Auston Matthews signed his extension in February 2019. William Nylander signed his that December before that. Mitch Marner followed in September 2019.
All three deals landed within a tight two year window, right before the whole league's finances changed overnight.
COVID hit in 2020, and the salary cap basically froze. It crawled from $81,500,000 to just $83,500,000 between 2020 and 2024.
That's four years of almost nothing, right as Toronto was locked into three max-value stars signed under the old assumption that money keeps flowing in.
Those contracts were built on a simple bet. The cap had spiked before, after Vegas joined the league, and everyone expected it to keep climbing the same way.
Instead, the pandemic wiped out the arena revenue, the Seattle expansion cash, all of it, right as Toronto's biggest bills came due.
This isn't about letting Kyle Dubas, Lou Lamoriello, or Brad Treliving off the hook for how this roster got built.
Celebrini's timing looks nothing like Toronto's core
But it's fair to wonder how different those years look if the cap keeps rising the way it was supposed to.
Zach Hyman became the clearest cap casualty of that stretch, moved on from Toronto because there simply wasn't room to keep him.
Matthews now carries a $13,250,000 cap hit, and Nylander sits at $11,500,000, numbers locked in during a period when Toronto had almost no flexibility to work around them.
Compare that to where things stand today. The cap sits around $104,000,000 right now, and it's projected to climb to $113,000,000 within a year.
That's real room, the kind Toronto never had while trying to build around its stars in the early 2020s.
Would those three Toronto extensions have looked completely different if they'd waited two more years to sign?
Almost certainly. If that money simply wasn't available yet, those AAVs likely come in lower, and Toronto keeps more flexibility around its core.
Timing turned three max value extensions into a half decade of roster strain, and that's a different story than pure asset mismanagement.
Nobody's excusing how those years played out in Toronto. But the cap freeze that followed those signings deserves just as much blame as any front office decision that came after it.
Was COVID's cap freeze the real reason the Maple Leafs struggled to build around their stars?
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