A tight salary cap prevents the best teams from retaining all of their top talent, while a wave of new stars has propelled the league’s worst teams back toward the top at an accelerated pace. Keeping a championship window propped open rests on managing team pay structure to afford superstars without sacrificing depth.

When the Penguins won back-to-back titles in 2016 and 2017, they became the first team to do so in 19 years. As the Capitals now hope to parlay their first Stanley Cup into another, they have to weigh decisions to win now with what’s best for the organization’s future and sustaining success long term. Perhaps they can learn from some of the missteps of other past champions.

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“It seems that teams can make a jump faster than they used to be able to by a couple key guys and making the right moves,” Capitals General Manager Brian MacLellan said. “It goes the other way, too, where teams do one or two things wrong and they’re gone. They’re at the bottom of the league. The shifts are more dramatic than I think they’ve ever been.”

The Chicago Blackhawks won three Stanley Cups in six seasons from 2010 to 2015. But as the team repeatedly ran into salary-cap constraints, it traded away talent to get out of some bad contracts while the players left on the roster got older and slower in a league that’s skewed younger and faster. The Blackhawks fired Joel Quenneville, the second-winningest head coach in NHL history, in early November and they have the second-fewest points in the league through Monday’s results. The only team worse? The Los Angeles Kings, who won Stanley Cups in 2012 and 2014 but then also got caught with an aging and expensive roster.

“You don’t really see the so-called dynasty too much more in the NHL,” Chicago forward Patrick Kane said. “That’s probably more geared toward other sports. … It’s a little bit different than when I first came into the league. I don’t want to say you had some easy matchups, but going into some games, you knew that you were better than the other team. Now, teams are so even.”

Maybe this down cycle for both the Blackhawks and the Kings is just the cost of winning multiple championships, in which case both might argue it was worth it. A common thread was awarding big-money contracts to keep Cup-winning core lineups together, and while some of those deals may have seemed reasonable at the time, they didn’t age well. Chicago defenseman Brent Seabrook, whose play has declined to the point where he was a healthy scratch in one game last season, is under contract through 2023-24 with a $6.875 million salary cap hit. Los Angeles has five players over 30 making at least $5.25 million for two more seasons after this one.

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MacLellan avoided getting wrapped up in Stanley Cup sentimentality this summer when he let longtime center Jay Beagle sign with the Vancouver Canucks in free agency. Committing to Beagle, who’s 33, for multiple seasons might have created a salary squeeze in Washington next summer for upcoming restricted free agents Jakub Vrana and Andre Burakovsky. MacLellan also chose to trade veteran defenseman Brooks Orpik at the NHL draft in a move that created cap space to re-sign John Carlson. While Orpik ultimately ended up back in Washington anyway, dealing away a locker-room favorite was a bold move just two weeks after the team won a championship.

But emotion will play into decision-making at some point. MacLellan sees the current Stanley Cup window as this season and next, when goaltender Braden Holtby, center Nicklas Backstrom and captain Alex Ovechkin are all still under contract. So the objective in the meantime is to surround those three with a good supporting cast. Holtby and Backstrom are scheduled to become unrestricted free agents at the end of the 2019-20 campaign, and Ovechkin’s contract is up after the following season. Those two offseasons appear to be when the Capitals will set aside their dispassionate objectivity regarding the roster.

“We’re going to be sentimental with Ovi and Nicky for sure,” MacLellan said. “Because they’ve been here forever and they’ve done what they’ve done. I think you have to be. They’ve defined this franchise. You can’t be that cold.”

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The last time the Capitals’ window appeared to be closing was after the 2016-17 season, when Washington had several contracts expiring at the same time the league faced its first expansion draft in 17 years.

“I think you’ve got to keep the right guys,” MacLellan said, and for him that meant retaining right wing T.J. Oshie. Though Oshie was 30 at the time, MacLellan signed him to an eight-year, $46 million deal, gambling on the salary cap continuing to rise and Oshie remaining productive well into his 30s. But what reassured him it was the right decision was that Oshie’s presence in the locker room would stay the same and be well worth it, even if his scoring eventually drops off. That contract has arguably already been validated with a Stanley Cup.

Washington has seven players signed beyond 2021, so as those players get older, “you’ve always got to have young guys coming in,” MacLellan said. “I mean, we have Vrana, Burakovsky [and center Evgeny Kuznetsov] and then we’re going to need another level after that if we want to keep it going.” With that in mind, the Capitals have been more conservative in trading away draft picks or prospects over the past year, mindful of restocking the cupboard.

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“You have a window where you can create depth and max out your salaries, and then you’ve kind of got to regroup after that,” MacLellan said.

But regrouping doesn’t have to come at the cost of winning. Pittsburgh has built around superstar centers Sidney Crosby and Evgeni Malkin, and the pieces flanking them have been mostly been young, cheap and expendable if the team needs a change. Kris Letang, Patric Hornqvist and Phil Kessel have become mainstays, but the Penguins have stayed contenders because they’ve managed to plug in other players around their core, like speedy wingers Bryan Rust and Jake Guentzel, both drafted in the third round. Pittsburgh has made the playoffs in 12 straight seasons, but there was no shortage of change along the way, often the consequence of a top contender occasionally falling short.

“In Pittsburgh over those nine years, we may have won three times, but the roster got flipped a few times and a few coaches and a few GMs,” said forward Chris Kunitz, who played on all three of those Cup-winning Penguins teams. “People look at the number and say it was a success, and every time we were there, they were trying to put a team on the ice to win a Stanley Cup. It wasn’t just to get to the playoffs, and expectations were high. Those years you didn’t win were disappointments, and I think there’s a certain echelon of teams that that’s their expectation and that’s their goal. If you didn’t finish it like that in the end, it wasn’t looked upon very kindly and there was changes to be made.”

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The Capitals have joined the Penguins in that echelon of expectation, and they now hope to model similar Cup-winning results. That means making the most of this window with Ovechkin, Backstrom and Holtby before worrying too much about the next one.

“The decisions for us are immediate,” MacLellan said. “You’re still looking to the future with Vrana and these guys, but we need to do the best with the team we have right now for those guys.”