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

During the Toronto Maple Leafs rise to prominence in the Auston Matthews era, they had many opportunities during almost the past decade to look for ways to bolster the roster in support of the Leafs superstar and company.

The Toronto Maple Leafs had explored the trade route, making both good and not-so-good deals to address their needs in the process. In addition, they have also tried promoting some young prospects from within their organization where some showed promise and potential, whereas others ultimately flamed out in the end.

But most importantly, the Leafs made most of their major moves during free agency, with hopes that they could add solid, proven commodities that could significantly help the team get to the next level without giving up any assets.

Some of the Maple Leafs signings may have worked out in one way or another. However, there have been various others where the Leafs probably wished they had spent their money more wisely instead.

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

With the 2024 NHL free agency set to open in a little more than two weeks away, let’s take a look back at five free agent signings by the Maple Leafs since the debut of Matthews in 2016 that unfortunately didn’t produce the results that was expected of them in the end.