The worst free agent signing in NY islanders history

When New York Islanders fans talk about the worst free agent signings in franchise history, one name consistently rises to the top: Andrew Ladd.

Signed on July 1, 2016, to a seven-year, $38.5 million contract, Ladd was brought in by then-GM Garth Snow to help replace the departing Kyle Okposo and Frans Nielsen and provide top-six scoring, veteran leadership, and championship pedigree. The Islanders had just won a playoff series for the first time in 23 years and needed to keep momentum going despite the losses of two home grown players that were borderline All-Stars.

If you were applauding the deal, it was because Ladd was a two-time Stanley Cup champion with Chicago and Carolina and had scored 23 or more goals in five of his previous six seasons. He would be a leader in the room and would be a consistent scoring presence. But from the very start, the deal felt like a reach—and it aged poorly almost immediately.

In his first season, Ladd managed 23 goals but only 31 points, failing to mesh with John Tavares or spark the offense as hoped. From there, his play deteriorated quickly. Injuries plagued him—especially to his knees—and Ladd was eventually demoted to the AHL, sent through waivers, and exiled from the NHL roster by 2019. By the time the Isles offloaded his contract to Arizona in 2021, he had played only 181 games over five seasons, registering just 72 points—a measly return on a major investment.

Perhaps most painful for Islanders fans was not just the on-ice failure but the long-term cap implications, which handcuffed the team during key rebuilding and competitive years. Unlike other failed signings, Ladd's deal couldn't be buried easily. It lingered as a cautionary tale for the front office and fans alike.

While the Islanders have had their share of missteps in free agency, the Ladd contract stands as the worst due to its duration, cap hit, and lack of tangible impact. It represented a misjudgment in both player evaluation and timing, hindering the front office's ability to improve the roster during critical years of contention.