How's this for an offseason nightmare? Ullmark stays and Swayman signs an offer sheet

The Boston Bruins have money. General manager Don Sweeney projects to spend most, if not all, of the approximately $20 million that will become available on July 1. 

Being liberal with his checkbook, however, does not necessarily guarantee Sweeney success in reinforcing his roster. If certain circumstances fail to align, the Bruins could fall short in taking advantage of their spending power.

Here are seven ways things could go sideways this summer:

1. A Linus Ullmark trade doesn’t happen. Ullmark currently has 16 teams on his no-trade list, per CapFriendly. It goes to 15 teams on July 1. While there may be wiggle room in terms of clubs Ullmark would be willing to consider, there are still a significant number of market-reducing roadblocks that could limit the Bruins’ return.

Sweeney is not one to come off his price, whatever that may be for the 2023 Vezina Trophy winner. So if Ullmark’s list influences his market, the Bruins may not have a choice but to bring him back for the fourth and final season of his $20 million contract.

This would leave the Bruins without the futures — they do not pick until Round 4 of the draft this month — they want to add. It would keep Ullmark’s $5 million average annual value occupying critical cap space that could be applied elsewhere. It would put Brandon Bussi, the No. 3 goalie, at risk of being claimed on waivers.

2. Jeremy Swayman signs an offer sheet. The Bruins would match because of their cap space and Swayman’s long-term importance. But it would be a cap-crunching mechanism for the Ottawa Senators, for example, to whittle away at their Atlantic Division opponent’s advantage. Depending on the value of the offer sheet, it may limit the Bruins from signing a top-six forward, for example.

The threat of an offer sheet is one reason the Bruins have to be within a reasonable range of Swayman’s ask.

3. Swayman files for arbitration again. Last year, a hearing produced a one-year, $3.475 million agreement. But it came at a cost. Swayman did not enjoy the process. Arbitration is not fun for either side as they argue their respective price points.

Both Swayman and the Bruins want a long-term deal. But if the separation between the parties’ cases is too wide to settle via organic negotiations, Swayman may believe arbitration would work out in his favor. If he got through one hearing, he may think enduring a second one would be worth the discomfort.

4. Jake DeBrusk signs elsewhere. It appears likely that this will be the case. The Bruins will not be better off for it. The 27-year-old is an important top-six wing who raises his hand for every situation. 

5. The Bruins come up empty at the higher end of free agency. Sweeney noted the need to improve the team’s secondary offense. By that principle, the GM would stay out of the bidding for Sam Reinhart, Jake Guentzel and Steven Stamkos, the top three pending unrestricted free agents. The wisdom of that approach remains to be seen. 

As for the second tier, the Bruins would welcome forwards such as Elias Lindholm, Jonathan Marchessault and Matt Duchene. But if the prices aren’t right, Sweeney is not wired to overspend. 

The Bruins need line-drivers more than value adds.

6. The Bruins do not progress on a Brad Marchand extension. Sweeney has said Marchand deserves to be a lifelong Bruin. But if the Bruins disagree with Marchand’s expectations for his next contract, they will risk their captain entering his walk year without peace of mind.

The Bruins would still have months to work on a deal during the season. But it might leave Marchand unsettled.

Bruins captain Brad Marchand has one year remaining on his contract. (Maddie Meyer / Getty Images)

7. Matt Poitras, Fabian Lysell and Georgii Merkulov stall in their development. The three forwards have the skill to make the 2024-25 roster. Poitras, in particular, is expected to be a go-to contributor. 

But part of their offseason mandate is to become sturdier for NHL battle. If they don’t progress to becoming stronger on pucks and more competitive in 50-50 engagement, the coaching staff will not trust them in critical situations. The Bruins need internal contributions to supplement their expected offseason additions.

Coming on Thursday, a dream offseason.

(Top photo of Jeremy Swayman: Christian Petersen / Getty Images)