By Matt Kalman, CBS Boston

BOSTON (CBS) — For the second time in one day Tuesday, Calgary defenseman Dougie Hamilton met the media wearing a hat from Mike’s Pastry in the North End.

“Do you get free cannolis for wearing that hat?” an esteemed media member asked Hamilton after he debriefed the surrounding horde.

“Of course,” Hamilton said.

One day of pastries at Mike’s might’ve satisfied Hamilton’s taste buds, but he surrendered the chance to chow down there for years to come when he reportedly forced the Bruins to trade him to the Flames on June 26, 2015 for draft picks.

The trade put the Bruins and Hamilton’s career on different tracks than they were on when the team and player were married. It’ll take years to determine if Hamilton or the Bruins will end up better off down the road. Hamilton’s decision to force a trade landed him in the midst of a rebuild and put the Bruins in pursuit of a young top-four defenseman who can be Zdeno Chara’s heir apparent.

The Bruins’ 2-1 win against Calgary on Tuesday highlighted how much losing Hamilton set them back and how far Calgary has to go to be a legitimate contender. It was an ugly affair decided on a late Patrice Bergeron power-play goal. Hamilton was minus-1 and the only noise he made came out of the fans, who booed him every time he touched the puck.

Hamilton didn’t mind the booing as much as he obviously minded living and playing in Boston.

“I don’t know, I kind of liked it. So it kept me going,” he said. “I don’t know. They’re obviously watching me out there and it means something to them. So it’s just motivation to me.”

The Flames have lost six in a row (0-5-1) and nine times in their past 10 games (1-8-1). They’re 26-33-4 on the season. The Bruins, for all their faults, are in third place in the Atlantic Division.

Although Hamilton has never publicly admitted he wanted out of Boston, general manager Don Sweeney made it clear the decision was the player’s when it came time to make a trade at the NHL Draft. The Bruins seemed willing to come close to matching the six-year, $5.75 million contract Hamilton signed with the Flames. But the story goes – as long as Hamilton won’t tell his side – that Hamilton made it clear money wasn’t going to be enough to keep him in Boston.

When the question was posed to Hamilton on Tuesday about regretting leaving, he didn’t deny his control over the matter. He also claimed to not have any regrets about being dealt to a team in a bigger rebuild than the Bruins’ reload.

“I mean we’re a young team and developing for the future and stuff. So you look at our core players, we’re all young players and only getting better. So we got to just keep developing as a team and keep improving and hopefully we can win a Cup one day,” Hamilton said.

The Stanley Cup, assuming that’s the one Hamilton was referring to, is quite far off from these Flames. Hamilton would’ve had a better chance at contending had he stayed in Boston as Chara’s partner and eventual replacement. But whatever he said prior to the draft sent Sweeney into a frenzy that resulted in a trade for three draft picks. Sweeney had the leverage because Hamilton was a restricted free agent with no arbitration rights. The GM could’ve made the player stay or hold out. Instead Sweeney opted to resolve the matter, even though that trade created a hole the Bruins might not fill for years.

That was no way for Hamilton to thank the organization that drafted him ninth in 2011 and groomed him to be the top-four or top-two defenseman he became. Still, Hamilton didn’t regret what he did to Boston.

“I enjoyed my time here and I’m thankful for all the opportunities and stuff. I developed a lot as a player and I guess in the three years I was here,” Hamilton said. “I learned a lot and everything. So just thankful for them and the opportunities they gave me and everything. So I’ve just got to think of that stuff and move on. I think I’m happy being a Flame now and it feels so far removed already. I guess it doesn’t really feel the same as earlier in the season when it was kind of fresher. I feel like I’m more part of the Flames now and enjoying myself.”

The Bruins are doing their best to make sure the Hamilton trade isn’t one they regret for eons. They used all three of their first-round draft picks last June, added an extra first-round pick the upcoming draft, and acquired Colin Miller in a trade. They might never find another Hamilton, but Hamilton’s development isn’t guaranteed to continue on an upward trajectory either. Nor are the Flames guaranteed to get any better than they are right now.

So far, the Hamilton trade was one that hurt both sides. Maybe the Bruins should’ve found a way to make Hamilton happy. Maybe the key was more cannolis.

Matt Kalman covers the Bruins for CBSBoston.com and also contributes to NHL.com and several other media outlets. Follow him on Twitter @TheBruinsBlog.

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