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

5. Tim Connolly

2 year $4.75M AAV CH: 7.4%

In the 2011 Free Agency, the Leafs were in need of adding some depth to their forward group, specifically up the middle.

Their top two centers at the time were Tyler Bozak and Mikhail Grabovski. Enter; Tim Connolly who had been a high-scoring top-six center on a cup contender in recent years, scoring at a near point-per-game pace in three of the previous four seasons.

His bread and butter was his playmaking ability which should have paired well with one of the Maple Leafs’ high-scoring wingers like Phil Kessel and/or Joffrey Lupul.

The problem with Connolly was that he had a long and well documented history of injury troubles. He missed the entire 2003-04 season due to post-concussion syndrome, and all but two regular season games and the playoffs in 2006-07.

He also missed 35 games each in both 2007-08 and 2008-09. Over the two seasons before coming to Toronto, he missed 24 games in total. 

To nobody’s surprise, the contract unfortunately blew up in GM Brian Burke’s face.

Despite playing 70 games in 2011-12, he produced at the lowest rate in years scoring only 13 goals, 23 assists for 36 points.

The following year was the NHL partial season lockout. After the NHL returned to action, he was put on waivers and Connolly was assigned to the Toronto Marlies where he played 28 games and produced 12 points. When his contract expired he announced his retirement from the league at the age of 32. It is unfortunate that things did not work out for Connolly and it is always sad when players careers are cut short due to injuries.

Due to the deal being short term and having a lower caphit percentage than most contracts ahead of him on this list, it lands at number five.

4. Jeff Finger

4 year $3.5M AAV 6.1%

I remember hearing about this signing when it happened, I was out for Canada Day fireworks and my friend and his dad were making fun of the Leafs new signing, Jeff Finger. I was 10 years old and trusted in my favourite team blindly. As you might expect given the list this lands on, it did not work out for the club. 

There is a conspiracy theory that the Leafs messed up and meant to sign Finger’s Avalanche teammate, Kurt Sauer but got the two mixed up somehow. The fact this conspiracy theory even exists shows how incompetent and dysfunctional the management group at the time was. But regardless, who was Jeff Finger?

Finger was drafted in 1999 and spent years developing in College and in the minor leagues, finally getting a shot with the Colorado Avalanche during the 2006-07 season playing 22 games with them. The next year, he took on a top-four role averaging nearly 20 minutes a game and consistent penalty kill time. His play drew praise from newly appointed head coach Ron Wilson, who’s San Jose Sharks played against the Avalanche a lot being in the Western Conference with them.

In Toronto, Finger did not live up to the expectations that contract set for him. He played only 66 games in his first season, recording a career high 23 points and once again playing a top-four role, this time averaging over 20 minutes per night. The next year with a few key blueline signings and due to reported issues with Wilson, Finger played a massively reduced role limiting him to only 39 games and playing under 14 minutes per game. 

After this season, Finger would never play another NHL game after suffering a knee injury before the season and was put on waivers and sent to the minors upon recovery. He played a combined 54 games with the Marlies over the two final seasons of his deal and would never play another professional hockey game after his contract expired.

The legacy of Finger is strange and complex. On one hand, he probably should not have been given the contract he received. On the other hand, he did not live up to the expectations at all and was wrongfully thrust into a top role when he was likely more of a bottom-pair/seventh defender. Either way, he made more money than most will ever see in their lives. Taking into account the deal was not very long and at a relatively low caphit, he lands only at fourth.

3. Patrick Marleau

Three year $6.25M AAV 8.3% 

After a successful 2016-17 season that saw the Leafs make the post season for the first time in four years, the Leafs entered free agency needing to supplement their budding young core.

That young core featured up and coming talents like Morgan Rielly, Auston Matthews, Mitch Marner, William Nylander, Connor Brown, and Zach Hyman. They had some veteran assistance too but they needed more, ideally somebody with a track record of success in the playoffs to help mentor the young group and foster good habits. Ultimately, Leafs brass zeroed in on San Jose Sharks legend Patrick Marleau.

He did not have the Stanley Cup pedigree but there is no denying that Marleau had played his fair share of important games holding two olympic gold medals, two world championship gold medals and a silver as well.

In the NHL, he had amassed 177 career playoff games which included making the conference finals four times and one Stanley Cup finals appearance. His experience as a second overall pick could also make him relatable to the Leafs young core and looking back, he did clearly make an impression on the young guys as we have seen many vacation photos with Matthews, Marner, and the Marleau family over the years.

Although his 30-plus goal and near point-per-game days were long behind him, he was still a capable forward at 38 years old coming off a 27-goal 2016-17 campaign.

However, even at the time of signing the prevailing thought was that the contract would be good for a year or two but the final season it could be an albatross especially given Matthews, Marner, and Nylander would all be on new deals. 

These worries ultimately came true and after a respectable 27 goals and 47 points in 82 games his first year, there was a notable decline the second season. Aside from just appearing slower and in worse shape, he scored only 16 goals, the lowest total since his rookie year and only 37 points in 82 games.

In the playoffs it wasn’t much better as he went from four goals and five points in seven games to only two assists in seven games the following year. 

His decline mixed with the need for cap space, necessitated Leafs management to move on. The team paid the price as they shipped him off to the Carolina Hurricanes along with a first round pick in order to get out from under the deal. The price paid to get out from the deal mixed with the high cap hit, put this deal at number three. 

2. Mike Komisarek

Five year $4.5M AAV, 7.9%

When Brian Burke was hired to be GM, he had a vision; “We require, as a team, proper levels of pugnacity, testosterone, truculence and belligerence.”

Mike Komisarek was that vision personified so of course, when given the opportunity in his first free agency period, Burke moved heaven and earth to sign him. 

Unfortunately, Komisarek was not a great defender and his physical game did not translate to suppressing shots against. In fact, his high volume of penalties taken nearly made him a liability on the ice. His first season he was held to only 34 games due to a shoulder injury that required season-ending surgery.

The next year he played 75 games and despite logging nearly 20 minutes a night his first season he saw his icetime plummet averaging less than 14 minutes. 

The next season, injuries continued piling as he suffered a broken arm that required surgery, holding him to only 45 games on the year. Partially due to the lockout in 2013-13 and partially due to a freak eye injury, Komisarek played only four games for the Leafs before being waived and demoted to the Marlies.

Following that year, the team used one of their compliance buyouts granted to them from the lockout on Komisarek to cut the contract short one year. 

The fact he played less games than Marleau while being signed longer term and for the caphit being so high, this deal lands at two. Luckily, the Leafs were essentially bailed out of this contract due to the new CBA giving teams two compliance buyouts.

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?