Don Sweeney's weak spot as a general manager isn't actually trading, as he has more wins than losses in that area since taking over the Boston Bruins. However, there are still some moves that slipped through the cracks and don't look half as good in hindsight. Let's take a look at three of the worst ones.
David Backes Contract Dump
The first mistake for Sweeney in the David Backes ordeal was signing him to the massive contract to begin with, but then he tried to make it right by forcing a trade to the Anaheim Ducks. The Bruins included Axel Andersson and a first-round pick in the trade for Ondrej Kase to get the deal done, and it ended up being a disaster with the benefit of hindsight.
Kase's Bruins and NHL career was a tragic one, playing just 20 games total in two seasons in Bosont after a ton of head injuries. The first-round pick that Sweeney included to get Anaheim to take Backes ended up being Jackson LaCombe, who would've been a great addition to the Bruins' blueline if Sweeney had taken him.
Rick Nash Trade Deadline Rental
Rick Nash was a cool deadline acquisition at the 2018 deadline, but it was another addition for the Bruins that came a little too late in the respective player's career. Sweeney gave up a haul for six regular season points and an additional five points in the playoffs, which ended in a five-game defeat to the Tampa Bay Lightning in the first round.
The trade included two roster players in Ryan Spooner and Matt Beleskey, which wasn't a substantial loss by any means, but the inclusion of Ryan Lindgren and a first-round pick that ended up being K'Andre Miller was tough after seeing the value of those players for the New York Rangers in the early 2020s and still today after Miller's first Stanley Cup with the Carolina Hurricanes.
Dougie Hamilton Trade Achieved Nothing
The Bruins went through a mini-retool that somehow worked when they traded Dougie Hamilton and Milan Lucic before the 2015 draft to accrue some draft picks. It made sense after a great five-year stretch that Boston needed to shed some cap space and build towards the future, but the Hamilton trade didn't actually accomplish anything because of Sweeney's drafting mistakes.
The Bruins-Hamilton relationship may have been past repair with all the nonsense that surrounded it during that time, but the right-shot defender sure would've helped Boston through the late 2010s more than Jakub Zboril or Zach Senyshyn ever did.
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