Don Sweeney's biggest flaw hasn't been his trading or free agency decisions since taking over the reins as the Boston Bruins general manager. In fact, some of his decisions in that realm have stopped his tenure from being a disaster after some of the drafting that has happened under his watch. While Sweeney has been proficient with some of his decision-making, there have been a couple of signings that he'd like to have back.
Ironically, the three worst signings of his tenure show a bit of a blind spot in his and Cam Neely's decision-making. The team loves their aging two-way veterans, and while those are generally a boom-or-bust risk, the Bruins have unfortunately had a few bigger busts than they'd like to admit.
David Backes - Five-Year, $30 million contract (July 1, 2016)
If you're looking for the poster boy of taking players well past their prime (unless #3 on this list one day takes the crown), it is former St. Louis Blues captain David Backes. The power forward was one of the most exciting playoff players in the league in the early 2010s with St. Louis, culminating in his 14-point, 20-game run in his final season with the organization, but he never fully found that form in Boston.
In three seasons with the Bruins, Backes never eclipsed the 40-point mark. He appeared in three postseasons with some less-than-impressive results, including the 2019 Stanley Cup run, where he infamously became a healthy scratch in favor of Karson Kuhlman. He played 16 more games in Boston the following season, but that final playoff was the beginning of the end.
Matt Beleskey - Five-Year, $19 million contract (July 1, 2015)
Oh boy, that week in 2015 was a rough one for Sweeney. Not only did he have one of the biggest drafting gaffes in franchise history with his three picks in the first round, but he then spent $19 million on Beleskey after his breakout 2014-15 season.
Beleskey was seen as the Bruins' next great power forward a year before that moniker went to Backes, and he came well short of those expectations. He had 37 points in 80 games in his first season with the team, but played just 63 games over the next two seasons, totaling eight points.
Beleskey spent the remainder of his third year in Providence before departing the organization in a cap dump to acquire Rick Nash's contract. Beleskey would play just five more NHL games with the New York Rangers before retiring.
Elias Lindholm - Seven-Year, $54.25 million contract (July 1, 2024)
It might be a bit too early for buyer's remorse, but fans had issues with this signing the day it happened given the AAV. Some fought back that the rising cap would make this look like a steal, but Lindholm is now just a third-line center who is going to be net-negative for the Bruins if he ever has to play higher in the lineup.
To make matters worse, Sweeney's comments about his lingering back injury, saying his production drop was "just what it is," have fans dreaming about the end of this contract. Whether Lindholm finishes out his deal or ends up on long-term injured reserve because of his chronic back issue, Sweeney's decision to give him the keys to the middle of the ice to replace Patrice Bergeron is one that could end up being his worst move ever.
