Peter Chiarelli has made a lot of trades, none better than acquiring Dennis Seidenberg

Upon his arrival in the summer of 2006, General Manager Peter Chiarelli walked into the Bruins’ organization with a handful of key players already in place for a good playoff team. But in order to make that club a Stanley Cup contender — and eventual winner — Chiarelli’s bold moves, along with a ‘I’m going it my way’ approach along the way turned this once bottom-of-the-barrel hockey club, into NHL Champs.

Patrice Bergeron, David Krejci, and now Conn Smythe winner Tim Thomas were all products of the Mike O’Connell regime. While key forwards such as Milan Lucic, Brad Marchand (both drafted in the same class of ’06) and Captain defenseman Zdeno Chara were all added by then-interim GM, Jeff Gorton.

But that’s not to say that the Harvard graduate has a Cup contender handed to him on silver platter, no-no-no. Chiarelli, and the minds of the Bruins brass, wheeled-and-dealed his way to the promise land after the club’s 39-year drought. Some good, some not-so-good.

We look back at the times when we scratched our heads and said to ourselves, ‘what the heck?’ to some moves. One that stands-out as clear as high noon was when the GM traded for a no-name college defenseman named Steven Kampfer — on the eve of the 2009-10 NHL trade deadline — from the Anaheim Ducks for a fourth-round draft pick. Although the Bruins needed immediate, instant help on their playoff-bound team, Chiarelli clearly saw the potential in the Michigan native, as Kampfer proved to be a serviceable defenseman for close to half of the regular season this year.

Although that particular trade did zip for that ’09-10 club, keeping one hand on the current prize and another on the future proved to be an attribute that, at the time, was well overlooked.

One trade in particular that was not so good, in hindsight, that I’m sure Chiarelli would like to have back was in 2007, when he did business with the Chicago Blackhawks, swapping forwards Kris Versteeg for Brandon Bochenski. Bochenski had a couple of cups of coffee with the Bruins, continued his journey throughout the NHL/AHL, and eventually wound up in the Kontinental Hockey League (KHL).

Chiarelli was active. He’s been juggling draft picks, prospects, former first-round picks, and future considerations for the betterment of the team since Day 1.

One move that still deserves high praises and high-five’s up-and-down Causeway St. was the infamous Phil Kessel trade in September, 2009 — a saga that seemed to have lasted an eternity. The GM handed the former first-round pick (by Gorton) to the Toronto Maple Leafs in exchange for a whole lot of great draft picks; landing both Tyler Seguin and Jared Knight in the 2010 NHL entry draft.

But with all of those trades, none compares to the one that transpired on the trade deadline last year, March 3, 2010. While Chiarelli was making “minor” moves for small pieces earlier on, those components would soon be flipped into the kingpin of all Bruins’ trades in his regime.

(Photo: Bridget Samuels) Seidneberg was the playoffs leader in TOI and blocked shots

The crafty GM committed grand larceny against the Florida Panthers when he shipped their second-round pick in the 2010 NHL Draft (they still had Toronto’s second-round pick) plus rugged winger Byron Bitz (who played just seven NHL games this past year) and Craig Weller (who came to Boston earlier on last season, along with a second-round pick in 2011 and Alexander Fallstrom for forward Chuck Kobasew). In return they received prospect blueliner Matt Bartkowski and, arguably, the Bruins No. 2 Conn Smythe winner of this year’s playoffs, Dennis Seidenberg.

Chiarelli’s offseason move, this past June, also from Florida, that landed him Nathan Horton and Gregory Campbell was spectacular. But at the end of the day, acquiring Seidenberg was arguably the best move of the GM’s tenure.

“The deals that we made, really it started for me when we got Dennis Seidenberg,” said the GM today during his press conference to the media. “We had to be fairly aggressive with that deal for a couple of reasons.

“He’s a very strong, he’s like a bull on the boards with the puck. He’s a strong skater.”

A freak accident against the Maple Leafs at the end of the 2009-10 NHL regular season left Seidenberg with a lacerated tendon in his forearm, causing the hulking defenseman to shut it down early, missing the entire post season.  But Seidenberg shined throughout the post season this year, becoming a pivotal player on the backend — particularly when he moved up to the No. 2 role after Game 2 of the first round against Montreal, skating alongside Zdeno Chara and instantly becoming the best shutdown tandem in the NHL.

“And you know we obviously had him in the playoffs  but he was obviously a big part of our team this year,” Chiarelli said. “We got him for shutdown capabilities and we got him to play with Zee [Zdeno Chara]. Now we wanted to spread the wealth and that was what we did throughout the year.

“You talk about critical junctures in this playoff run and when we decided to pair him up and give him considerable minutes with Zee after game two,” the GM recollected. “You can see him just take off. I mean he had a very good year, but you can see him take off with confidence. And I mean he had a terrific, terrific playoff. And I can count, I don’t think there was two or three times that he made a real blunder.”

Seidenberg still pitched-in offensively with 1-10-11 totals and a plus-12 rating. He made some flashy yet bold moves on the blueline, taking chances by pinching the puck in to create offense — especially in the second round against Philadelphia.

The 6-foot-1 Seidenberg was just simply a tank in the playoffs. He topped the NHL charts with over 690 minutes of total ice time played and 74 blocked shots, and his 57 hits were fifth among all defensemen.  Good thing he’s in the fold for a few more years.

“I don’t know if he ever lost a battle, well he lost a few, I might be overstating. When he went in you knew the other guy was going to be in for a big time battle. He was great at picking pucks off the boards

(Photo: Steve Babineau/Getty Images)

with his feet.” Chiarelli added. “And the ability to make the passes he makes on his backhand on his off-side is, those are hard passes to make, really hard passes to make when you’re under pressure on the blue line, his hard rings on the breakouts on the backhand.”

There’s no doubting the Horton and Campbell trade was enormous. And there’s no doubting that the Bruins wouldn’t have won those overtime games if it wasn’t due in large part to Horton.

And the acquisitions of Chris Kelly, Rich Peverley, and Tomas kaberle need not be overlooked, as the trio each played their respective roles and were enormous additions to Chiarelli’s trade-list and Stanley Cup winning team.

But for the things that you don’t notice on the ice, and for those that you do, Charelli hit the jackpot with Seideneberg.