Boston had trailed 2-0 in the series before winning Games 3 and 4 at TD Garden to even the best-of-seven series. Chiarelli told his dad that night that the Bruins were going to win it all.
"I said that because there's too much resolve in the locker room," Chiarelli said Friday morning at the Garden. "You could just feel it, and at the end of the day, that's what happened."
It wasn't an easy road for the Bruins' ownership, management, coaching staff and players. Even at the start of the Stanley Cup playoffs, Chiarelli made a comment that he would consider the 2010-11 season a success if the Bruins were able to reach the Eastern Conference finals.
If Boston had failed, Chiarelli and coach Claude Julien would have been criticized, and their jobs could have been in jeopardy.
Now, they will always have their place in Boston sports history.
As GM, Chiarelli hasn't always made the right decisions. But in the past season and a half, he made critical transactions and molded this team into a solid mix of veterans and prospects, and it clearly worked.
"Everyone has a five-year plan, and so did we," Chiarelli said. "It's not like it fell exactly into place, but we were adding certain elements to get to this point. And it happened, so I'm a genius."
Chiarelli laughed after that comment, but there's no denying that he made all the right moves to shape this Cup-winning roster.
"Well, I guess there's an element of hope," Chiarelli said. "When you make deals, it's our job to be fairly confident that they're going to work out. If I go into a deal [with just a sense] of hope, then I usually don't make that deal."
It started with defenseman Dennis Seidenberg. Boston acquired the veteran blueliner via trade with the Florida Panthers on March 3, 2010. Almost immediately, Seidenberg made an impact, but he suffered a season-ending arm injury late in the season and missed the playoffs.
This season he played extremely well and was one of the better players in the postseason for Boston.
"Really it started for me when we got Dennis Seidenberg," Chiarelli said. "We had to be fairly aggressive with that deal for a couple of reasons. He was a big part of our team this year."
After another second-round exit in the playoffs in 2010, Chiarelli knew he had to be aggressive again and that the Bruins needed a highly talented forward. When Boston acquired Nathan Horton from the Panthers, it became an even better transaction because gritty forward Gregory Campbell also came in the deal.
"The Horton deal was obviously significant," Chiarelli said. "We felt like we had to be aggressive before the draft because there's a flurry of deals at the draft. He and [Seidenberg] are both big, strong players, and that was something we've always tried to have."
As the trade deadline approached this season, it was imperative for Chiarelli to make certain moves in order to add depth. The GM acquired veteran defenseman Tomas Kaberle and forwards Chris Kelly and Rich Peverley.
Chiarelli traded top prospect Joe Colborne, along with a 2011 first-round pick and a 2012 conditional pick in the second round, to the Toronto Maple Leafs in exchange for Kaberle. Sure, he did not entirely live up to expectations, but his play improved, especially in the Cup finals.
Boston landed Kelly from the Ottawa Senators for a 2011 second-round pick, but the Bruins had to give up a little more for Peverley, and sent forward Blake Wheeler and defenseman Mark Stuart to the Atlanta Thrashers.
"Seids, Horts, Pev, Chris Kelly and Kaberle were guys that we've always been targeting," Chiarelli said. "You can have a wish list, and it's just going out and executing and getting it. That was the hard part."
Chiarelli made all the right moves, and it paid dividends en route to the Stanley Cup title.
The Bruins are set moving forward into the offseason, and there won't be many issues Chiarelli will have to deal with. He wants to re-sign Kaberle, who, along with forward Michael Ryder and defenseman Shane Hnidy, is an unrestricted free agent. Forward Brad Marchand is the lone restricted free agent, and he is likely to receive a major pay raise for his heroics and success this season.
Winning the Cup, however, will have an affect on future deals.
"It's not easy making deals anyways," Chiarelli said. "I don't know if it's because we're an Original Six team, we're the Boston Bruins, and we've had good teams in the last two or three years and no one wants to help us. That's a natural reaction from other GMs.
"They're your colleagues, they're your friends, but they don't have to go out of their way to help you. I feel the same way. We're a very competitive group, so [winning the Cup] will only hurt it."
Now that Chiarelli and the Bruins have the winning blueprint, will he make a prediction for defending the team's title or its chances of a repeat?
"Holy cow," Chiarelli said when asked the question. "My charge is to win. So that's what I have to plan to do. We're in a good position and we've got a lot of the team under contract. We're in a good cap situation for once. We've got some young guys and we've got guys that are coming up. My job is to win, so we have to continue to keep that standard."
Joe McDonald covers the Bruins and the Red Sox for ESPNBoston.com.