The Toronto Maple Leafs, like many NHL teams, have had their share of successes and failures in free agency. While some signings have brought valuable talent and leadership to the team, others have become cautionary tales of overspending and unmet expectations. Here's a look at three of the worst free agent signings in Maple Leafs history:

1. David Clarkson (Signed in 2013)

On July 5, 2013, Leafs Nation rejoiced at the arrival of David Clarkson, a hometown kid who seemed poised to bring grit and scoring to the team. The Maple Leafs signed Clarkson to a seven-year, $36.75 million contract. Many fans were happy to have a player like Clarkson wanting to come home. Unfortunately, Clarkson's time in Toronto was disastrous.

Clarkson, who idolized Wendel Clark, faced immense pressure to perform in his hometown. His tenure got off to a terrible start when he received a 10-game suspension for leaving the bench to engage in a fight during a preseason game. He struggled to find his rhythm and never lived up to the expectations. In 118 games with the Leafs, he scored just 15 goals.

The Maple Leafs realized their mistake and traded Clarkson to the Columbus Blue Jackets for Nathan Horton less than two years into the contract. Clarkson's contract was a massive miscalculation, and the team was fortunate to find a way to offload it, even if it meant acquiring an injured player in Horton.

2. Mike Komisarek (Signed in 2009)

In 2009, then-Maple Leafs GM Brian Burke sought to add a physical presence to the team's defense. He signed Mike Komisarek to a five-year, $21.5 million contract. Komisarek had a reputation for physicality and penalty minutes during his time with the Montreal Canadiens, which appealed to Burke's vision for the team.

However, Komisarek's performance in Toronto was underwhelming. Injuries hampered his effectiveness, and his point production and physical play declined significantly. In 158 games with the Maple Leafs, he recorded just 2 goals and 17 assists.

After parts of four seasons, the Maple Leafs bought out the remainder of Komisarek's contract. Komisarek's signing failed to provide the defensive stability and toughness the team had hoped for, making it one of the worst free agent acquisitions in franchise history.

3. Jeff Finger (Signed in 2008)

Perhaps one of the most perplexing signings in Maple Leafs history was Jeff Finger's four-year, $14 million contract in 2008. Finger had played less than 100 NHL games before hitting free agency, leaving many scratching their heads at the Leafs' investment.

Then-GM Cliff Fletcher believed Finger could become a shutdown defenseman, but there's speculation that Fletcher confused Finger with another Avalanche player, Kurt Sauer. Finger's performance did not justify his contract. He played 105 games for the Leafs, recording 6 goals and 19 assists, before his NHL career ended. The Finger signing remains a baffling chapter in Maple Leafs' free agency history.