Sportsnet listed the three best (and three worst) deals that Chiarelli made in Boston:
http://www.sportsnet.ca/hockey/nhl/t...ves-in-boston/
The best is the Chara signing.
I don't remember the timeline, but according the post by opendoor earlier in this thread (
post #275), Chiarelli might not even deserve credit for the Chara signing. He had been hired by the Bruins, but was limited in how much involvement he could have with the team initially. Here's the original ESPN story on Chara's signing, and it only has a quote from Jeff Gorton, who was the Bruins' interim GM at the time:
http://sports.espn.go.com/nhl/news/story?id=2506763
Nothing from Chiarelli in there at all (which doesn't mean Chara didn't sign with the Bruins because of his familiarity with Chiarelli in Ottawa).
The second best is the Kessel trade. I'm always reluctant to give a GM too much credit for acquiring unknown draft picks.
All he got for Kessel was three future draft picks, with no idea of where they would fall in the draft. It was essentially slightly better than the compensation they would have received if Toronto had given Kessel an RFA Offer Sheet and Boston chose to not match it. For the deal Kessel signed, if it would have been an offer sheet, Boston would have received Toronto's first, second, and third round picks in 2010. If the Leafs would have offered a bigger contract to reduce the chances that Boston would match, it could have been Toronto's first, second, and third in 2010 plus their first in 2011.
Burke basically split the difference and gave up two firsts and a second, but made sure he owned the player's rights, rather than giving out an offer sheet that would have either overpaid the player or likely been matched.
Chiarelli got decent value for an RFA he was having trouble signing, but if Toronto had been a middle of the road or playoff team in those two seasons, he'd look a lot less like a genius if those picks turned into Jaden Schwartz and JT Miller instead of Seguin and Hamilton (and those are two of the better players taken in the mid-first in those drafts...they could have been a lot worse).
One interesting thing is that Boston had two top five draft picks in their system during Chiarelli's time there, and neither of them were still with the Bruins when their second contracts started. He is certainly not afraid to trade away young players.