Maple Leafs’ 2019 Trade Remains the Team’s Biggest Misstep of the Matthews Era

When the Toronto Maple Leafs shipped out Nazem Kadri in the summer of 2019, the move felt more like damage control than roster building. Kadri had just put himself in the spotlight for all the wrong reasons — back-to-back playoff suspensions that derailed Toronto’s chances against Boston. The organization was clearly frustrated. They needed to clean up the optics, patch holes on defense, and shuffle the lineup around Auston Matthews and John Tavares.

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But what they ended up doing was creating a void they’ve never truly replaced. This season’s results have been a glaring reminder that the Kadri trade still stands as one of the organization’s biggest mistakes. It’s undoubtedly the biggest blunder of the Auston Matthews era.

The Kadri Trade Out of Toronto

The trade — Kadri, Calle Rosen, and a 2020 third-rounder for Alex Kerfoot, Tyson Barrie, and a sixth — was supposed to check multiple boxes at once. Tyson Barrie was brought in as the puck-moving defenseman the team lacked. Kerfoot was expected to slide seamlessly into a middle-six center role. On paper, it looked tidy.

At the time, GM Kyle Dubas said, “We had a need, and from our view as a management team, we owe it to our forward group and [Frederik] Andersen in net to round it out as best we can and put the best possible team on the ice, particularly with defensemen who can move the puck effectively and efficiently to our forward group.”

On the ice? Things didn’t pan out as expected.

As Jonas Siegel of The Athletic points out, Barrie never fit Toronto’s system or the coaching staff’s expectations. He struggled defensively, never found a rhythm on special teams, and was gone after one season. Ultimately, he wound up with the Edmonton Oilers, where he was a much better fit. He was part of some big playoff runs before being used as trade material to acquire Mattias Ekholm from the Nashville Predators.

Kerfoot became a useful, adaptable two-way forward, but never the reliable full-time center Toronto needed him to be.

And Kadri? In Colorado, he became exactly the version of himself the Leafs always hoped for — a physical, relentless, 200-foot difference-maker who scored in big moments and anchored one of the best center trios in the league.

The Maple Leafs Missed Out Having 3 Top Centers

The Leafs could have rolled out Auston Matthews, John Tavares, and Kadri down the middle for years. Instead, they spent half a decade trying to patch the hole they created when they moved him.

Looking back, it’s not just that the trade didn’t work. The team dumped a superb playoff-style center from a team that still doesn’t have one. They gave away a player who later helped Colorado win a Stanley Cup and would pay almost anything years later to get him back.

The question now would be, why would Kadri, who could be traded at this year’s deadline, want to rejoin a team sitting second-last in the Eastern Conference standings?

Next: Oilers’ 2015 Trade Still Stands as the Biggest Blunder of McDavid Era