for people to attack his legacy if something like this happens," said former Capital and longtime analyst Alan May on Friday after the Capitals went through a spirited workout at their Arlington practice facility.
"But when you look at how well he's played in these playoffs, the heart and the soul that he's put into the game, what he continued to do during the regular season, I don't think it can affect him."
In some ways, the story of this series is the story of Ovechkin versus Crosby, head to head.
Close but no cigar for the great Russian winger.
Going back to their days in the world juniors, when Crosby's Canadian team overwhelmed Ovechkin and Evgeni Malkin and a powerful Russian squad in North Dakota in 2005 in the gold-medal game, Crosby has dominated these confrontations.
There was, of course, the epic 2009 second-round series won by the Pittsburgh Penguins in a Game 7 blowout at Verizon Center.
The next season, Crosby's Canadian team crushed Russia in the quarterfinals of the Vancouver Olympics en route to a gold medal thanks to a Crosby overtime goal against the U.S.
Ovechkin's host Russian team didn't play Canada in Sochi but was bounced in the quarterfinals as Crosby earned his second straight gold medal.
And now this, the Capitals having dropped three straight one-goal games to face an early playoff elimination once again.
The two great players have spent a lot of time on the ice together in this series. They have combined for one goal (that by Ovechkin) and three assists (two from Ovechkin), and, although both have played well, this has been a series marked by key contributions from Penguins up and down the lineup.
Ovechkin has been a physical force.
One scout said that, in spite of a quiet Game 4, he's been impressed with Ovechkin's game.
"I have been impressed with his overall play," the scout said. "He has been playing a hard game. He has played a powerful, physical and disciplined game. Caps need some better play from some of their other stars."
Coach Barry Trotz tried out new line combinations in Friday's practice, moving struggling Evgeny Kuznetsov to a line with Ovechkin and Game 1 hat trick heroT.J. Oshie.
And he said he would consider trying to get more separation between Ovechkin's line and Crosby's line.
"They're getting chances," Trotz said of his top line. "They're not getting a lot of production. There hasn't been a lot of production."
As for Ovechkin, it must be difficult for him and his teammates to consider that their season hangs in the balance at this stage of the playoffs, given how dominant they were throughout the regular season.
"Of course it's a position you don't want to be, obviously, but, at the same time, you have to fight through it," Ovechkin said Friday.
"I think it's a huge test for us. We're going to take this test, and we'll see what's going to happen. We're going to fight through it, and we're going to do our best."
The Washington captain, who has never played beyond the second round of the playoffs, insisted the Capitals aren't frustrated.
"It's not frustrating," Ovechkin said. "If you're going to be frustrated, you're probably not going to have a chance to bounce back and win the game. You just have to win game by game. Last year, we were up 3-1 against the Rangers and it's every situation matters. A little play can turn around a series. We want to win tomorrow, and we have to win tomorrow and go back to Pittsburgh."
Former NHL goaltender and current broadcast analyst Brent Johnson is in a unique position, having played with both Crosby and Ovechkin. He believes Crosby, who has created scoring chances throughout the series, is due for a bust-out game in terms of offensive production.
"If he has a breakout game in Game 5, then it's all over but the crying for Washington, I think," Johnson said Friday.
But what would that mean for Ovechkin's legacy as a leader, especially given that Crosby is on the other side of the ledger?
"I'm probably on the fence about that," Johnson said. "You look at Ovi and you can see the care in his eyes. You can just sense it. He understands that this is the time. He's got one of the deepest teams and one of the best teams he's played on ever, and now you're down 3-1 and you're like, how did this just happen?"
Part of the dynamic in this series, where all four games have been decided by one goal, two in overtime, is the lack of good fortune for the Caps.
"The Capitals haven't had good luck at all. They haven't had good bounces," Johnson said. "I can't look at it and say Ovi would be to blame if this series goes awry on the Capitals."
It is a testament to the greatness of Ovechkin and to the greatness of his rival with the Penguins, Crosby, that we can debate the notion of legacy in these rare head-to-head confrontations.
And even though the scorecard historically has been dominated by Crosby, what makes Saturday so compelling is that Ovechkin has it within his grasp to draft a new script, to defy the past.
Just as he has had those opportunities in the past but could not change the narrative.