People love to talk about how great a trader Peter Chiarelli was for the Bruins but if you actually go back and look, he has a very checkered history.
Trades collected from:
http://www.nhltradetracker.com/user/trade_list_by_team/Boston_Bruins/1
In order with who the Bruins received on the left.
1st year:
1) Chistov for a 2008 3rd round pick (non-NHLer) - (seems like Rinaldo for 3rd to me)
2) Sauve for Redenbach - (a wash)
3) Unfulfilled Future Considerations for Wade Brookbank - (can't remember if this was salary dump but likely so)
4) 5th round (Denis Reul) for Yan Stastny - (a wash)
5) 4th round (about to be traded) for Jurcina - (I liked Jurcina but a wash)
6) Bochenski for Versteeg - (a major blunder)
7) Ference and Kobasew for Primeau, Brad Stuart, and that 4th from above (TJ Brodie was picked) - (part salary dump but also the start of the traded picks becoming great players trend that haunts Chiarelli - I'd call this a loss)
8) Aaron Ward for Paul Mara - (a wash)
9) Wideman for Boyes - (I think a loss as Boyes was an awesome winger for Bergeron but most consider a wash)
10) McQuaid (3 years before he plays 1st NHL game) for 5th round pick (Jamie Benn - 2 years before he plays 1st NHL game) - (a loss - Crazy when you realize Dallas got their top 2 players from Boston thanks to Chiarelli.)
That concludes the 1st season of Chiarelli trades.
He did get 2 defenseman that would help the Bruins win a cup 3 years later but in doing so he gave up a better defenseman (Brad Stuart) along with wingers Versteeg (2 cups) and Boyes (40 goal scorer), and 2 picks that would become TJ Brodie (top 4 D) and Jamie Benn (another 40 goal scorer).
He was a prolific trader who lost almost all his trades this 1st year including giving up 2 40 goal scoring wingers.
2nd year:
1) 6th round for 6th round - (a wash as both non-NHLers)
2) 2nd (Cross) for 2nd and 3rd - (a wash as all 3 are non-NHLers)
3) Fernandez for Kalus and 4th (Fallstrom) - (a win, Fernandez had a good, final NHL year with the Bruins)
4) Schaefer for Donovan - (a wash)
5) Soderberg for Toivonen - (a win as Soderberg is a quality 3rd line C)
6) Nokelainen for Walter and 2nd - (a wash)
7) Saunders and Skinner for Mowers - (a wash)
8) Auld for DiCasmirro and 5th - (another short term goalie win as Auld had a good year for Boston)
9) Hnidy and 6th (Tremblay) for Bochenski - (a win as Hnidy would have a good season and a half for the Bruins before leaving for MN--came back for 6 games during the cup run but that is not a result of this trade)
That's the end of the 2nd season as GM of the Bruins. Chiarelli got much better at trading as he didn't lose any and did get some short term wins. This is where Don Sweeney now sits entering his 3rd season as GM. It's tough to compare what Sweeney gave up and got back in return (picks) as we have to see if they turn into NHLers but so far it does not look as bad as Chiarelli in his first couple of years.
Chiarelli's lauded NHL pro scout trading skills happened much later as we get closer to the cup year. His early trading years strategy seemed to be to just throw as many darts on the board as you can and see what sticks. This was fairly disaterous that 1st year, somewhat neutral in the 2nd, and gets better starting in the 3rd year when he gets Recchi, Paille, and Seidenberg--however he also traded Ward for Eaves and immediately bought Eaves out while also being forced to trade Kessel in what seemed like a loss but turned into a win down the road as Toronto tanked.