Top 3 Worst Free Agent Signings in Maple Leafs History

Unfortunately, Burke didn’t get what he wished for. Komisarek’s time in Toronto was awful, he scored two goals and 17 assists in 158 games. During his time with the club, he struggled with injuries which led to him becoming a worry on the backend. His PIMS were significantly lower as well, with only 169 in those 158 games, but with the injuries it made sense as to why he tried to stay out of the extracurricular activities. Thankfully for both Leafs Nation and Komisarek, his time with Maple Leafs ended after parts of four seasons when he was bought out on July 2, 2013, which was the offseason entering the final year of his deal. After the buyout, he agreed to terms with the Carolina Hurricanes on a league-minimum contract.

David Clarkson

This may be tied for the worst free agent signing in all of Maple Leafs’ history. On July 5, 2013, Leafs Nation thought the next coming of Wendel Clark had arrived. The club agreed to terms with David Clarkson, one of the biggest fish on the open market. The deal was for seven years, with an AAV of $5.25 million, for a total of $36.75 million. One of the largest contracts to be signed by the Maple Leafs in free agency, it had many fans happy to have a player like Clarkson want to come home.

Unfortunately for Clarkson, his time in his hometown of Toronto didn’t start the way he would have hoped. He was given a 10-game suspension for leaving the bench and joining a fight in a preseason game against the Buffalo Sabres. Who was that fight between? None other than Phil Kessel and John Scott, so Clarkson jumped to the defence of his teammate and was punished for it. After he served the 10-game ban, the rest of his time in the blue and white was no better and relatively short-lived. He appeared in 118 games throughout two seasons, in which he scored a total of 26 points. A very big waste of $5.25 million right? The Maple Leafs thought so too and traded him just two years into that seven-year deal to the Columbus Blue Jackets in exchange for Nathan Horton.

Horton was placed on long-term injury reserve (LTIR) and that cap space was used elsewhere. As for Clarkson, after just 26 games over two seasons, the Blue Jackets also placed him on LTIR due to a chronic injury. In 2017 his contract was traded to the Vegas Golden Knights for LTIR cap relief. A few years later in 2019, he was traded back to the Maple Leafs where he remained on LTIR until his deal expired in 2019-20.

Jeff Finger

Still to this day, members of Leafs Nation are trying to figure out why Cliff Fletcher decided to give Jeff Finger a four-year $14 million contract, even though he had played less than 100 NHL games. Yes, you read that right, he gave him a four-year contract with an AAV of $3.5 million. He spent time with the Colorado Avalanche from 2006-08 where he played in 94 games and recorded 24 points. When he hit the open market on July 1, 2008, the Maple Leafs made him an offer he couldn’t refuse.

Finger was 28 years old when he signed the deal with Toronto and was able to make the team out of camp in his first year with the club. He went on to play 66 games and score 23 points, while in his second year of that four-year deal, he appeared in only 39 games and recorded 10 points. He was placed on waivers before entering the third year of his contract and never saw an NHL game again. He spent the next two seasons with their American Hockey League (AHL) affiliate, the Toronto Marlies before being released in 2012. This was by far the biggest, if not tied with the biggest mistake in Maple Leafs’ free-agent signing history.

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Although there are still a few more that could be listed, it was best to only name what I felt were the top three worst signings in Maple Leafs’ history. Jason Blake’s contract in 2007 worth $20 million over five years and Tim Connolly’s worth $9.5 million over two seasons in 2011 were honourable mentions that could have easily made this list. However, the signings of Komisarek, Clarkson and Finger are by far the worst ever to be made; the type of contracts that NHL GMs wish they were never tied to.