The following is an excerpt from "The Franchise: The Business of Building Winning Teams" Copyright @2024 by Craig Custance and reprinted with permission from Simon and Schuster. All rights reserved. Available on Oct. 15.

Brian MacLellan was walking through the lobby of the Eau Palm Beach Resort. Lumbering, really. He's a big fella. A Stanley Cup-winning NHL forward turned lawyer turned Stanley Cup-winning general manager, he's six foot three with catcher's-mitt hands. He worked his way up to the NHL through college hockey, not a typical path for a kid born in Guelph, Ontario. He developed under legendary college coach Ron Mason, scoring thirty-four goals as a freshman at Bowling Green. It was a total that would have led the team if his close friend George McPhee hadn't put up forty.

Hired as Capitals general manager in 2014, MacLellan is reserved but has a sneaky good sense of humor. When we exchanged texts the previous day to talk, it was the first conversation between us in nearly three years. He shot back: "Where have you been hiding?"

I explained. Asked to meet up. And here he was, walking through the lobby of this five-star Florida resort, underneath its crystal chandeliers and toward a terrace overlooking the Atlantic Ocean. Giant blue patio umbrellas provided shade to those stretching out on the blue-and-white-striped lounge chairs. The other guests around us were in bathing suits, enjoying the mix of waves crashing with the music being played by the pool. There was a hint of sunscreen in the air, plus the scent of what anyone walking by was drinking. We might have been the only ones in the area in slacks and polo shirts not on the hotel payroll.

I caught a break when MacLellan decided not to join his fellow GMs on the traditional Monday afternoon golf trip following the first full day of March's annual GM meetings. Instead, he was using the afternoon to recover from what had been a draining stretch on the job. I asked how he was holding up.

"Frustrated with our year, a lot of injuries, a lot of stuff," he said, settling in with his back facing the pool and the ocean. "It's been constant."

A few weeks earlier, Tarik El-Bashir wrote in The Athletic that MacLellan met with star Alex Ovechkin to loop him in on the Capitals trade deadline plans. Key players who helped Ovechkin break through in 2018 with his first Stanley Cup were most likely going to be traded, including Ovechkin's close friend Dmitry Orlov. MacLellan sent an email out to his fellow general managers to let them know the organization was open to moving its veterans and the sale was on. Orlov was the first to go. On February 23, the Capitals acquired three draft picks, including a first-rounder from the Bruins for the veteran defenseman. Five days later, Marcus Johansson was sent to the Minnesota Wild. That same day, MacLellan flipped the Bruins pick into young defenseman Rasmus Sandin in a trade with the Maple Leafs. Then the final move was a trade that sent Lars Eller to the Colorado Avalanche for another pick.

This was a series of transactions that ripped apart a former Cup winner.

It was Eller who dug a puck out from behind Marc-André Fleury and buried it home with 7:37 remaining in the third period of Game 5 of the 2018 Stanley Cup Final against the Vegas Golden Knights. The goal that sent a sea of red outside in Washington, D.C., into absolute bedlam. It ended up being the clincher. But when you talk to people inside the organization, that's not even the biggest goal he scored during that playoff run.

No game was more critical during the Capitals' run to the Stanley Cup than Game 3 of their opening-round series against the Columbus Blue Jackets. The Capitals dropped the first two games of that series at home. They probably should have lost the third game in Columbus. With the game tied at two and 1:16 remaining in regulation, Columbus star Artemi Panarin took a one-time feed from Zach Werenski and fired a shot off the left post, the ringing audible up in the press box. In overtime, Cam Atkinson banged one off the other post. These Blue Jackets seemed determined to bury the Capitals in a three-game deficit and put an end to it all, and probably change the future of the franchise dramatically. But with eleven minutes remaining in the second overtime, Brett Connolly fired a shot that Sergei Bobrovsky blocked, with the rebound bouncing to his left. Zach Werenski's clearing attempt was blocked by Lars Eller, and after a couple deflections somehow the puck found its way in. Just like that, the game was over. The Capitals were back in the series. If any of those Columbus shots had scored, the history of this franchise and those running it might be completely different. It's a perspective to keep in mind, just how much luck is part of the process when it comes to winning hockey championships.

"We talk about it all the time. All the time. Game 3 of the first round, we're about to go down three-oh to the Blue Jackets and who knows what happens after that if we get swept in the first round," said Zach Leonsis, son of owner Ted Leonsis and president of media and new enterprises with Monumental Sports. "Lars Eller comes back and scores the overtime winner and then we win every game after that [in the series] and we go on to win the Stanley Cup. It was inches away."

Inches. So yeah, trading Lars Eller hurt. Trading all of those players hurt.

"It wasn't easy," MacLellan said. "Plus, you get everyone to hate you, you know?"

This is the part of being a general manager people don't often see. The Capitals coaching staff was mad at MacLellan. They didn't care what the playoff percentage chances were at the time these deals were made, they were still trying to win games. Players were mad, too. Ovechkin's close friend was gone. The guy who scored a goal that changed a franchise and knit a group of players together for eternity was gone, too. These weren't just transactions, these were legacies leaving.

"You're ripping guys out of the room that you've won a Cup with," MacLellan said. "It rips the f -- ing heart out of the players, you know? They're like, 'What the f -- is going on?' They don't care about the future, retooling. 'Don't give me any of that f -- ing crap, it's my buddy you just got rid of.' ... You're calling guys and they're saying goodbye to everybody at practice."

The pain was still very real at this point. While you're winning with these players, you also get to know their families. You know the young kids. MacLellan understands there's a barrier between the players and management, but even that barrier only reaches so high. Become too detached and your humanity is lost. MacLellan's humanity is very much in place. In that moment in the Florida resort, it was clear the job was wearing on him. Building a Stanley Cup winner is way more fun than tearing one down. Even if you want to call it a retool or something much less gut-wrenching. I shared my theory that it should probably be a different general manager ultimately in charge of going through the rebuild than the one who won a Stanley Cup. He didn't disagree.

"You need new energy, you know?" he said. "I'm at a certain age where I'm going to be winding down here, too. I think my skill set was good for the stage we were at over the last ten years. It's probably better for someone fresh to come in at some point here. We've got to get through the next three years, see how we can do, and then it's new [when] Ovi's gone, all these guys are gone. The transition has to happen then, to a new guy. I think."

It was not an easy moment in time for the guy who helped build the first Stanley Cup-winning team in Capitals history. But that was not why I wanted to chat.

One of the things so admirable about the hockey community is how willing those who have had success are to help those still finding their way. It manifests itself in different forms. Sometimes it's an NHL coach running a penalty kill seminar during the summer for a group of youth coaches. Or Gordie Howe sharing advice with a young Wayne Gretzky on what it means to be an ambassador of the sport. Or Cammi Granato showing up at a Nike camp to give advice on winning in the Olympics to a group of women who grew up idolizing her.

Maybe it happens in different sports, but it definitely does in hockey. So when Kyle Dubas called Brian MacLellan to talk to him about how to persevere through crushing playoff disappointment, there was never any hesitation to share all he'd learned. And if anyone knew playoff disappointment and the criticism that follows, like Dubas was experiencing as the Leafs GM in 2021 after getting eliminated by the Canadiens, it was MacLellan and his Capitals.

In 2017, the Capitals suffered a Game 7 loss to the Pittsburgh Penguins that led to one of the most crushing postgame scenes I'd ever witnessed. It was the third consecutive second-round exit for a team that should have been a powerhouse. The media walked from player to player, looking for answers, when it was clear there weren't any. T. J. Oshie, covered in sweat, searched for words.

"You almost wonder how much disappointment you have to put yourself through before you can find a way to get the job done," Oshie said that night.

In that moment, I honestly thought we were seeing the end of the Capitals as we knew them. I'd find out later, there were players on that roster who felt strongly that dramatic change was the best path forward. MacLellan was the man charged with fixing years of underachieving in the playoffs by a team loaded with talent, and Dubas reached out to know what went into the decisions that followed.

"I went through our experience," MacLellan said. "The narrative is the same and we had the same type of teams where we had skilled teams. Really good during the season."

If a championship ring and years of distance had buried the frustrations that came with those underachieving teams, some of the emotion started to resurface as MacLellan recalled that era of helping lead the Capitals. Three consecutive postseason appearances were ended by the New York Rangers. After that, the rival Pittsburgh Penguins ended things in consecutive seasons. A team loaded with talent couldn't get out of the second round.

"It's like, 'Pittsburgh again? Right away?'" MacLellan said. "You make the argument we were the two best teams in the league. But you still got to get through it, you know?"

Like Dubas did after losing to the Canadiens in 2021, MacLellan guided the Capitals through soul-searching exit interviews following that Game 7 loss to the Penguins in 2017. He asked questions to get feedback, but he offered players a chance to vent their frustration. To get their anger out and express what they felt needed to be done.

Veteran defenseman Brooks Orpik was the first to go.

"It went by age," Orpik said when we chatted about those conversations.

In May of 2014, the Washington Capitals promoted MacLellan from assistant GM under McPhee to become McPhee's replacement. One of his first big moves was signing Orpik to a five-year deal worth $27.5 million, and it was a contract not universally applauded. On the day it was signed, a writer for CBS Sports concluded: "At that price, this deal is already looking like a bad one for the Capitals." The logic from those critical was that Orpik wasn't a great skater and was also starting to show his age. A tough combination. But to MacLellan, this was a deal made to start changing the culture of a team that needed to learn how to win. When he arrived, Orpik was very aware that the last thing teammates wanted was for him to come in and tell everyone how things were done in Pittsburgh. He wasn't about to share a bunch of Sidney Crosby leadership stories. But the Capitals players were curious. What made it work in Pittsburgh? How was Crosby as a leader?

The one area Orpik highlighted was practice habits.

"Sid is a guy who doesn't say a ton, but he is the hardest-working guy every single day in practice," he said. "With his stature, it forces everybody else to follow."

Working closely with coach Barry Trotz, Orpik tried to pick his spots in sharing some of that feedback and helping push the work ethic beyond what the Capitals were doing in the past. There was one point when the team got off to a slow start during the season that the two realized there was work to be done on this front.

"I remember saying, 'Hey, there's just so many things that have been done a certain way for so long, it's going to be tough to weed out some of these bad habits and cultural issues here that might be plaguing some of the success,'" Orpik said.

By the time the 2017 playoffs arrived, those issues had been ironed out. The players felt like this team was in its best position to win, and that's what made that Penguins loss so hard. For the player exit interviews, there were ten minutes slotted for each of the players to meet with MacLellan. When Orpik finished his conversation, he walked into the hallway, and there were at least five or six players in line waiting.

His conversation had lasted over an hour.

"Mac was really digging and probing," Orpik said. "I really want to win. I want to help Mac out because I want to win. But you're also not throwing anyone under the bus here. You're kind of caught. It's a tough wire you're walking on there."

"It was exhausting," MacLellan said.

When I pressed Orpik for details of the conversations, he paused.

"How honest was Mac?"

MacLellan certainly comes off as honest. He's direct in his answers and he's often direct when he's not willing to give an answer. In this case, he did both. According to MacLellan, two very clear solutions from the players emerged from those exit interviews. If he was going to follow the advice from his team during those lengthy conversations, they had two strong recommendations.

What were the two things?

"I'm not telling you," MacLellan answered. "It affects people. It's just a private thing. I'd be breaking a big trust thing because everybody opened up, one hundred percent."

Not only wasn't he sharing what those two things were, you can't even go back and look at transactions or moves MacLellan made that summer for clues. Management heard the recommendations from the players. They didn't do any of it.

"We chose to fight through those issues the next season," MacLellan said, "which could have been a disaster."

Orpik wasn't giving it up, either.

"I know what the two things were, kind of the collective response, and they did neither," he said before offering a question that marveled at the decision to ignore the two recommendations.

"Looking back even more, gathering all that information, how did they not pull the trigger on one of those things?"

Dick Patrick helped explain. He's been with the organization since 1982. He's the chairman of the entire organization. His grandfather was Lester Patrick, who won two Stanley Cups as a player with the Montreal Wanderers in 1905 and 1906 before going on to coach and manage the New York Rangers. His father, Muzz, won a Stanley Cup with the Rangers in 1940.

"Growing up as a boy, going with my dad to Rangers games, [I learned] the players are such good people, straightforward people. You can't be dishonest on the ice and be successful," Patrick said.

The most successful teams have that kind of honesty, he explained. There's also respect for each other, from the best player to the last guy on the roster to the team services person.

"A team doesn't win just because of one or two stars or the smartest coaching," he said. "It wins from having great effort and support and performance from everyone."

But to Patrick, there are limits to that honesty. Emotions cloud judgment. When you ask for an assessment coming off an emotionally draining series, the solution that emerges isn't always reasoned.

"First of all, players work so hard and put their everything into it every year. When you don't win, those exit interviews, they're not going to be happy. They're going to be very candid. Oftentimes it's 'This teammate has to go,'" Patrick said. "They work so hard at it. Everything is there to win. They never expect to lose when they're in a playoff series. When they do, they feel something went terribly wrong. What is it?"

In this case, they pointed in two directions. Neither taken by Capitals management. And the following season, the Capitals finally broke through and won a Stanley Cup, escaping the first round by a matter of inches. That's how perilous each decision is when running an NHL team.

"So I told Kyle that," MacLellan said. "Trust your instincts, do what you think needs to be done and not what the perception is. And if it's this serious, like our issues -- you assume he has [similar but] different things -- I said, 'You make the choice and live with it.' ... It's not what everybody else thinks. The players aren't always correct and the coaches aren't always correct and the fans definitely aren't always correct in their assessment. The media, the fans, the whole thing."

The trip to Florida didn't provide all the answers I was looking for. But it did open up new paths because it was clear there was a lot to learn from the Capitals and the battles they had to fight before winning a championship. Cycling through coaches. Moving on from George McPhee, who assembled the foundation of the Stanley Cup winners before being fired. Replacing him with his close friend.

There were fascinating choices made along the way in Washington, D.C., and the best place to get clarity was at the very top of the organization.