The 1998-99 season was a landmark campaign for the Ottawa Senators. Following years of losing since rejoining the NHL in 1992, the Senators established franchise marks for wins (44) and points (103) before being swept in the opening round of the Stanley Cup Playoffs by the Buffalo Sabres.
It was a pivotal season for a young, up-and-coming club, but one that saw assistant general manager Ray Shero leave for the Nashville Predators. By season's end, general manager Rick Dudley left to join the Tampa Bay Lightning barely a year after taking the Ottawa job. Suddenly, the main front-office tasks fell on new general manager Marshall Johnston and his right-hand man, Trevor Timmins. Both men's backgrounds were in scouting, so the Senators decided to hire someone to help with legal and managerial tasks.
Their choice was 35-year-old Peter Chiarelli, an Ottawa native and agent/lawyer who today is among the NHL's premier GMs and on the cusp of winning his second Stanley Cup in three seasons with the Boston Bruins.
"We decided we needed somebody to come in and do contracts, look after the day-to-day business," Timmins told NHL.com. "That's how Peter got into this side of the business from the agent business. He was doing all the contract stuff, doing other legal stuff for the organization."
Chiarelli's was a prominent name in Ottawa before he joined his hometown team. His father, Frank, had starred on the hockey team at Rensselaer Polytechnic Institute, and his uncle, Bob, did the same at Clarkson University before serving in the Ontario legislative assembly and eventually becoming Ottawa's mayor. Another uncle, Jim, was the football coach at the University of Ottawa.
Prior to coming to the Senators, Chiarelli served as a player agent and practiced corporate commercial law with Ottawa-based agent Larry Kelly, demonstrating a knack for multitasking that would come in handy. A Harvard graduate who captained the school's hockey team, his college roommate was Mark Carney, who served as governor of the Bank of Canada before recently being named the first foreign head of the Bank of England.
"From Day One I think he was destined for management," Kelly told NHL.com. "He's got a tremendous background academically at Harvard. He knows the game and has a tremendous eye for talent, which is clearly displayed in the work he's done in Boston."
As Ottawa's director of legal affairs, Chiarelli made a wholesale career shift from representing players to signing them. On a small-market club forced to contend with a tight budget and small staff, he dove headfirst into his front-office education. That meant learning the finer points of scouting from Johnston and Timmins while honing his managerial skills alongside assistant GM Jarmo Kekalainen.
"He was with Larry Kelly and he was Harvard educated. We were impressed with all that right off the bat," said Kekalainen, now general manager of the Columbus Blue Jackets. "The thing I was impressed with was I thought he had good hockey knowledge. When he started putting in reports on players that needed to be signed, you could tell that he put a lot of thought into it and had a good eye for talent."
The Senators team Chiarelli joined featured some of the best young players in hockey, including Alexei Yashin, Vinny Prospal, Daniel Alfredsson and Marian Hossa. Chiarelli was tasked with retaining this young core, but his greatest contribution to the club may have been his role in a trade that would change the course of the franchise.
At the 2001 NHL Draft in Florida, the Senators traded Yashin to the New York Islanders in exchange for defenseman Zdeno Chara, forward Bill Muckalt and the Islanders' top pick, which at No. 2 was used to select center Jason Spezza. Chara and Spezza would emerge as stars and form the nucleus of a powerhouse team that won the Presidents' Trophy in 2003.
It was a deal that might not have been completed without Chiarelli.
"We were all bunking in a hotel room right through the night trying to get something done," said Timmins, who now works as the director of procurement and player development for the Montreal Canadiens. "I'm not a guy who can stay up all night. I need to get my beauty sleep and get ready for the draft. Peter was one of the troopers that pulled the all-nighter and hung in there in the GM suite in the hotel, being ready with all the contract information and aiding Marshall at that time.
"That's got to be one of the best trades the franchise ever made in Ottawa. It really turned things around."
Deals like that made Chiarelli a key component for the Senators. Working in one of the League's smallest markets, Chiarelli essentially was operating under a salary cap before the NHL formally installed one in 2005.
"We weren't even at the [cap] floor," said Jacques Martin, the former Senators coach who agreed that working within Ottawa's budgetary constraints prepared Chiarelli for the rigors of the salary cap. "It's a reality now of hockey. Because your star player takes on such a high percentage of your payroll, you need to have young kids on your fourth line or depth on defense to supplement your roster."
When Johnston retired in 2002, with Timmins and Kekalainen leaving around the same time, Chiarelli was named assistant GM under new general manager John Muckler. It was a unique opportunity that furthered his apprenticeship in Ottawa.
"That opened up a lot of opportunity for Peter," Timmins said. "John is a great guy, but he's not on the computer or does a lot of paperwork. He's really old-school that way. So Peter absorbed all that stuff. He evolved and probably gained his managerial skills having jumped into the fire."
In May 2006, weeks after finishing last in the Northeast Division with a 29-37-16 record, the Bruins named Chiarelli their new GM. His relationship with Chara proved fruitful when, in one of his first tasks as Boston's general manager, he signed the towering defenseman as a free agent. By 2011, Chiarelli's fingerprints were all over a Boston squad that, captained by Chara, captured the franchise's first Stanley Cup since 1972.
Two years later, Chiarelli's Bruins are back in the Stanley Cup Final.
"When you look at Peter, he went through a couple of general managers [in Ottawa]. He saw first-hand the evolution of our team," Martin said. "[He's a] Harvard graduate who learned the business right away and has been very successful, both through the draft and some great acquisitions. It's a mixture that has made their organization successful."