Don Sweeney has had enough hits in Boston to keep his tenure from turning into a disaster, but the misses on his ledger are hard to ignore. And when you line up the worst contracts of his Bruins run, a clear theme jumps out: the organization’s comfort with aging two-way veterans has come back to bite it more than once.
The most painful example is David Backes, who signed a five-year, $30 million deal on July 1, 2016. Backes arrived with the reputation of a heavy playoff performer from St.
Louis, where he had been one of the league’s most compelling postseason players in the early 2010s. His final season with the Blues ended with 14 points in 20 games, but that version of Backes never really showed up in Boston.
Over three seasons with the Bruins, he never got past 40 points, and his playoff run in 2019 became especially memorable for the wrong reasons when he was made a healthy scratch in favor of Karson Kuhlman. He played 16 more games the next season, but that 2019 playoff run felt like the start of the end.
Matt Beleskey was another expensive swing that never paid off. On July 1, 2015, Sweeney handed him a five-year, $19 million contract after Beleskey’s breakout 2014-15 season.
For a brief moment, he looked like Boston’s next big power forward. Instead, the production fell off fast.
He put up 37 points in 80 games in his first year with the Bruins, then managed only eight points across 63 games over the next two seasons. By the third year, he was spending the rest of the season in Providence before the Bruins moved on from him in a cap dump tied to Rick Nash’s contract.
Beleskey would go on to play just five more NHL games with the New York Rangers before retiring.
The newest name on the list is Elias Lindholm, and it may be too early for full buyer’s remorse, but the warning signs are already loud. Boston signed him to a seven-year, $54.25 million contract on July 1, 2024, and the reaction from fans was skeptical from the start because of the average annual value.
Some argued the rising cap would soften the blow, but Lindholm is now viewed as a third-line center who would be a net-negative if forced higher in the lineup. His production drop has only intensified the frustration, with the Bruins’ own response being described as “just what it is,” and that has fans looking ahead to the end of the deal.
If he finishes the contract or ends up on long-term injured reserve because of his chronic back issue, the decision to hand him the middle of the ice after Patrice Bergeron could stand as Sweeney’s worst move yet.
In Other News...
Bruins Get An Early Warning Sign About Where This Team Is Headed
An early look at the 2027 NHL draft landscape is not exactly flattering for Boston, and it hints at where the Bruins may be headed if the current trajectory holds. The projection suggests a season in which they land outside the playoff field and wind up in the bottom third of the league, a sharp reminder that the gap between staying competitive and sliding backward can close fast in this sport.
There is at least a little draft-side intrigue mixed into the concern, because Boston is also slated to add another first-rounder in the deal with Toronto. Even so, the larger takeaway is the one Bruins fans would rather avoid: the Maple Leafs are being forecast as the stronger playoff bet, while Boston is staring at a much rougher path and the kind of reset that can show up in the standings long before it shows up in the draft room. [Read more 🡒]
Bruins Fans Have Real Reason To Watch Connor Hellebuyck Now
Connor Hellebuycks trade situation has suddenly become one of the more intriguing storylines in the NHL, and Bruins fans have a legitimate reason to keep an eye on it. The Winnipeg Jets goalie has been part of the leagues upper tier for a while now, and his recent play, along with his Olympic success, only adds to the appeal for any team looking for a proven answer in net.
Boston is among the clubs that will be watching closely as the market starts to take shape, because a goalie of Hellebuycks caliber can alter the balance in a hurry. The bigger question now is where the bidding goes from here, and whether the Bruins end up with a real path to get involved while other interested teams begin to circle. [Read more 🡒]
Bruins Sixth-Round Pick Is Forcing A Faster Rise Than Expected
Kirill Yemelyanov was supposed to be the kind of later-round Bruins pick who could take his time climbing the ladder, but his early run in Russia has made that path look a little shorter than expected. The 2025 sixth-rounder has already been noticeable in the MHL and has carried that momentum into early KHL preseason work with Lokomotiv Yaroslavl, where his usage alone says plenty about how quickly he is earning trust.
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 🡒]