On , following Lou Lamoriello's retirement from management, Roy was promoted to general manager. Under Roy, the team went , making the playoffs. Desrosiers, the assistant coach, was promoted to head coach the same day.
On , Lamoriello announced his retirement as GM. Lamoriello served as general manager since the 2018–19 season with the team making the playoffs four times and advancing to the conference finals in both 2020 and 2021. Roy, the head coach, was subsequently promoted to GM the same day.
On , Sullivan was fired after eight-and-a-half seasons. Under Sullivan, the team went , making the playoffs his first six seasons and winning the Stanley Cup in both 2016 and 2017.