As the rest of the league focuses on their newest acquisitions, the Islanders have a different agenda. Their attention lies with their longest-serving player. With no first-round pick and the NHL’s first buyout period ending soon, general manager Lou Lamoriello’s priority during the first round is to explore trade opportunities to offload Josh Bailey and free up his $5 million contract. Lamoriello has expressed his commitment to sticking with the current group of players that secured a playoff spot on the final day of the season, only to be eliminated in the first round by the Hurricanes. To move forward and make any other moves, Bailey’s departure is necessary. Despite being the longest-tenured player for any New York team, both Bailey and Lamoriello have acknowledged that his time with the Islanders is coming to an end. After a lackluster regular season, Bailey was benched for all six playoff games. He stated on the breakup day that he does not want to spend his time sitting in the stands. The question is not whether Bailey will be on the roster next season, but rather how the Islanders will handle his departure. The ideal scenario would involve a trade without retaining any salary, considering the Islanders will have limited cap space available when free agency begins on July 1. The team intends to re-sign four unrestricted free agents and one restricted free agent, which makes maneuvering financially challenging with Bailey’s contract still counting against the cap. The available landing spots for Bailey are limited, with Anaheim and Chicago being the standout options. The Islanders would likely need to add incentives to sweeten any deal, which adds another layer of complexity. Additionally, the Islanders lack trading assets due to the absence of first and third-round picks in this year’s draft, as well as a third-round pick in next year’s draft. While having five picks in this draft is beneficial, clearing cap space takes precedence. If a trade doesn’t materialize, the Islanders may opt to buy out Bailey on Friday. This would save them $2.33 million in cap dollars for the current season but result in a $1.16 million hit in 2024-25, when the flat cap era is expected to end. Lamoriello is known for his secrecy, so there might be unexpected moves. However, given his faith in the current team and the limitations in cap space and draft picks, it seems unlikely that any significant moves are on the horizon. Nevertheless, one’s failure of imagination could be the underestimation of Lamoriello’s ability to surprise.
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