The Toronto Maple Leafs are facing significant challenges as the new season approaches, with two key player-related issues. Defenseman Jani Hakanpaa’s signing has stalled due to serious knee injury concerns, leaving his future with the team uncertain. Meanwhile, left winger Nick Robertson has requested a trade and remains unsigned, with ongoing negotiations at a standstill. Despite the team’s need for Robertson, who showed promise last season, the lack of depth at left wing and his desire to leave complicate the situation. General Manager Brad Treliving acknowledges the importance of both players but solutions seem elusive as training camp nears.