Peter Chiarelli always searching for an extra edge

Only six NHL general managers have been on the job with their current teams longer than Peter Chiarelli’s tenure with the Bruins.AP

He studied economics in college and was trained for the law but much of what Peter Chiarelli does involves physics, operating in a place where time and space intersect, working in the future present while observing his hockey club both at ice level and from 30,000 feet and seeking that precarious equilibrium between stability and proactivity.

“I guess what I feel is, if you feel comfortable you’re not doing your job,” the Bruins general manager said. “You just want to keep pushing it.”

Chiarelli is in his ninth season on the job on Causeway Street, longer than all but half a dozen of his National Hockey League counterparts. Two summers ago he received a second four-year contract extension that will keep him at his post until 2018. It’s no coincidence that under his direction, the Bruins have made the playoffs seven consecutive times, their longest postseason stretch since their league-record 29 straight from 1968 through 1996.

“It’s a disappointment every year now if we don’t win the Cup,” said Chiarelli, who’s only the third Boston GM to have managed it along with Art Ross and Milt Schmidt. That’s how it is in Montreal and Chicago and Detroit and the other Original Six cities, where playing hockey in June is considered a civic birthright.

“I was watching a Red Sox game with Theo Epstein and Theo said to me, are you me in Toronto?” said Brian Burke, Calgary’s president of hockey operations and the Maple Leafs’ former president and general manager. “I said, I’m you times five. Hockey isn’t a sport up there, it’s a cult.”

Hockey in the Hub may be a bit less of an obsession but the annual expectations for the Bruins are at least as lofty as they are in the rest of the league’s hotbeds.

“Those teams get a lot of attention at playoff time,” said Tampa Bay general manager Steve Yzerman, the Hall of Famer who won three Cups as the Red Wings captain and another as a vice president. “They have a history of winning and a passionate fan base. Every fan is a GM.”

By the time Chiarelli’s contract ends, only Ross and Harry Sinden will have had a longer tenure. And while hockey is in his blood — his father Frank is a Rensselaer immortal and he himself captained Harvard’s varsity to the Frozen Four — Chiarelli didn’t set out to be a front-office fixture. But since he was hired to replace Mike O’Connell after the 2006 season, the 50-year-old Chiarelli has restored a floundering franchise to its former status as perennial title contender.

“Peter’s the best in the business right now,” said owner Jeremy Jacobs. “We’re relishing his success, his capacity. There’s not a day that I talk to him that he’s not in the midst of some mental exercise that has to do with this team. It’s fun to talk to somebody who loves the game like he loves it. You might know a doctor or a lawyer or a professional person who really lives that business and he’s that guy.”

Team player

Passion, preparation and probity are central to Chiarelli’s modus operandi. “Peter was not an overly-gifted player,” remembered former Harvard coach Bill Cleary. “He had to work for it. But the kids respected him because he was an honest hockey player.”

Chiarelli was part of the Crimson renaissance of the ’80s, a third-line wing who played alongside a couple of Hobey Baker award winners and several future NHLers, who spent time on the JV (“it was humbling”) but ended up with the “C” on his jersey.

“Peter was going to sacrifice for the greater good of the team,” recalled Lane MacDonald. “He always was going to put his teammates first ahead of himself. He had a humility that was endearing and made him a leader on that team.”

After graduation, Chiarelli dabbled in pro hockey with Nottingham in England before deciding to hang up his skates.

“I was playing and I was having some success but my heart wasn’t really in it,” he said. “That was the time when I started thinking about law school.”

Chiarelli got his degree from the University of Ottawa and practiced small-business law for three years before taking a job with agent Larry Kelly that provided him with a window into the mind of a GM.

“When you have to place players as an agent, you have to know where their needs are, where there are fits,” Chiarelli said. “There’s a lot of carryover from that part of being an agent to being a GM.”

After spending time on the sell side, Chiarelli moved over to the buy side in 1999 when he signed on as the Senators’ director of legal relations, which involved everything from contract research and negotiations to salary arbitration to player personnel decisions.

“He was good with the books,” remembered Carolina director of professional scouting Marshall Johnston, who was the Senators’ GM then. “In Ottawa we had a cap before the cap. You had so much money and that was it. Peter grasped that right away.”

Working with Johnston and then as assistant GM for successor John Muckler, Chiarelli received an advanced education in player procurement and development and in the art and science of roster management.

“John’s mandate was to win and he made some bold and aggressive moves,” Chiarelli said.

Familiar territory

His four years in Cambridge provided a useful observation point for what he could expect from the fandom when he took the Boston job in the wake of a losing season.

“I knew there was a high level of enthusiasm and feeling and sentiment toward the pro athletes here,” said Chiarelli. “When the Pats lost to the Bears in the Super Bowl, I was crushed. Billy Buckner, that was crushing, too. I remember watching that from my dorm room.”

When Chiarelli returned to the Hub two decades later, the Bruins had become teddy bears, with one playoff series victory in a dozen years, a DNQ following the lockout, and fans who’d forgotten what Lord Stanley’s chalice looked like.

“Peter had to get back here and immerse himself and get the pulse,” said assistant GM Don Sweeney, Chiarelli’s former Crimson teammate who wore the Spoked B for 15 seasons.

His re-entry was uncommonly awkward since the Senators, after a league mediation that Jacobs called “the meeting from hell,” were allowed to keep Chiarelli working for them until July.

“The way I came in was a little fractured,” recalled Chiarelli, who was at the Ottawa table at the draft when the Bruins chose Phil Kessel with the fifth overall pick in 2006. “It didn’t feel natural and that probably put me behind the 8-ball a little bit. There was a lot of organizational knowledge that I needed to get up to speed on that took some time.”

Meanwhile there was a coach to fire (Mike Sullivan), a coach to hire (Dave Lewis), free agents to sign (Zdeno Chara and Marc Savard), a front office to reconfigure, and a roster to revamp. When the Bruins finished with their most losses in a decade and missed the playoffs again and Chiarelli fired Lewis, the countdown clock on his own tenure began.

“This better be the right move,” Jacobs told Chiarelli when he brought in Claude Julien as the club’s sixth coach in eight years.

Though Julien had been dismissed by both Montreal and New Jersey, Chiarelli didn’t view it as a risky hire.

“It just goes to show you that you’ve got to scratch deeper than the surface on things,” said Chiarelli, who’d had Julien at the top of his list. “I felt pretty sure about Claude. He was someone that I had pegged from before, someone that I knew, someone that I liked as a coach and was comfortable with.”

Hiring Julien, which Chiarelli says was the best decision of his tenure, was a window into how he operates — due diligence, continuous communication, risk calculation, and decisiveness.

“I don’t think you can ever have enough information,” said Chiarelli, who believes that filtering data and judging character are his most notable skills. “It’s when you regurgitate it and keep going over it and it becomes circular and you end up coming back to the beginning. You just have to stick a fork in it and make your decision.”

Trading Kessel to Toronto and Tyler Seguin to Dallas simply were about improving the club.

“There’s a lot of calculation that goes into our moves and if it’s risky, I usually don’t do it,” Chiarelli said. “People may disagree but the level of risk to me hasn’t been that great. I don’t think risky moves are good. People say, your Kessel deal, your Seguin deal was risky. We don’t think so.”

Those moves were part of the continual evolution of the roster that’s necessary to keep a club with championship expectations in contention.

“Peter’s a real planner,” said Sweeney, who came in with Chiarelli as his director of player development. “He maps things out and adjusts as necessary.”

Dollars and sense

Those qualities are particularly important in the salary-cap era, when teams have to be pieced together by the numbers.

“You have to mind your p’s and q’s,” said club president Cam Neely. “A hundred thousand here, a hundred thousand there makes a difference at the end of it. You have to be pretty careful and mindful of that because you only have so much to play with. A bad contract here or there certainly handcuffs you down the road.”

What has helped is that Chiarelli and Julien are on the same page about where the Bruins are and where they’re headed.

“We’ve never really had a huge argument,” said Julien. “Fortunately for me, I guess, we see the game a lot the same way. It doesn’t mean we agree all the time but I think for the most part we see where each other’s ideas are coming from.”

That consensus comes from constant communication before, during and after the season.

“I try to make it a year-long process with Claude and his staff as far as giving them an idea where we’re going with things so we just don’t throw upon him: Here’s what we’re going to do tomorrow. I want to give them an idea of what we’re trying to do, where we’re trying to improve and where those areas may be. We’ve been through a lot, tough times and successful times, so we know what type of player it takes. We know what you have to do and it’s hard to get those players.”

It’s harder still to part with them, as Boston did with an estimable quartet after coming within one game of another Cup in 2013.

“We knew we had to because the cap was coming down and because we had some big-salary signings coming up,” Chiarelli said. “These were guys we had won with. We won with Nathan Horton, won with Tyler Seguin, won with Rich Peverley, won with Andrew Ference. We won with all those guys and then we either had to not sign or trade them. That summer was a hard summer.”

Smoother transition

Last summer was marked by decidedly less upheaval. After performing what Chiarelli called “a diagnosis and an autopsy” soon after the season ended, the front office concluded that the roster didn’t need a major overhaul.

“There are some tweaks here and there,” Chiarelli observed, “but this is a very good team.”

At its core were Chara, goalie Tuukka Rask, and centers Patrice Bergeron and David Krejci. All but Krejci already had been given lengthy and lucrative contract extensions and Chiarelli locked him in with six-year, $43.5 million deal.

“The Krejci move was terrific, keeping him in place and going forward,” said Jacobs.

That meant, though, that the Bruins couldn’t re-up Jarome Iginla, who left for Colorado and a three-year, $16 million offer.

Even as he was watching the preseason proceedings from ice level during the past few weeks, Chiarelli maintained his view from 30,000 feet. Six unrestricted free agents, including Carl Soderberg and Johnny Boychuk, will be free agents after the season. That affected for how much and for how long the Bruins would re-sign Torey Krug and Reilly Smith.

“When you’re building a team and building it within the confines of a salary cap, you have to make some tough decisions,” Chiarelli told season ticket-holders at the “State of the Bruins” town hall. “These guys are professionals and they know the whole team is not going to be kept together.”

What’s true on Causeway Street is true everywhere around the NHL, where Chiarelli has developed a reputation for being on top of his game.

“I’m deeply impressed with him,” said Burke. “The Bruins have won a championship. He’s drafted well. He hired a good coach. Whatever report card you give him, he looks like a kid who might get into Harvard.”

Chiarelli has spent enough time on both sides of the river to know that he works in a city whose residents expect a duck boat parade for one of their professional teams every year and he’s comfortable with the pressure that comes with assembling a championship ensemble.

“Over time, with experience, I’ve gotten to know that’s just one of the things of the job,” said Chiarelli. “It’s just something that you have to expect. My skin has gotten thicker. Sticking with your principles, I’m always going to do that. That’s just the way I am. I understand that sometimes people in this business lose jobs because of that but more often than not, if you’ve got good principles and good intuition you’re going to succeed.”