Following yet another playoff disappointment, the Toronto Maple Leafs may be shaking up not only their roster but their front office as well. Brendan Shanahan, in particular, could be heading to Long Island after the latest Game 7 loss.

Shanahan has been the president and alternate governor of the Maple Leafs since 2014, and while he earned praise at one time for building a highly skilled core of Auston Matthews, Mitch Marner, and William Nylander, he has since been criticized for that core's lack of postseason success.

Despite Toronto having made it to the postseason in eight of the past nine seasons, the NHL's most popular team is still awaiting its first conference final appearance since 2002. Additionally, the Maple Leafs have made it past the first round only twice in those eight seasons, and their season has ended in Game 7 defeats six times.

If Shanahan is ousted from his role by the Leafs, he reportedly has at least one very interested party: the New York Islanders.

“It’s not yet clear if Thursday’s board meeting will result in a final decision on Shanahan’s future,” The Athletic's Chris Johnston wrote. “In the event the organization decides to move on from him, the team will likely move forward without a team president for the foreseeable future, according to the sources.

“Further complicating the path forward with Shanahan is the fact that the New York Islanders have expressed interest in speaking to him about their top hockey job, according to league sources.”

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SportsNet's Elliotte Friedman reported Wednesday that the Islanders requested and were granted permission to speak with Shanahan about the opening in their front office.

Coincidentally, Shanahan hired Lou Lamoriello as the Maple Leafs' general manager in 2015. Lamoriello is the outgoing president and GM of the Islanders, who decided not to renew the longtime NHL executive's contract.

Unlike the Maple Leafs, the Islanders reached the Eastern Conference Finals in 2020 and the Stanley Cup semifinals in 2021. Since then, however, New York has struggled, missing the playoffs in 2022 and 2025, and being ousted in the first round in 2023 and 2024.

Lamoriello, 82, had been the president and GM of the team since 2018, when he left the Maple Leafs organization.