Latest Update: The Boston Bruins’ highly regarded left winger, Brad Marchand, has canceled his contract following a heated argument with…

The struggle intensifies on Monday for the Boston Bruins and Jeremy Swayman in their restricted free agency deadlock.

The pressure is mounting on the Boston Bruins and their No. 1 goaltender, Jeremy Swayman, in their standoff over his restricted free agency, especially with a key deadline approaching on Monday.

By 5 p.m. Monday, all 32 teams must submit their season-opening rosters, marking the beginning of 192 days of salary cap calculations for the 2024-25 regular season. If Swayman remains unsigned at the start of the season, the cap hit for the first year of his new contract will be higher for the Bruins than in the subsequent years, creating potential complications for their cap management.

Conversely, each day Swayman is without a contract means he won’t be getting paid. If he signs for $8 million annually, his salary would be prorated based on the number of days left in the season. Although the Bruins could compensate for this lost income with an upfront signing bonus, it would further inflate the cap hit.

Each day without a deal affects both Swayman’s finances and the Bruins’ salary cap. This situation suggests that Swayman should receive Boston’s best offer either Sunday or Monday morning, if he hasn’t already.

Sources have confirmed that the Bruins have offered a $64 million contract, though it’s unclear if this was presented before or after Cam Neely’s recent comments.

Swayman’s agent, Lewis Gross, has experience in such negotiations. His client, William Nylander, went to the deadline with the Toronto Maple Leafs in 2018, ultimately signing a $45 million, six-year deal. Although this typically would carry a $7.5 million cap hit, Nylander’s first-year cap hit was $10.27 million due to the structuring of the deal. This arrangement worked for the Maple Leafs at that time, as they had more cap flexibility.

However, the Bruins face significant challenges in how they can structure Swayman’s contract, given their limited cap space as this negotiation continues. Additionally, there appears to be a tighter timeframe for Swayman to receive a signing bonus, as this would only increase the overall cap hit.