freddie hamilton is now the Toronto Maple Leafs’ Chief of Staff in their hockey operations department, a move that adds a former NHL player with business and finance experience to the club’s planning group. The appointment puts him alongside the leadership team as the Maple Leafs expand the roles around player evaluation and decision-making.
The Maple Leafs also announced Judd Brackett as Assistant General Manager, Player Evaluation. Hamilton, 34, will support strategic planning and cross-functional initiatives across hockey operations while working closely with the club’s leadership group.
Hamilton’s path to Toronto
Hamilton reached the NHL after the San Jose Sharks selected him in the fifth round with the 129th overall pick in the 2010 NHL Draft. He went on to play 75 NHL regular-season games with San Jose, Colorado, Calgary, and Arizona before retiring.
That playing résumé is only part of what Toronto is buying. After retirement, Hamilton earned his MBA from Yale University and gained experience in private equity with Bolt Ventures, giving him a background that reaches beyond the rink and into the business side of operations.
Brackett joins player evaluation
Brackett’s hire runs in parallel with Hamilton’s and gives the Maple Leafs another experienced voice on the scouting side. He will oversee player evaluation across both amateur and professional scouting after five seasons with the Minnesota Wild as Director of Amateur Scouting and 12 seasons with the Vancouver Canucks before that.
He also worked with Team USA at each of the last three IIHF World Junior Championships, a sign of how much of Toronto’s front-office reset is being built around evaluators with long records in scouting and development. John Chayka said the club is thrilled to welcome Brackett and said Hamilton stood out through his character, professionalism, and work ethic during his playing career.
Maple Leafs widen hockey operations
Chayka also said Hamilton’s background in business and finance, including investing, strategy and organizational leadership, made him a fit for the department’s next stage. In practical terms, the Maple Leafs are adding a chief of staff who will help connect planning, scouting and internal alignment while Brackett takes on player evaluation across two levels of scouting.
For Toronto, the change is not about one name alone. It is about a front office adding two different skill sets at once, with Hamilton’s cross-functional role and Brackett’s scouting background both feeding the same hockey operations structure.
