Lack of Draft Capital
The Islanders have made the post-season four of the last five seasons; they are in a different position now than they were during the rebuilding period in the late 2000's, but over the last two seasons, they've had the opportunity to trade pending UFAs have decided against it.
In 2022, Zach Parise was signed to a 1-year extension while Clutterbuck, who was injured and would be shut down for the year, inked a 2-year contract to stay on Long Island. Rather than move veteran defenseman Zdeno Chara or Andy Greene, Lamoriello gave each the option to play out the season rather than be on the trade market, and both preferred to play out the season on Long Island.
While the returns would've been minimal for Chara or Greene, that would've almost certainly not been the case each of the prior two years for goaltender Semyon Varlamov. With Ilya Sorokin the team's future in net, Lamoriello twice chose not to entertain trading Varly, citing goaltending being the team's strength and the desire to retain him after the 2022-23 season as the 35-year-old hits free agency this summer.
The Islanders have shown they are more than willing to trade first-rounders for players they feel can help them in the short and long term. To Lamoriello's credit, none of the players acquired with their first-rounders over the last four years have been a rental.
However, it's not only first-round picks the Isles are without.
They don't have a third-rounder this season as the conditional pick went to Arizona to complete the Andrew Ladd deal, and next year's third-rounder has already been sent to Toronto to acquire Pierre Engvall, another UFA, at the trade deadline.
Looking ahead, the Islanders have all seven of their 2025 draft picks. We don't know if they'll be buyers or sellers at the deadline next season but with Clutterbuck, Matt Martin, and Sebastian Aho the only expected UFAs to be on the roster (Josh Bailey's future is uncertain, and a Sorokin extension is suspected to be in the cards), the result is likely to be similar to the last two deadlines.
The draft is non-exact science, and the Isles could've easily gotten the 30th pick wrong. Snow, two other times, made similar moves at the end of the first round, once taking Josh Ho-Sang and the other drafting Anthony Beauvillier. However, the organization currently doesn't have the draft capital to be aggressive on draft day. If there is a prospect they have high on their boards, their best and only option will be to wait and see if they fall.
The 2009-10 Islanders were six points out of a playoff spot when Snow traded Sutton for Ottawa's second-round pick. If he hadn't, the future and present of the organization could have been altered.
It's the type of move the current Isles won't be able to make because of their unwillingness to trade any of their pending free agents over the last two seasons.