5 worst contracts signed in Toronto Maple Leafs history feat. Dion Phaneuf’s $49 million deal 

By Nestor Quixtan

Modified Jul 19, 2024 04:14 GMT

The Toronto Maple Leafs have one of the worst track records in the NHL when it comes to contracts, often overpaying for declining players. That trend has led to some of the worst contracts in league history. The players on this list were big bets but ultimately came up short during their time in Toronto.

Here’s a closer look at the five worst contracts signed in Toronto Maple Leafs history.

5 worst contracts signed in Toronto Maple Leafs history

#5: Jeff Finger

In 2008, then-GM Cliff Fletcher bet big on Jeff Finger, a young player who had less than 100 games of NHL experience. Perhaps Fletcher saw something that made him believe Finger was worth a four-year, $14 million deal.

The deal was huge at the time but it did not pay off. He played a total of 99 games, producing 25 points and notching a minus-18 rating. He was gone by the second year of the contract.

#4: Mike Komisarek

Komisarek was another big bet on a defenseman that didn’t pan out. This time, Brian Burke sought Komisarek since the bulky defenseman fit Burke’s vision of tough, “truculent” players. After several unimpressive seasons in Montreal, Burke signed Komisarek to a five-year $22.5 million deal.

The deal was a head-scratcher since the most Komisarek had produced was 19 points in 82 games. While a reliable defenseman, Komisarek was not considered worthy of such a deal.

Ultimately, Komisarek had only one decent season in Toronto, scoring 10 points in 75 games. He finished out the contract in Carolina where he registered four assists in 32 points to go with a minue-4 rating.

#3: Patrick Marleau

Marleau was a San Jose Sharks legend when he decided to test free agency in 2017. Then-GM Lou Lamoriello felt Marleau would be a great influence on young stars Auston Matthews, William Nylander and Mitch Marner.

Lamoriello was right. Marleau acted like a big brother on the up-and-coming Toronto Maple Leafs team. However, Marleau’s deal became a heavy burden when he signed a three-year, $18.75 million deal. The $6.25 million cap hit further hamstrung the Leafs as Marner, Nylander and Matthews needed new contacts.

So, Marleau became a cap dump, subsequently sent to the Carolina Hurricanes. The Canes put Marleau on waivers allowing him to return to San Jose to finish off his career.

#2: David Clarkson

Clarkson is arguably one of the worst blunders in NHL history. Clarkson had come off a 24-point season with the New Jersey Devils in 2012-13. However, the Leafs management felt that Clarkson was worth a seven-year, $36.7 million deal.

Toronto was banking that Clarkson could become the 30-goal scorer he had been the year before. If so, he would have become the perfect combination of skill and toughness.

However, that was not the case. Clarkson notched just 11 points in 60 games during his first season and 15 points in 58 games the following season. Clarkson was soon shipped off to the Columbus Blue Jackets for Nathan Horton’s contract.

The Blue Jackets placed Clarkson on LTIR after 24 games over two seasons. Clarkson’s contract got traded multiple times to teams looking to get around the salary cap.

#1: Dion Phaneuf

The Toronto Maple Leafs thought they had their star defenseman when the club traded for former Norris Trophy winner Dion Phaneuf. While none of the players that went to the Calgary Flames became stars, the price Toronto paid was high.

After 26 games in 2010, the Maple Leafs named Phaneuf captain. However, he would never regain the form he showed in Calgary. While Phaneuf was steady, he was not the superstar that the Leafs had envisioned when they signed him to a seven-year, $49 million contract in 2014.

The deal became a burden on the rebuilding Leafs. So, they sent Phaneuf in a mega deal to the Ottawa Senators. The Senators dumped the final two years of his contract on the Los Angeles Kings. In 2018-19, Phaneuf played in 67 games, registering six points and a minus-21 rating.

This contract possibly goes down as the worst in Toronto Maple Leafs history, given how much it held the Leafs, particularly during the infamous 2015-16 season.