The Boston Bruins are among the NHL’s most storied franchises, boasting six Stanley Cup victories, tying them with the Chicago Blackhawks for fourth-most in league history. However, their trade history includes several deals that, in hindsight, have been less than favorable. While the Bruins right now are plagued with back-to-back losses, their history of decision-making with regards to trades is one for the books, but for all the wrong reasons.

In 2013, the Bruins made a significant move by trading Tyler Seguin to the Dallas Stars. Seguin, who had been selected second overall in the 2010 NHL Draft, was seen as a rising star. However, concerns about his maturity and off-ice behavior, coupled with a perceived underperformance during the 2013 Stanley Cup playoffs, led to the decision to trade him. The trade involved seven players: Seguin, Rich Peverley, and Ryan Button went to the Stars, while the Bruins received Loui Eriksson, Reilly Smith, Joe Morrow, and Matt Fraser. Post-trade, Seguin flourished in Dallas, becoming one of the league’s top scorers, while the players Boston acquired failed to make a lasting impact.

Further, the Bruins made a huge blunder after trading Canadian center Joe Thornton to the Sharks. The 45-year-old was traded for the trio of Marco Sturm, Brad Stuart, and Wayne Primeau. While Thornton was in the middle of a $20 million contract extension with the Bruins, they sent their star to the Sharks in return for three players.

However, Thornton went on to score 1,055 points in 1,104 games after the trade, something which Bruins fans still regret to this date. Only the likes of Sidney Crosby and Alexander Ovechkin have more points in that duration, denoting the significance of his performances. While these were some of the worst trades for the Bruins, Sweeney was also involved in a massive controversy after one of the trades.

It involved their young defenseman, Dougie Hamilton.

When the Boston Bruins’ GM justified his controversial trade

Back in 2015, the Bruins were involved in a massive controversy ahead of the 2015 NHL draft. They decided to trade their 22-year-old defenseman, Dougie Hamilton, to the Calgary Flames in exchange for three draft picks. This raised several eyebrows, especially because Hamilton was a key member of their lineup. However, the team’s general manager, Don Sweeney, later explained why they traded Hamilton ahead of the draft.

He revealed, “We extended Dougie a very significant contract offer. And it didn’t lead us to where we thought we’d be able to with him being comfortable being part of our group long-term. That sort of changed the course a little bit.” In another scenario, if they had decided to retain Hamilton, he would have been able to sign an offer sheet from another NHL team as a restricted free agent.

Although the Bruins weren’t afraid of that scenario, Sweeney felt that it was best to trade Hamilton for the three draft picks. While the Bruins remain one of the most successful teams out there, their trade business is often not welcomed by their fanbase, and this area remains a scope for improvement.