During his time as general manager of the Boston Bruins, Don Sweeney has made some trades that have worked out really well and some that haven't. However, there are three trade deadlines that stick out for a couple of reasons.
There were some deadlines where the Black and Gold were buyers for a deep Stanley Cup Playoff run, while there were some where they were selling pieces and tooling on the fly. I know that is self-explanatory. With all of that said, here are the three best trade deadlines for Sweeney as general manager.
Ranking Don Sweeney's 3 best trade deadlines
3. 2025 trade deadline
As the 2025 trade deadline approached, the Bruins were in the thick of the Eastern Conference playoff race, just two points out, when Sweeney decided to make a bold move and become a seller. It was surprising, but here are the deals he pulled off.
This has the potential to be a good deal for the Bruins. Coyle left Colorado after a couple of months when he was traded to the Columbus Blue Jackets. The Bruins have Mittlestadt, who played a big part of their second line in 2025-26, while Zellers is a promising prospect at North Dakota.
This one hurts as Marchand went on to play a big role in the Panthers winning their second straight Stanley Cup, while the first-round pick Sweeney received was moved to the Utah Mammoth as part of the JJ Peterka trade in June of 2026.
What a fleecing this was. To nobody's surprise, Carlo struggled in Toronto, and it didn't take long for Leafs fans to want to run him out. He was traded in the summer of 2026 to the St. Louis Blues. Boston has a nice building-block piece in Minten, but it did lose the first-round pick in 2026 after the Maple Leafs won the NHL Draft Lottery.
The trade that will haunt for years. Why Sweeney extended Jokiharju for three years at a $3 million AAV is a head-scratcher.
Boston acquired Khusnutdinov, who has been a nice piece on the third line, while Brazeau left in free agency that summer for the Pittsburgh Penguins.
2. 2019 trade deadline
This deadline was a productive one that saw the Black and Gold come one win away in Game 7 of the Stanley Cup Final at home from winning a Cup against the St. Louis Blues.
Picking up Coyle at the 2019 deadline was a big move as he solidified the lineup for the playoffs. In 24 postseason games, Coyle had nine goals and seven assists. What a deal this was, as Coyle was a staple in the Boston lineup for the next six years.
A very underrated deal, Johansson had four goals and seven assists in 22 playoff games in the 2019 run, while averaging just over 14 minutes a game. He was a gritty, but again, underrated forward during his short stint in Boston.
1. 2023 trade deadline
You can't blame Sweeney for swinging big at the deadline for a team that set the NHL record for wins and points in a season. However, a stunning first-round elimination at the hands of Florida will hurt for a long time.
Hathaway was one of two Capitals players whose teams were coveting at the deadline, and Sweeney landed him for fourth-line grit.
A very good puck-moving defenseman, Orlov was also a coveted player by teams, and in a separate deal with the Capitals, Sweeney landed him as well.
In a move that nobody saw coming, the Bruins struck gold with Bertuzzi, who solidified the top six. However, the swing-and-miss in the playoffs hurts, but you can't blame him for swinging as big as he did.
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