Sweeney has faced challenges when it comes to drafting, but his skills in making trades and securing team-friendly contract extensions have proven to be his strengths. With Sweeney recently agreeing to a multi-year contract extension, let's take a look at his top five trades during his tenure as Boston's GM.

Sending Dougie Hamilton to Calgary

In one of his early moves prior to the 2015 Entry Draft, Sweeney started reshaping the Boston team by acquiring draft picks. He traded defenseman Dougie Hamilton to the Calgary Flames in exchange for a 2015 first-round pick and two second-round picks. Although the player selected with the first-round pick, Zach Senyshyn, didn't pan out as expected, one of the second-round picks turned into a valuable player for the Bruins.

With the 37th overall pick, the Bruins selected defenseman Brandon Carlo, who has become a crucial member of the Boston defensive lineup. Carlo's imposing presence at 6-foot-6, coupled with his defensive skills and penalty-killing abilities, has made him an integral part of the team. In his seven seasons with the Bruins, Carlo has played 478 regular-season games and formed a formidable defensive pairing with Zdeno Chara.

Trade with New Jersey for Marcus Johansson

During the trade deadline, Sweeney orchestrated two trades that bolstered the Bruins' depth for a deep playoff run. In one of those moves, the Bruins traded their 2019 second-round pick and a 2020 fourth-round pick to the New Jersey Devils in exchange for forward Marcus Johansson. Although Johansson had a modest regular season with three points in 10 games, he played a significant role in the Bruins' playoff journey to the Stanley Cup Final, fueling their run to Game 7 against the St. Louis Blues.

Acquiring Charlie Coyle from Minnesota

Another crucial trade executed by Sweeney in February 2019 involved sending Ryan Donato and a fifth-round pick to the Minnesota Wild in exchange for Charlie Coyle. Coyle found his place as the Bruins' third-line center behind Patrice Bergeron and David Krejci, forming a potent line alongside Johansson and Danton Heinen. Coyle's performance in the postseason was particularly impressive, as he notched nine goals and seven assists in 24 games, solidifying his role as a key center for the Bruins. He subsequently signed a six-year, $31.5 million contract extension, further cementing his importance to the team.

Trading for Hampus Lindholm and Kodie Curran

Addressing the Bruins' needs before the trade deadline in March, Sweeney made a significant move to improve their roster for the playoffs. He sent defensemen John Moore and Urho Vaakanainen, along with three draft picks, to the Anaheim Ducks in exchange for left-shot defenseman Hampus Lindholm and forward Kodie Curran. The acquisition of Lindholm solidified the Bruins' top defensive pairing alongside Charlie McAvoy, as Sweeney wasted no time in securing Lindholm with an eight-year, $52 million contract extension. This move ensured defensive stability for the team moving forward.

Landing Taylor Hall and Curtis Lazar from Buffalo

In a crucial move at the 2021 trade deadline, Sweeney successfully acquired forward Taylor Hall and Curtis Lazar from the Buffalo Sabres. In exchange, he sent Anders Bjork and Boston's second-round pick in 2021 to Buffalo. The addition of Hall proved vital, as he injected much-needed scoring prowess and became a significant contributor on the Bruins' second line alongside David Krejci and Craig Smith. Hall's impact was evident with eight goals and 14 points in just 16 regular-season games, and the Bruins secured him for the long term with a four-year, $24 million contract. Which is a solid deal for someone of Hall's calibre, and it's moveable if they decide to go towards a rebuild near the end of his contract.