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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Patrick Marleau

With the new wave of talent leading the way in Matthews, Mitch Marner and William Nylander, the Leafs suddenly found themselves back in strong contending status after getting back into the playoffs during the 2016-17 season.

With everyone’s hopes and expectations suddenly raised to another level, it encouraged the Leafs to make a big splash during free agency that year to further augment the new star-studded lineup.

As a result, the Leafs decided to put most of, if not all of their marbles into the most durable NHL player of all-time in Patrick Marleau by signing him to a three-year contract with a $6.25 million AAV.

Turning already 38 by the start of the 2017-18 season, many were afraid that the contract wouldn’t age well despite Marleau being one of the most prolific scorers in the game. He had a decent first year with the Buds as he potted 27 goals and 20 assists for 47 points in 82 games played, while adding another four goals during the playoffs.

However, his game regressed considerably during his second year with the team, so much that he was deemed expendable and was eventually traded away to the Carolina Hurricanes along with a first-round draft pick for cap relief following the 2018-19 season.

The addition of Marleau wasn’t a complete failure. After all, he did bring some valuable veteran leadership to the young Leafs core and played some role in getting them into the playoffs. As a result, the signing was bad not because of Marleau’s underwhelming performance.

But with most of the young stars on team-friendly, entry-level deals, the Leafs could have spent the money better to give the team the best and strongest chance of winning the Stanley Cup. Instead, it was mostly blown on Marleau, who eventually led the Leafs to just two first round exits.

On top of that, they even had to give up a valuable asset by throwing in a first round pick to unload his albatross of a contract in the end.