During his run as Bruins general manager, Don Sweeney has had his share of hits and misses at the trade deadline. But a few of those deadlines stand out above the rest, whether Boston was loading up for a playoff push or selling and retooling on the fly.
Here’s a look at the three best deadlines Sweeney has put together in Boston.
- 2025 trade deadline
Boston was still very much in the Eastern Conference playoff picture in 2025, sitting just two points out when Sweeney made the unexpected decision to sell. It was a sharp turn, but the deals that followed gave the Bruins a mix of present value and future pieces.
The Bruins got Mittelstadt, who played a major role on their second line in 2025-26, and Zellers, a prospect at North Dakota, in a move that came after Coyle left Colorado and was later traded to the Columbus Blue Jackets.
The Marchand deal is the one that stings. He went on to be a major part of the Panthers’ second straight Stanley Cup, while the first-round pick Boston received was later sent to the Utah Mammoth in the JJ Peterka trade in June of 2026.
The Carlo move was a rough one for Toronto and a useful one for Boston. Carlo struggled with the Maple Leafs before being moved in the summer of 2026 to the St.
Louis Blues. The Bruins came away with Minten, who looks like a solid building-block piece, though Boston also lost the first-round pick in 2026 after Toronto won the NHL Draft Lottery.
The trade that may linger the longest is the Jokiharju deal. Boston extended him for three years at a $3 million AAV, and that contract decision stands out for all the wrong reasons.
The Bruins did get Khusnutdinov, who has been a nice fit on the third line, while Brazeau left in free agency that summer for the Pittsburgh Penguins.
- 2019 trade deadline
This was one of the more productive deadlines of Sweeney’s tenure, and it helped push Boston all the way to Game 7 of the Stanley Cup Final at home, where the Bruins came one win short against the St. Louis Blues.
Coyle was the headliner. Boston brought him in at the deadline, and he gave the lineup real playoff stability. He produced nine goals and seven assists in 24 postseason games and became a fixture in the Bruins’ lineup for the next six years.
Johansson was another strong addition that doesn’t always get enough credit. In 22 playoff games during that 2019 run, he chipped in four goals and seven assists while logging a little more than 14 minutes per night. He was a hard-working, gritty presence during his short stay in Boston.
- 2023 trade deadline
Sweeney took his biggest swing in 2023, and it made sense. The Bruins had just set the NHL record for wins and points in a season, so going for it was the obvious play. The problem, of course, was the stunning first-round exit against Florida.
Still, the deadline itself was loaded. Hathaway came over from Washington to give Boston fourth-line grit, one of two Capitals players drawing interest around the league at the time.
Orlov, a sought-after puck-moving defenseman, also arrived from the Capitals in a separate deal and gave the Bruins another quality piece for the stretch run.
Then there was Bertuzzi, who nobody really saw coming. He fit into the top six and gave Boston another legitimate weapon up front. The playoffs ended in disappointment, but Sweeney’s approach at that deadline was easy to understand: he swung big because the Bruins were built to do exactly that.
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