The Toronto Maple Leafs are heading into a crucial offseason, with significant decisions to be made regarding key players and the overall direction of the team. Several storylines are developing, ranging from contract negotiations with core players like Mitch Marner and John Tavares to celebrity endorsements and organizational changes.

One of the biggest question marks surrounding the Leafs is the future of Mitch Marner. As an unrestricted free agent this offseason, Marner's potential departure could trigger major organizational changes. While he's undeniably a superstar, the Leafs might be hesitant to open up the checkbook and offer him what he's worth, especially after another early playoff exit. Recent reports suggest that Marner could command a seven-year deal with an average annual value of $12.95 million, totaling over $90 million. Some analysts believe that Marner might prefer a quieter market away from the intense scrutiny of Toronto, with teams like Las Vegas, Los Angeles, and Anaheim being potential destinations. However, the Chicago Blackhawks, despite having ample cap space, are not expected to aggressively pursue Marner, as they are focused on long-term development through the draft. If Marner leaves, the Leafs could explore the trade market to replace him, with Dallas Stars forward Jason Robertson being a potential target.

The future of captain John Tavares is another pressing issue for the Maple Leafs. Tavares has expressed a strong desire to remain in Toronto, but with his hefty $11 million annual salary coming off the books, a significant pay cut is likely necessary. General Manager Brad Treliving has indicated that the "door is open" for Tavares' return, but both sides must compromise. One potential solution is structuring Tavares' next contract similarly to those of Yanni Gourde or Chris Tanev, with a longer term at a lower average annual value. This would provide Tavares with security while giving the Leafs more cap flexibility to improve the roster. NHL Insider Elliotte Friedman believes that if Tavares stays with the team, he could end up going the Yanni Gourde route and re-signing long-term for a discounted price.

Amidst the uncertainty and pressure, the Maple Leafs received an unexpected vote of confidence from golf superstar Rory McIlroy. McIlroy, who recently won the 2025 Masters, believes that the Leafs can end their Stanley Cup drought. "If I can win the Masters, then the Leafs can win the Stanley Cup," McIlroy said after being gifted a Leafs jersey by MLSE CEO Keith Pelley. McIlroy's support, while welcomed by some, has been met with skepticism by many Leafs fans, who are weary of unfulfilled promises. Pelley, who joined MLSE as President and CEO in April 2024, is determined to bring a Stanley Cup to Toronto. "Make no mistake about it, making the playoffs and winning rounds is not our aspirational goal; our goal is to win the Stanley Cup," Pelley stated.

The Maple Leafs are at a crossroads, and the decisions made this offseason will have a significant impact on the team's future. Whether they can re-sign Marner and Tavares at reasonable prices, find suitable replacements if necessary, and build a team that can finally contend for a Stanley Cup remains to be seen. With a new coach and key roster decisions looming, the Leafs' path forward is filled with both challenges and opportunities.