NHL-NEWS: According to ESPN, the Toronto Maple Leafs have officially announced the signing of right winger for the Philadelphia Flyers. The three-year, $27.4 million contract was reached following….

The 2024 NHL Free Agency period started earlier this month and as such I decided to take a look at the top 5 worst Toronto Maple Leafs free agent signings of all time.

The 2024 NHL Free Agency period started up this month and the Toronto Maple Leafs have already handed out over $12 million in contracts by AAV.

A couple of them are long-term contracts handed out to aging defensemen and it got me a little worried. There are always inevitably some teams that end up with egg on their face in hindsight and the Toronto Maple Leafs have set themselves up to potentially be that team.

So, as a a way to the calm nerves, I decided to take a look at a few of the worst free agent contracts signed in Leafs history.

Although I could technically go back all the way to 1917 when the franchise first started, I figured it made the most sense to set the starting point at the introduction of the salary cap.

That is when contract terms and dollar figures actually started to have a tangible effect as there is only so much money a team can allocate to players.