5 major Don Sweeney mistakes that led Boston Bruins down unavoidable trade deadline path

Don Sweeney's mistakes that have led the Bruins to where they are today.
2019 NHL Awards - Nominee Media Availability
2019 NHL Awards - Nominee Media Availability | Bruce Bennett/GettyImages

Two years after setting the NHL record for wins and points in a regular season, the Boston Bruins are at a point where they needed to trade key pieces of their roster at the trade deadline on Friday. Sitting behind a handful of teams for the second Eastern Conference wild card spot, the Black and Gold are on pace to miss the Stanley Cup Playoffs.

It's not a position that the franchise and fanbase are used to, but here we are, Sweeney and the Bruins selling key players to get players and assets for the future. How did we get here? Well, there are several reasons as to why we're here, but let's not fool ourselves that Sweeney or President Cam Neely are not going anywhere anytime soon.

Over the last couple of years, several mistakes have been made by the front office that have led to the current spot they're in. Here are five major mistakes as to why Sweeney had to do what he did on Friday, because of his own doing.

Firing Bruce Cassidy

This might be at the top of the list. One month after being told he was safe, Sweeney made the drive to his suburban Boston home in early June of 2022 to fire Bruce Cassidy. It was likely done to appease the locker room and those players are not even with the organization anymore. Imagine the locker room overruling the front office?

Cassidy was quickly scooped up by the Vegas Golden Knights and led them to the Stanley Cup championship the same year that the Black and Gold set the NHL regular season records. Talk about a kick in the onions. Jim Montgomery was hired to replace him and was fired back in November, but it wasn't his fault. He didn't put together a roster that wasn't good enough to compete. Firing Cassidy is going to haunt this franchise for a long, long time.

Not re-signing Jake DeBrusk

What are the Bruins missing this season? Secondary scoring. How would Jake DeBrusk look in this lineup? Say what you will about the 14th overall pick of the 2015 Entry Draft. Yes, he was invisible some nights, but when he was playing his game, he was a major piece to the Bruins' lineup.

Boston was not willing to meet his terms money wise which led him to signing with the Vancouver Canucks in free agency last summer and the Bruins have never rebounded from that. He was key on the power play, he killed penalties and got to the dirty areas of the ice near the net. Boston missing him this season is a major understatement.

Free agent signing's of Elias Lindholm and Nikita Zadorov

Sure, it's only been a year, but what a major swing and a miss this is looking like so far. All we heard about was Sweeney's large amount of cap space in the summer of 2024 and these two were the biggest signings, and they are turning into the biggest disappointments in 2024-25.

Lindholm was injured in camp and maybe he's still injured. He better hope that's the reason for his season to date. If not, this is going to rank up there as one of the worst contracts Sweeney has dished out. Zadorov has been a bust on the backend. From visiting the penalty box on what seems like a nightly basis to his unlucky play in the defensive zone. If both players come back next season and are the same players, then Boston has bigger problems than we think they have now.

Not replacing Patrice Bergeron or David Krejci

When the Bruins were eliminated from the first round of the Stanley Cup Playoffs in 2023 in the opening round against the Florida Panthers, who rallied from a 3-1 series deficit, you got the feeling that it was the end of the Patrice Bergeron and David Krejci era in Boston. That became reality over the summer when both announced their retirements.

Sweeney has yet to fill the void left up the middle by his two franchise centers. Pavel Zacha and Charlie Coyle were the replacements and did a good job filling those spots, but they were not the long-term answers. Lindholm is not the long-term answer and now there is no long-term answer in the organization. Shame on Sweeney for not having a plan when the day finally came that neither player was going to be around anymore. Front office malpractice at its best.

Trading Linus Ullmark & getting an underwhelming return

Ok, so yes, Sweeney needed to trade Ullmark, but with the return he got, it may have been just best to hold onto him. Honestly, sending him to the Ottawa Senators for Mark Kastelic, Joonas Korpisalo and a first-round draft pick was underwhelming. Kastelic has been a decent fourth-line addition and Korpisalo has been good this season, but why break up the strength of your team for that return?

To add insult to injury, Jeremy Swayman sat out all of training camp without a contract, and if that was even going to be a question as to whether or not that was going to happen, you don't deal Ullmark. You keep him, see how things play out, and then trade him. The return couldn't have been worse than. what it was at the time.

There is no easy and quick fix and this off-season is going to be the biggest for Sweeney in terms of upsetting the remaining core. Easier said than done.