Don Sweeney has done more right than wrong on the trade front since taking over as general manager of the Bruins, but a few deals still stand out for all the wrong reasons when you look back at them now.
One of the ugliest examples came in the David Backes mess. The first misstep was obvious enough: Boston handed Backes the huge contract in the first place.
Then came the attempt to clean it up, sending him to the Anaheim Ducks in a deal that also cost the Bruins Axel Andersson and a first-round pick in order to land Ondrej Kase. In hindsight, that package looks brutal.
Kase’s run in Boston and the NHL was cut short by a string of head injuries, and he managed only 20 games total over two seasons in Boston. The first-rounder included to push the deal through became Jackson LaCombe, a player who would have fit nicely on the Bruins’ blue line.
The Rick Nash deadline deal also looked far better in the moment than it does now. Nash arrived at the 2018 deadline and gave Boston a little burst, but not enough to justify what the Bruins paid.
He finished with six regular-season points and added five more in the playoffs, before Boston fell to the Tampa Bay Lightning in five games in the first round. The Bruins did move on from Ryan Spooner and Matt Beleskey, and that part of the deal wasn’t painful.
What hurt was the rest of the package: Ryan Lindgren and a first-round pick that turned into K’Andre Miller, both of whom became major pieces for the New York Rangers in the early 2020s and beyond, including Miller’s first Stanley Cup with the Carolina Hurricanes.
Then there’s the Dougie Hamilton trade, which was supposed to help Boston reset and stock up on future assets. The Bruins dealt Hamilton and Milan Lucic before the 2015 draft as part of a mini-retool that was meant to clear cap space and set up what came next.
On paper, it made sense. In practice, it didn’t really solve anything, because the draft return never delivered.
The relationship with Hamilton may have been beyond repair by then, but the Bruins still would have benefited far more from a right-shot defenseman like him in the late 2010s than they ever got from Jakub Zboril or Zach Senyshyn.
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Yemelyanov has handled center responsibility well enough to keep pushing his case for a larger role, and his development has already turned some heads inside a system that tends to reward patience. After a strong 2025-26 stretch in the MHL, his trajectory now points toward a full KHL season sooner rather than later, which is the sort of progress Boston always wants to see from a pick that came with upside rather than certainty. [Read more 🡒]