The Montreal Canadiens announced Sunday general manager Marc Bergevin has been fired as part of a massive front-office shakeup.
Assistant general manager Trevor Timmins and senior vice president Paul Wilson have also been relieved of their duties.
Jeff Gorton will remain with the team and serve as the executive vice president of hockey operations.
The Canadiens have been one of the worst teams in the NHL to this point, totaling only six wins and 14 points through 23 games.
The Ottawa Senators are the only team in the Atlantic Division with a worse record, but they have played four fewer games than Montreal.
The Canadiens are coming off a trip to the Stanley Cup Final last season. They narrowly made the playoffs but went on a miracle run that included wins over the Toronto Maple Leafs, Winnipeg Jets and Vegas Golden Knights before losing to the Tampa Bay Lightning.
However, Montreal now appears set to miss the playoffs for the third time in five years. Last year's run was the only time since 2015 that the squad advanced beyond the first round of the postseason.
"We wish them all the success they deserve in the pursuit of their careers," owner Geoff Molson said in a statement. "I think, however, that the time has come for a leadership change within our hockey operations department that will bring a new vision and should allow our fans and partners to continue cheering for a championship team."
Bergevin was in his 10th year as the Canadiens general manager. The 56-year-old had also spent 20 years in the NHL playing for eight different organizations, including six years with the St. Louis Blues.
The team will now begin a search for a new GM while Gorton will lead the front office in the interim. Gorton served as general manager of the New York Rangers for six seasons before he was fired in May.