The one thing you cannot say about Chiarelli is that he was indecisive. He never met a blockbuster trade he didn’t like.
And that, more than anything, is what got him into trouble. His many good moves were followed up by equally bad ones, sometimes with the same player.
And
Tyler Seguin is a prime example of that unfortunate juxtaposition. Unable to sign his top scorer in 2009, Chiarelli traded
Phil Kessel to the Toronto Maple Leafs for picks that yielded the Bruins Seguin and Dougie Hamilton. Great, tenure-defining deal. But then Chiarelli botched it four years later when he dealt the immature Seguin to Dallas and got not enough in return, while Seguin flourished in Dallas into the type of go-to offensive player the Bruins were so desperately missing this season.
Chris Kelly for a second-round pick? Terrific. Signing a 31-year-old Kelly to a four-year contract extension at $3 million per season? Not so much. Drafting
Milan Lucic 50th overall and
Brad Marchand 21 picks later in his first draft as Bruins GM was brilliant. Three years at $18 million for Lucic clearly was not. Getting
Johnny Boychuk for
Matt Hendricks in 2008, genius. Trading him to the New York Islanders for a couple of draft picks, then watching your team’s defense corps ravaged by injury and a lack of depth, both reprehensible and unfortunate.
This was a guy who signed
Marc Savard and
Zdeno Chara and traded for
Dennis Seidenberg,
Adam McQuaid,
Mark Recchi and
Tuukka Rask. Every one of those was a ridiculously lopsided trade in favor of the Bruins.
But the Bruins had become an old, slow team that seemed to have trouble keeping up with their opponents who could move their feet and the puck quickly.