Top 5 Worst Toronto Maple Leafs Free Agent Signings of All Time

1. David Clarkson

Seven year $5.25M AAV 8.1%

Though this contract was somehow easy to get out from under, thanks to Nathan Horton having a major back injury that would force him to stay on LTIR for the rest of his career; There is no sugarcoating that the Clarkson deal was the worst in team history and one of the worst in league history. 

After he signed in the summer of 2013, he was put on the cover of The Hockey News with the infamous photo shopped cut that bled blue.

He drew comparisons to fan favourite Wendel Clark, with many giving him the moniker “Wendel Clarkson”. To say that the media and fanbase overhyped him would be the understatement of the century.  Even for critics of the signing, no one could have predicted just how badly his tenure would play out. Despite consistently hovering around 10-15 goals and 20-25 points, people seemed to cling onto his outlier 30 goal and 46 point season two years prior. 

Before he was even able to play an actual regular season game, he was slapped with an automatic ten-game suspension for leaving the bench to join a fight against enforcer John Scott. Then, when he actually did play… It wasn’t pretty. In 60 games in 2013-14, Clarkson scored a total of five goals and 11 points but was able to serve and protect his goaltender's water bottles like no other.

In 2014-15, in Dave Nonis’ parting gift to the Leafs, after Clarkson played 58 games scoring an improved 10 goals and 15 points, he undid his wrong and sent him to the Columbus Blue Jackets for Nathan Horton’s contract. 

The Clarkson tenure in Toronto was thankfully quick but it was definitely not painless. He was ultimately miscast and with many players on this list, it is not on them at all. In almost every case when a bad contract is signed, the onus is on the team. Just about every player gives it their all and tries their hardest to play at their best. 

On a positive note, the most recent contract on this list was signed seven years ago. Thankfully, current GM Brad Treliving has no history of signing albatross contracts so this list is not at risk of going out of date anytime soon… Right?