What has to happen this season for the Washington Capitals to win the Stanley Cup?

The play of Alex Ovechkin and Evgeny Kuznetsov is essential to the Capitals' Cup chances. Amber Searls-USA TODAY Sport

Craig Custance: It's all about matchups and health. The team I'd be watching closely if I were a Capitals fan is the Tampa Bay Lightning. I'd be cheering against them as much as I'm cheering for the Capitals. The last thing the Capitals need is the Lightning sneaking into the playoffs in the final playoff spot with Steven Stamkos returning to health. That likely would mean the Capitals would have to go through a gauntlet of the Lightning and Pittsburgh Penguins before even getting to the conference finals. Even so, if the Capitals are healthy, they should be able to beat anyone in the East, but a break in the first round would go a long way toward paving the road for a trip to the Stanley Cup finals.

Joe McDonald: It's very simple, actually: Alex Ovechkin needs to be Alex Ovechkin. He's one of the best players in the world, but he has yet to prove it on the biggest stage. Sidney Crosby has proved to be that player for the Penguins. Jonathan Toews has been that player for the Chicago Blackhawks. Patrick Kane? Yes. The Boston Bruins' Patrice Bergeron? Of course. Justin Williams, who has won three Stanley Cup championships (one with the Carolina Hurricanes and two with the Los Angeles Kings) is Ovechkin's teammate, and Williams' success needs to rub off on Ovechkin because the Capitals have the team to win. If Ovechkin takes his game to the next level, the Capitals will hoist a Cup.

Scott Burnside: I'm assuming the Capitals will win their second straight Presidents' Trophy, which means no other team will enter the playoffs with as much pressure on them. Their historic lack of success in the playoffs will be an ongoing storyline, but this will be the Caps' springtime of glory because they'll embrace that pressure. And they'll get there because Evgeny Kuznetsov will rise to the occasion and, along with the brilliant Nicklas Backstrom, give the Caps the kind of one-two punch down the middle that few teams can match. Kuznetsov struggled last spring when the Capitals were bounced by the Penguins in the second round, and it took him a while to get going this season -- but when he goes, as he is now, Kuznetsov is one of the game's most dynamic offensive forces. If he performs this spring the way I think he's capable of performing, Kuznetsov might in fact be part of the discussion when it comes to determining a playoff MVP.

Pierre LeBrun: Oh man, totally agree with Craig on the Lightning. What a dangerous animal they would be if they sneaked into the playoffs. You know, the team Craig and I (and a few other ESPN analysts) picked to win the Stanley Cup back in October. As for the Caps, though, it's not like they didn't show up a year ago in the playoffs. They laid it all out on the line in the second round against the Penguins in a series worthy of Stanley Cup finals. Ovechkin was terrific in that series. This wasn't the same old narrative of yesteryear. The Caps showed up. But they lost by a hair to the team that would go on to win the Cup. The Caps have all it takes to win it all. But this league is filled with parity; there's so little separating the 16 playoff teams. There are no guarantees. Fewer than ever, in fact.