The league ruled that Chiarelli could not counsel the Bruins on any of the Ottawa Senators free agents in July 2006. Chiarelli had just been hired away from the Sens, and Chara, who was unrestricted at the time, had just concluded his third season in the Canadian capital.
However it came about, Chara was one of the first signings of the Chiarelli era in Boston. Late Friday night after the Bruins clinched their first trip to the Stanley Cup Final in 21 years with a 1-0 victory over the Tampa Bay Lightning in Game 7 of the Eastern Conference final, the two men who have seen Boston evolve from an also-ran to contender shared a moment in the Coors Light-soaked locker room.
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"Obviously, we've been together [for two] tenures," Chiarelli told reporters at TD Garden on Saturday. "We went to one conference final with Ottawa and lost [in 2003]. We just kind of connected briefly after last night's game and I could see a little bit of a twinkle in his eye. And it was kind of a special moment for me to share that moment with him. I can't say enough about him as a player."
Chara, the Bruins captain who has one Norris Trophy to his credit and is a finalist again this season for the award that goes to the NHL's top defenseman, anchored a blue line that shut down the high-powered Lightning in Game 7. Next up are the Sedin twins, Ryan Kesler and the rest of the Vancouver Canucks as the Stanley Cup Final begins on Wednesday.
Patience and stability have been a hallmark of Chiarelli's term in Boston, especially after coach Claude Julien was hired before the 2007-08 season. As other teams in town were winning titles, the Bruins failed to advance past the second round of the playoffs. Those lackluster endings included last season's collapse against the Philadelphia Flyers despite a 3-0 series lead.
That doesn't mean Chiarelli stood pat as his moves in the weeks after that flameout likely were the difference in the seven-game series.
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"He's been obviously great in playoffs," Chiarelli said. "He's got a few game-winners, but he's just doing what's natural for him: using his size and strength and going to the net and creating room for other players. We are very happy for him. It's his first playoffs experience and he's doing extremely well."
Horton's conference semis were marred when he was caught on video squirting a fan with a water bottle after Game 6 in Tampa, which, Chiarelli said Saturday, drew a fine from the league. Of course, most was forgotten when he put the puck past Lightning goalie Dwayne Roloson in the closing minutes on Friday.
Then there were the in-season acquisitions, which include forwards Chris Kelly (Ottawa) and Rich Peverley (Atlanta) -- acquired largely to replace the lost production after Marc Savard went down for the season, and possibly his career, with a concussion in January -- and defenseman Tomas Kaberle (Toronto).
Kelly, one of only four Bruins players who have played in a Stanley Cup Final previously, had four assists in the conference finals and 11 points through the first three rounds. Peverley logged an empty-net goal in Game 5 and had eight points in the playoffs.
"You saw both Rich and Kelly on the ice in the last shift of the game," Chiarelli said. "They are both very reliable players. Peverley can back the D up with his speed and his moves, we needed some of that. When we lost Savard, he was hard to replace. We had to bring in a couple of things to bolster our forward lineup."
The Kaberle trade hasn't worked out quite so well and it became more costly on Friday. He was acquired before the deadline from the Maple Leafs in exchange for former first-rounder Joe Colborne and two picks: a first-round selection and a conditional pick. That "conditional" tag, however, was removed when the Bruins' advanced to the Finals, meaning they will also have to fork over their second-round pick in next year's draft.
Kaberle hasn't been the force on the blue line that was expected and his shaky play has led directly to some costly goals. He does have eight points (all assists) and is a plus-7 in the postseason, but that has done little to satiate the fans in Boston who have taken to booing Kaberle at times.
"Yes, he has been under heat, but what he's added to the team is something that we didn't have and something that was hard to find," Chiarelli said. "[It's] almost impossible to find at the trade deadline and that's the ability to make strong plays with the puck offensively. That's the ability to skate into a trap like we saw this past series."
Then there's the trade Chiarelli needs credit for not making: dealing goalie Tim Thomas. Thomas didn't play a minute last season as the Bruins stuck with Tuukka Rask. Thomas, one of the league's highest paid goalies who made $6 million this season, was the subject of trade and entered the season with a white mask -- a color that would fit in wherever he was dealt.
Then Thomas began on a hot streak that lasted the entire season after undergoing offseason hip surgery. He went 35-11-9 and his save percentage (.938) was the best since the statistic was first tracked in 1976-77. He's the odds-on to win his second Vezina Trophy and he shut out the Lightning twice in the conference finals.
"You just saw he wanted to make amends for having a not so great season last year," Bruins forward Milan Lucic said. "He is definitely going to win a Vezina his year. He has been our best player from the start of the year. Hats off to Timmy [for] playing as good as he has. He is just going to have to keep doing what he is doing. We are all happy and excited about what we have done today, but there is still more that needs to be done."