2. Losing out on Alex DeBrincat hurt
Lamoriello had plenty of holes to fill entering the offseason. Aside from the unrestricted free agents, the Islanders farm system is bereft of young talent. The team has not had a 1st round draft pick since Simon Holmstrom in 2019 and the closest prospect to NHL-ready, Aatu Raty, was dealt to the Vancouver Canucks for Bo Horvat. Even though the Islanders retained all of their free agents and dealt Josh Bailey to the Chicago Blackhawks, the team was still the same, meaning they had not gotten better or worse from last season.
Once all four free agents were retained and Bailey’s contract was offloaded, the Islanders were still ‘cap-strapped’ with less than $2 million to spend. When scouring the trade market for a potential salary swap, Alex DeBrincat of the Ottawa Senators made the most sense. He was a restricted free agent that did not want to sign long-term with the Senators. DeBrincat would bring an elite shot to the Isles' top line with Mathew Barzal and Horvat. At 25-years-old, nobody could blame Lamoriello for being interested.
The Islanders ended up losing out on DeBrincat as he was traded to the Detroit Red Wings for a 1st and multiple second-round draft picks. The reason behind this trade was that the Isles just did not have the draft nor the prospect capital to complete a valuable package. The hypothetical trade scenario had J.G. Pageau being sent back to the Senators, but it wasn't enough to get the Sens to bite. It’s hard to fathom how the third line would look without Pageau given the Islanders' lack of center depth, however, Pageau has struggled mightily both on the penalty kill and on offense, while DeBrincat has 17 goals and 21 assists.