When Brendan Shanahan became the Toronto Maple Leafs’ president in 2014, the city erupted with hope. For the first time in years, fans believed a winning culture might finally take root in one of hockey’s most storied but star-crossed franchises. Shanahan, a Hall of Fame player and proven winner, brought credibility—and with it, winners like Lou Lamoriello and Mike Babcock. But as time passed, that early optimism slowly faded.
Now, as Shanahan steps away from the Leafs, his time in Toronto offers a mix of progress and puzzling decisions that, ultimately, didn’t deliver the result he or the fans were chasing: a Stanley Cup.
Early Days of Hope and High Expectations
In his first few years, Shanahan’s approach looked like the perfect reset. He cleared out old habits and ushered in a modern, data-driven era. The hiring of Lou Lamoriello brought structure, while coach Mike Babcock promised discipline. The Maple Leafs drafted well, developed stars like Auston Matthews and Mitch Marner, and built a skilled, fast-paced team.
Back then, it looked like Shanahan had all the right pieces. The franchise was organized, talented, and ready to grow. But something critical was missing.
The Dubas Decision: A Turning Point
The moment that likely shifted Shanahan’s course—and perhaps doomed the vision—was when he blocked then-assistant GM Kyle Dubas from taking a job with the Colorado Avalanche. Instead, he promoted Dubas to general manager, a move that would define the next phase of the Leafs’ direction.
Dubas leaned heavily into analytics and skill, building a roster full of finesse and flash. But what it lacked was grit—the same kind of fierce competitiveness and toughness that defined Shanahan’s own playing days. Ironically, he failed to find players like himself: relentless, physical, and unshakable in the biggest moments.
Talent Alone Wasn’t Enough
Shanahan believed if you collected enough talent, hired the smartest minds, and gave them freedom, success would follow. But hockey is about more than skill. It’s also about character, urgency, and the ability to battle through tough playoff series—traits the Leafs too often lacked.
Despite making the playoffs for nine straight years, they won just two series. The team often folded under pressure, unable to handle the intensity of postseason hockey. Talent was never the issue; mental toughness was.
What Shanahan Got Right
To be fair, Shanahan didn’t leave the Leafs in chaos. He modernized the front office, brought in top-level talent, and created a consistent playoff team—something the Leafs hadn’t seen in a long time. He also helped repair the club’s relationship with alumni and the community. Toronto became a desirable destination for players again.
But in the playoffs, results are everything. And when a team repeatedly underperforms despite high expectations, someone has to take responsibility.
Looking Ahead: A Chance to Learn and Grow
Shanahan is now being linked to other teams, including a reported interest from the New York Islanders. If he takes on another front office role, it could be a fresh start. More importantly, it could be his opportunity to learn from what went wrong in Toronto.
This time, he may seek more balance—between brains and brawn, talent and toughness. If he does, Shanahan still has the chance to build a winner somewhere else.
Brendan Shanahan’s time in Toronto started with big hopes and a bold vision. He achieved many good things, from strong player development to building a professional and respected organization. But by leaning too heavily on talent and not enough on grit, his rebuild fell short of its biggest goal—a Stanley Cup. As he moves on, the next chapter may offer a shot at redemption, and perhaps, the lessons from Toronto will help him write a different ending next time.
