GM Chayka continues Maple Leafs remake with two front-office hires

New Toronto Maple Leafs General Manager John Chayka, left to right, MLSE President and CEO Keith Pelley, and new Toronto Maple Leafs Senior Executive Advisor, Hockey Operations, Mats Sundin, hold a press conference in Toronto on Monday, May 4, 2026. THE CANADIAN PRESS/Arlyn McAdorey

The Toronto Maple Leafs continued to reshape their front office Monday, hiring Judd Brackett as assistant general manager and Freddie Hamilton as chief of staff.

Brackett, who spent the last five seasons as the Minnesota Wild’s director of amateur scouting after 12 years with the Vancouver Canucks organization, will oversee amateur and professional player evaluation for Toronto.

Hamilton, a former NHL forward, joins after earning an MBA from Yale University and working in private equity.

The hires are the latest moves under new general manager John Chayka, who was brought in last month alongside senior executive adviser Mats Sundin as part of an organizational overhaul. Toronto also fired head coach Craig Berube last month after a disappointing 2025-26 season.

Chayka said Brackett’s scouting background and Hamilton’s business experience will strengthen the club’s hockey operations department.

The Maple Leafs hold the first overall pick in this month’s NHL draft after winning the draft lottery.

This report by The Canadian Press was first published June 1, 2026.