The 5 Worst Toronto Maple Leafs Free Agent Signings in the Auston Matthews Era

Which players did the Leafs acquire through free agency since 2016 that didn’t end up panning out?
Jan 12, 2022; Glendale, Arizona, USA; Toronto Maple Leafs left wing Nick Ritchie (20) against the Arizona Coyotes at Gila River Arena. Mandatory Credit: Mark J. Rebilas-USA TODAY Sports
Jan 12, 2022; Glendale, Arizona, USA; Toronto Maple Leafs left wing Nick Ritchie (20) against the Arizona Coyotes at Gila River Arena. Mandatory Credit: Mark J. Rebilas-USA TODAY Sports / Mark J. Rebilas-USA TODAY Sports
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John Klingberg 

Alas, even in the Brad Treliving era as GM in Toronto, he has already registered a “miss” to his record in terms of free agent signings.

During the past offseason in 2023, Trelviing wanted to add a proven right-handed defenseman to help bolster the Leafs defensive corps’ offensive potential heading into the 2023-24 season.

As a result, the Leafs decided to ink veteran John Klingberg to a one-year, $4.15 million deal.

However, there were already red flags in his resume as his defensive play had regressed quite considerably in recent years.

Nevertheless, the Leafs believed that he could more than make up for it by being a major contributor offensively and by helping to quarterback their potent power play. Unfortunately, Klingberg would wind up being a huge disappointment for the Leafs as he struggled big time both offensively and defensively right from the start of the 2023-24 regular season.

Klingberg ended up appearing in only 14 games, with only five assists to show for while registering just two points on the power play. (All stats from hockeydb.com)

Klingberg’s season and eventual tenure with the Leafs would ultimately end when he had to undergo hip surgery in December.

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So much for one of their huge investments from the offseason. Tyler Bertuzzi and Max Domi might have ended up being solid producers in the end for the Leafs after a rough start, but the Klingberg addition certainly turned out to be a complete failure.