Top 5 Worst Signings In Toronto Maple Leafs History

The Toronto Maple Leafs made a splash this week signing free agent Alexander Barabanov and although the signing looks good now, the team has made many mistakes over the years.

No matter what off-season it is, Toronto Maple Leafs fans are glued to their TV’s on July 1st hoping that they acquire the best free agent available.

For years, fans were hoping to acquire a top-line center like Brad Richards or Steven Stamkos, but for whatever reason the team could never win the star sweepstakes: until 2018, when John Tavares came home.

Tavares was the biggest free agent available and fans had prayed that he would leave Long Island and return to his hometown. Competing against the Boston Bruins, San Jose Sharks, Dallas Stars, Tampa Bay Lightning and New York Islanders, the Leafs were one of six teams in the hunt for the future Hall-of-Famer.

But then on July 1st, 2018 at 1:06PM, fans went nuts with one tweet:

Tavares’ dream of becoming a Leaf was about to become a reality. Twitter went nuts with over 106,000 people liking this tweet, and the fan-base was overjoyed with excitement.

Although this is an example of a good free agent signing, the Leafs are more known for the opposite. Like every other NHL team, you’re going to hit the jackpot sometimes, but also hit Double-Zero on the Roulette table more often than not.

You can have the best scouting department in the league but sometimes it doesn’t work. The player could have scored 40 goals in the NHL with another team but for whatever reason can’t perform when he gets to yours.

Also, within the Salary Cap world everything comes down to money. Two players could score 20 goals and have 60 points, but if one player is making $2 million more per season, that player will get run out of town because he should have scored 30 goals and had 75 points.

Free Agency is a blast because you expect so much out of every signing, and mediocrity is unacceptable.

However, here are the top five worst free agent signings in Toronto Maple Leafs history.

#5. Tim Connolly

Contract: Two-years worth $9 Million

After the departure of Mats Sundin in 2008, the Toronto Maple Leafs were on the hunt for a top-line center and hoped that Connolly would provide those services.

Maybe it was the hair-cut resemblance of Sundin that the Toronto Maple Leafs saw in Connolly, but this signing turned into a bust quickly.

During his two-year contract, Connolly only played one season with the Leafs, scoring 13 goals and 36 points, so he essentially was a $9 million per year player.

After his first year with the team, Connolly was demoted to the Marlies and played a total of 28 games with the Toronto’s farm system, where he ended his career.

#4. Jason Blake

Contract: Five-years worth $20 million

Blake was the definition of too good to be true when he signed with the Toronto Maple Leafs.

After coming off three consecutive 20-goal seasons, and then a 40-goal campaign with the New York Islanders, the Leafs thought they were acquiring a sniper.

However, in three seasons with Toronto, Blake scored a total of 45 goals in 216 games.

Blake was going through personal issues during his first season with the Toronto Maple Leafs having been diagnosed with chronic myelogenous leukemia, but he was still able to play a full season.

Blake’s second season in Toronto was much better as he scored 25 goals and 30 assists, but before he could finish his third season of a five-year contract, Blake was traded away to Anaheim for veteran Jean-Sebastien Giguere.

#3. Mike Komisarek

Contract: Five-years worth $22.5 million

When the Toronto Maple Leafs acquired Komisarek, they had hopes of getting a number-one defenseman who could hit, fight and score occasionally.

However, Komisarek was not the player he once was when he came to Toronto. He fought through a ton of injuries and was a liability on the blue-line.

He four seasons, he scored two career goals with the Leafs before being bought-out by the team in 2013.

#2. Jeff Finger

Contract:  Four-years worth $14 million

After playing less than 100 career games in the NHL, the Toronto Maple Leafs thought it would be a great idea to sign Finger to a four-year deal worth $3.5 million per season.

To this day, I have no idea how anyone in the organization thought this was a good idea. There’s no reason why management should have given him more than a two-year deal, and the fact that they paid him similar money to Jake Muzzin is a joke.

After signing with Toronto, Finger played less than two full seasons with the Leafs before being placed on waivers and sent to the Toronto Marlies for his final years of his contract.

Finger would never play another game professionally after his stint in Toronto.