The two second round picks are the Philadelphia Flyers' second round pick in the 2015 NHL Entry Draft (acquired by the Isles in a March 4, 2014 Andrew MacDonald trade) and the Islanders' second round pick in the 2016 NHL Entry Draft.
The Bruins would acquire the conditional 2015 third round pick from the Isles if New York trades Boychuk during the 2014-15 season to an Eastern Conference team.
Prior to the Bruins' final preseason game against Detroit on Saturday, Chiarelli addressed media at TD Garden regarding the transaction.
"This is a tough trade," said Chiarelli, stating what the gathered reporters in front of him already knew. "We all like Johnny."
"I spoke with him shortly after the trade consummated. I told him, 'you know, Johnny we brought you here from Colorado, you did everything we told you to do. You got better as a player. You were patient, you got better, you were part of the fabric of the team and this was really hard to do, but we've got - there's an element of business to it, an element of hockey and we tried to get ahead of it a little bit.'"
"So he was upset, I was upset, I'm still upset."
The fact that it was a difficult trade to pull the trigger on goes without saying.
"This deal was born out of couple things: one, our cap situation, two, as I said, trying to be proactive on team planning," said Chiarelli. "I look at this a little bit globally. This may be one in the series of two or three steps throughout the course of the year, and I wish I could do everything at once."
"We were involved in some deals for players and as I said to you back in June or July - this is stuff that we have to peck away at and unfortunately, this is the type of stuff that comes first."
"I feel we got very valuable return - those are real valuable picks that can be used to draft players or to acquire players."
The Bruins had a surplus on defense, with nine able bodies, including the arguably NHL-ready David Warsofsky, who was placed on waivers Saturday, for the purpose of assignment to Providence.
Boychuk wasn't expendable, and he will be missed. The blueliner was set to become an unrestricted free agent at the end of the 2014-15 season, when his current three-year deal came to an end.
His salary carries an annual cap hit of $3,366,667.
"Obviously we're in a much better spot than where we were," said Chiarelli, in terms of getting under the $69 million salary cap prior to submitting their opening night roster by 5:00 p.m. ET on October 7.
The cap situation was only one factor among many. When Boychuk's deal is done, he will command significantly more on the open market. Prior to the trade, the Bruins had not tried to work out an extension with Boychuk.
"You know what, it was both [factors], and I'm not going to put a number on it. Part of my job is projecting the market and I see where Johnny's market's going and all the strength to him," said Chiarelli. "He's earned it. He battles and he's a good player - he's earned it, so part of it was that."
"Part of it was doing some housekeeping for our cap issues, and part of it was the strength of the return - strong return. So you look at those three things and you make a decision to move forward."
"How does it impact our team? He's very well-liked and I'm sure the guys are bummed and they're probably a little bit bummed at me for doing it, but you know, it's about making the team better now, tomorrow, the next day, the next day."
Chiarelli knows the Bruins aren't as good right now, as they were the day before. It's the sacrifice that was made for long-term flexibility.
"Arguably this doesn't make us better now, obviously, but it's something that when I look at it in a series of steps, I think it's the right move," said the GM.
Boychuk was acquired by Chiarelli and the Bruins from Colorado in the June of 2008. He skated in 317 regular season games with Boston and 79 playoff games, including 25 en route to the Bruins' 2011 Stanley Cup Championship. He was a rugged mainstay on the blueline, logging top-3 minutes.
The GM was asked by a reporter about the short-term difficulty of trading away someone who could help make a run to the Cup this season.
"A lot of people have been saying that, but you're right, trading away a good player like Johnny, who plays No. 3 minutes and plays that second pair defending and shutdown, you're right," Chiarelli responded. "Now, having said that, we've got players that we feel that can fill - not with Johnny's shot, but with their skating or their strength. We're getting players back, so it's a tough call. He's a good man and he's a hard player, and you know, you have to make the call with taking into account the five or six factors that I went over."
"As far as the team, I feel good about the team. I think there's still areas where we can tweak and that's my job over the course of a shorter period of time - meaning I'd like to see how these guys look in 10, 15, 20 games. We’ve got some young players that are pushing, and we’ll see how that goes."
"It’s easy to say, ‘Let’s keep the team together, keep keeping the team together and it will subsequently be as we won four or five years ago, it will be the same team and we’ll win.’"
"Now, it doesn’t happen that way. Dynamics change, people change, the way they approach things change. And I’m not trying to keep refreshing, - it’s just that we want to get better and sometimes you can’t do it in one step. That’s how I see this."
Making tough trades, and tough decisions, is what comes with the territory.
The Bruins have been able to lock up core players like Patrice Bergeron, Tuukka Rask and David Krejci the past two offseasons. After the 2014-15 season, Reilly Smith, Torey Krug, Dougie Hamilton and Niklas Svedberg are all set to be restricted free agents. Five Bruins, including Carl Soderberg, will become UFAs.
"There's a list of priorities and part of my job is to prioritize," said Chiarelli. "And that's a little bit how it shakes out - I'd love to keep this team together, player to player, as long as I could, if I felt it was prudent on the hockey front and the financial front. And I've tried to keep the critical mass together and will continue to provide the right move for the organization."
"There's a lot of factors involved and you know, we could have kept [Boychuk] - we keep him, we're not trading him at the deadline; we keep him, we're using him. So that played in the factor too. You could say, 'here's what you would have gotten at the deadline,' but I don't weigh that as one of the factors here."
Amidst those factors the Bruins' brass weighed was their obvious defensive depth, though no player has Boychuk's armory.
"We've got guys who are going to step up," said Chiarelli. "You know, they're not the same player as Johnny [but] we've got players that are returning from injury - Adam McQuaid. We've got players that are coming into their own in Matt Bartkowski. We've got a player in Dougie Hamilton that's really picking it up. We've got Dennis Seidenberg coming back from injury, shaking the rust off - he was good [Friday[ night, he's getting better every day. We've got Zee who's trained in a terrific way this year, he's increased all of his performance metrics."
"So you have to rely on the other D picking up the slack and that was in our equation, as to what the other D would do."
Chiarelli had gone into training camp with the objective of mixing and matching the defensive pairs (along with the lines).
"And we went through that process and we came up with this," he said.
As far as defensemen taking on greater roles now, the GM was leaving that up to Head Coach Claude Julien.
"We've had discussions about and I feel he's got some tools in the toolbox," said Chiarelli. "And we'll see how the performance goes, we'll see how this first part of the season unfolds, but at the end of the day, he's got to decide."
While the defense is now coming into further view for the start of the 2014-15 season, there's still housekeeping to do up front.
The roster shaping will continue to take place before the opener on October 8, and into the regular season.
"[Next on the agenda is to] see how the team performs to start the season," said Chiarelli. "We have a couple of combinations and permutations that we can start our roster at on Monday, so you may see a couple of recalls."
Along with the trade, the Bruins announced Saturday that they placed Craig Cunningham and Jordan Caron on waivers. If they clear, the Bruins have the flexibility of 30 days, or 10 games, to freely move them up and down between Providence and Boston.
Once the roster's in place, the work isn't done. There could be an accompanying move with the trade.
"There might be," Chiarelli said. "A lot of things can happen. So there might be. You want to see how the team gells and gets together. There’s some new dynamics going on – new faces and some new dynamics, so you want to see how that goes."