Can the Cup champion Capitals keep the band together?

The Capitals had a special chemistry that led to the franchise's first Stanley Cup. But with the pending free agency of John Carlson, left, it's unclear whether they'll be able to replicate it as they defend the title in 2018-19. Bruce Bennett/Getty Images

Watching the Washington Capitals parade around with the Stanley Cup was Don Fishman's dream. It's what he thought about as a young man watching Rod Langway patrol the ice at the Cap Centre. It's what he pondered as he watched Olaf Kolzig deflect pucks when the franchise made its only previous Cup Final. It's what he couldn't believe happened during Game 5 in Las Vegas, when Fishman quickly changed out of his Capitals jersey into a suit and made his way down to the ice to join the team's other executives in celebration.

"I always hoped to see it, but I never really planned on it," Fishman said.

It was a dream he helped turn into reality. As the team's assistant general manager, director of legal affairs and resident capologist, Fishman will help determine if that dream extends through next season and beyond.

Fishman is in his 13th season with the Capitals, hired by former general manager George McPhee just as the NHL implemented the salary cap in 2005.

"I love the cap. First, it gives me my job," he told ESPN with a laugh. "I was thinking about that yesterday. I was brought on board in 2005 when the cap first started. It benefited so many organizations, and we were one of them: It gave us a chance to compete for a Stanley Cup. Not just compete to be competitive, but compete to win it all.

"There are probably 20 or so teams that want to spend to the cap and try to win the Stanley Cup, and that's pretty cool for sports. I'm a fan of other sports too, and I'm not sure you can say that about other sports. Everyone wants to be able to go into a season saying they have a shot at the title, and I think we have the best parity of any sport."

But there's another side to the salary cap's ample parity, which is that great teams are eventually forced to shed talent as their success inflates salaries.

"An agent said something similar to me about a month ago, saying you must not like the cap, or having to give up these players. But I never think about it that way. It's just the system we live in," Fishman said. "We had to go through something like that last summer. Our team got worse on paper because we ended up paying the players we kept more money. We re-signed T.J. Oshie. We re-signed Evgeny Kuznetsov. We re-signed Dmitry Orlov and Andre Burakovsky. That's life. We made our bets on those players, and as it turns out, we made some good decisions."

The wagering window is almost open for the Capitals in their attempt to defend their title. The first bet to either make or pass on? Defenseman John Carlson.

The Carlson Conundrum

As one would expect in a contract year, Carlson had his best career numbers for the Capitals. His 68 points led all Washington defensemen and made him the team's fourth-leading scorer. His 15 goals were two off the NHL lead for defensemen. He skated 24:47 per game, and that number jumped to 25:38 in the playoffs, in which Carlson had 20 points in 24 games.

"I thought he had an outstanding year. Played great in the playoffs," said general manager Brian MacLellan. "I'd really like to have him back on the team."

But that's the trick, isn't it? Carlson is an unrestricted free agent, and by far the biggest prize this summer among UFA defensemen. The 28-year-old could command a contract in the neighborhood of $8 million annually.

The Capitals and Carlson's agent agreed to let the season play out and then pick up negotiations in late June.

"We'll see what happens. We'll talk and go from there. I don't really know what else to say other than that," Carlson said. "I love it here and all that. I want to stay here. But there's more to it than that."

Like, for example, the Capitals' cap considerations. Cap Friendly has the Stanley Cup champions with just over $11.2 million in cap space for next season. That's with top-line forward Tom Wilson and playoff hero Devante Smith-Pelly as restricted free agents, and Carlson's defensive partner Michal Kempny as a UFA as well.

"We're going to be limited, to a certain extent, with what can offer. But hopefully we can find a spot that satisfies both parties," said MacLellan.

This is where Fishman comes in. He said the groundwork for a contract offer for a player like Carlson is something "a year to a year and a half" in the works.

"You want to look at the cap year to year, and so when we're doing contracts that extend for three or four years, we want to look at the contract that might come up in that term," he said. "So we're always looking at what a player might earn [on future deals]. I'm constantly doing valuations on players and what they might be worth. I'm constantly looking at comparables.

"My goal is never to get a home run deal on a player. My goal is find out the true valuation of a player so I can advise my boss and our president and owner going into the negotiation. So if they want to overpay, they can overpay, but here is what a reasonable evaluation is going to be."

Sometimes, overpaying at the time is worth it in the long run.

Such was the case with Alex Ovechkin.

The Ovechkin Contract

Capitals owner Ted Leonsis will forever remember the phone call he received when it was announced that Ovechkin, then 22, had been handed a 13-year, $124 million contract by the team. It was the first NHL contract that crested over the nine-digit threshold.

It was a call from NBA commissioner David Stern, with whom Leonsis was acquainted through his ownership of the Washington Wizards. "[He said] boy, you are going to live to regret this," Leonsis would tell the Washington Post. "I thought you were a smart guy, and that's the stupidest thing I've ever seen."

He wasn't alone in thinking that. At the time, the $9.538 million salary cap hit was seen as massive, far beyond any that had been established in the previous three seasons. In the years that followed, the Ovechkin contract was seen as shortsighted: By 2010, the "back-diving" contract was en vogue in the NHL. By the last year of his 13-year deal, Duncan Keith was set to make $1.5 million in base salary, helping to bring his overall cap hit down to $5,538,462. The last two years of Roberto Luongo's 12-year deal paid him $1 million, bringing his hit down to $5,333,333. And so on.

Fishman said the Capitals considered that creative accounting for Ovechkin.

"I remember talking about that concept with George, but I think Ted and [team president Dick Patrick] wanted to do a straight contract on valuation and not go that route. Which was fine. We didn't really entertain it. We wanted to value it with what it was worth," Fishman said.

There were years in which the Ovechkin contract weighed more heavily on the Capitals' cap than in others.

"It kind of goes to the arc of our team," Fishman said. "As more and more of our good players needed new contracts, there probably were a few years where we were hamstrung by a $9.5 million player. But Ovi's been amazing. He's probably had three different renaissances during his contract."

Ultimately, the value of Ovechkin's contract went beyond the dollars.

"I was so happy with that contract because it was a statement about the team and the city," Fishman said. "I'll always thank Ovi for making that commitment to the organization. No matter what you want to say about the valuation, it was an important moment. We weren't a hockey town yet. We weren't on the map of the hockey world. And people were saying he was going to go to Montreal or to New York. For Ovi to say he was going to commit to Washington for 13 years was such a statement. I always hoped it would lead to a Cup, but I wasn't sure. It was a really great statement for Ovi. And then not long after that, [Nicklas] Backstrom committed for 10 years."

And they were both still on those contracts in Game 5 of the Stanley Cup Final, when Ovechkin passed the Cup to Backstrom.

"This is what we wanted the whole time. So finally we're there and we're so happy about this," Backstrom said after Game 5.

Keeping The Band Together

Literally and figuratively, the Capitals' Stanley Cup victory has been intoxicating.

But after all the keg stands and public fountain snow angels and echoing profanity on the National Mall have ended, the Capitals have immediate considerations for next season's team: whether, or how much, to compensate good soldiers (Jay Beagle, Tom Wilson) and relative newbies who starred in the playoffs (Smith-Pelly, Kempny) and one absolute standout (Carlson) who have reached free agency.

The year after that, it's young Andre Burakovsky and Jakub Vrana that need contracts. The summer of 2020 means new deals for Backstrom and Braden Holtby. The summer of 2021? Well, that's Ovechkin's next contract.

It's Fishman's job to plan for all of this, but it's also his job to be a reality check for MacLellan in figuring out the Capitals' future.

"I'm a lawyer. I love still being a lawyer. And your job as a lawyer, I found out at a young age, is to deliver bad news. So I don't mind delivering it," he said. "But it's usually not being a killjoy. It's just delivering bad news. Like, 'I know you think this player's valuation is X, but it's actually Y, so if you want this player, you're going to be paying him Y.'"

To that end, he doesn't believe that the Capitals will overcompensate those players who helped them win the first Stanley Cup in franchise history.

"I can't speak for other organizations, but I don't think that'll be the case with ours," he said. "Mac's a really good judge of talent. Mac's pretty levelheaded about these things. We're going to give a fair valuation of our players."

The Capitals aren't afraid to spend on talent. Despite the youth movement on the roster that helped change the vibe of this year's club, Washington was still a team that spent to the cap in 2017-18. By the end of the summer, the Capitals could face another salary-cap nightmare. Fishman believes that the way teams face that nightmare can determine Stanley Cup dreams.

"It's funny how it works. At the deadline this year, we didn't have enough space to add a [player like] Kevin Shattenkirk, but we had barely enough money to add Michael Kempny, and that turned out be a wonderful addition to our organization," he said.

"You never know."