John Chayka made his first front-office hires as Toronto Maple Leafs general manager Monday morning.The new Leafs GM added Judd Brackett as an assistant general manager and former NHLer Freddie Hamilton as chief of staff.Brackett joins the Leafs after five seasons with the Minnesota Wild, where he served as the team’s director of amateur scouting. The 49-year-old previously spent 12 seasons with the Vancouver Canucks, the last five as the amateur scouting director.He will oversee player evaluation in the Leafs’ pro and amateur scouting departments.“We are thrilled to welcome Judd to our organization,” Chayka said in a statement. “He has established one of the strongest amateur scouting and drafting track records in the NHL and has consistently demonstrated an ability to adapt and evolve his approach as the game changes. As we continue to build our hockey operations department, Judd will play a key role in integrating traditional scouting, video analysis, and data-driven insights to strengthen our decision-making process.”Hamilton, in the newly created position of chief of staff, will “support strategic planning and cross-functional initiatives across the hockey operations department while working closely with the club’s leadership group.”The 34-year-old played 75 games in the NHL as a forward for the San Jose Sharks, Colorado Avalanche and Calgary Flames, as well as the Arizona Coyotes when Chayka was the GM there. According to the team, Hamilton earned his MBA from Yale University following his retirement and then worked in private equity with Bolt Ventures.Hamilton, who hails from Toronto, is the brother of New Jersey Devils defenceman Dougie Hamilton.“Since retiring, he has built an impressive career in business and finance, gaining valuable experience across investing, strategy and organizational leadership,” Chayka said of Hamilton. “His diverse background and collaborative approach will make him a valuable addition to our group as we execute key strategic initiatives and strengthen alignment across our hockey operations department.”Chayka still needs to hire a replacement for former assistant GM Brandon Pridham, the longtime front-office staff member who, among other things, managed the team’s salary cap.Shane Doan, who was hired as the special advisor to the GM under Brad Treliving, also left the organization after Chayka’s hiring as GM.Hayley Wickenheiser, Darryl Metcalf and Ryan Hardy all currently remain with the Leafs as assistant general managers.Jun 1, 2026Connections: Sports EditionSpot the pattern. Connect the termsFind the hidden link between sports terms