The Maple Leafs are now faced with critical decisions as they look to the future. With the team's first overall pick in the 2026 NHL Draft Lottery, general manager John Chayka must decide whether to draft a dynamic playmaker or trade out of the pick in hopes of acquiring a true superstar. The future of Auston Matthews, who has two years left on his deal at $13.25 million per season, also weighs heavily on these decisions.

Chayka could let input from Matthews guide his search for a new coach, but can he guarantee the captain will still be on the roster in three years? Regardless of how Chayka arrives at his decision, the next coach must be able to get more out of the Maple Leafs offensively.