How the Kyle Dubas vs. Lou Lamoriello Decision Shaped the Maple Leafs – The Hockey Writers – Toronto Maple Leafs

It’s one of the biggest “what ifs” in recent Toronto Maple Leafs history: what if Lou Lamoriello had remained as general manager (GM) instead of Brendan Shanahan handing the job to Kyle Dubas in 2018? The decision marked a turning point in the franchise’s trajectory.

Related: Ex-Maple Leafs’ GM Dubas: Symbol of Hockey’s Generation Gap

Now, looking back, it’s fair to ask whether things might have turned out differently had the three-time Stanley Cup winner stayed in charge.

Lamoriello Was Shanahan’s Mentor, Then He Was Replaced

When Lou Lamoriello arrived in Toronto in 2015, the understanding was that he’d serve as a short-term mentor to Brendan Shanahan, who was still learning the ropes as team president. Lamoriello was already one of the most respected executives in NHL history — a no-nonsense leader who had built championship rosters with the New Jersey Devils.

But after three seasons, Shanahan decided it was time for a change. Lamoriello, still energetic and not ready to retire, was replaced by his much younger assistant, Kyle Dubas.

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Dubas, then just 32 years old, was seen as a progressive, forward-thinking “yes-man” to Shanahan’s vision. He brought youth, smarts, and optimism to his new job. He also surrounded himself with solid young thinkers who brought a modern analytics approach. That said, did his inexperience in managing a star-studded roster come back to haunt him and the Maple Leafs?

Would Lamoriello Have Handled the Core Four Differently?

One of the stark contrasts between the two GMs lies in contract negotiations. Under Dubas, the Maple Leafs’ young stars — William Nylander, Auston Matthews, and Mitch Marner — each signed big-money extensions with heavy signing bonuses, no-movement clauses, and top-of-the-market salaries. Critics argue the players and their agents “walked all over” the front office.

Although looking back, one can find anomalies, Lamoriello had a reputation for being unflinching at the negotiating table. It’s hard to imagine him giving up term, cap space, and trade flexibility so freely. He might have played hardball, delaying extensions or pushing for more team-friendly deals. At the very least, it’s doubtful all three contracts would have been so…