The Toronto Maple Leafs have a lengthy history of trying to make a big splash in the free agent market. Sometimes it works out really well for the team, other times those signings end up being a mistake. But what free agent signings for the Leafs ended up being total disasters?
Former Maple Leafs defenseman Conor Timmins signed a two-year deal this week, with a $2.2 million AAV, which sent the internet into a buzz.
Timmins played 101 games with the Toronto Maple Leafs from 2022-2025 and was the definition of a seventh defenseman. The right-shot defenseman had good size, which was much needed on Toronto's blue line, but he provided virtually zero offense. In my opinion, he was a fine depth player who you'd want in your organization, but after signing in Buffalo, it feels like Leafs fans feel the opposite way.
If you go on social media, fans are calling the Sabres a joke for signing Timmins to a two-year deal that doubled his salary, calling it one of the worst signings of all-time.
Speaking of terrible signings, the Timmins deal got me thinking about Toronto's free agent history. Over the 100-plus history, the Leafs have made some great deals, but they've also made some terrible ones. Although this offseason was good, there are plenty of examples of when it was bad.
As such, let's breakdown the worst three signings in Leafs history.
3) Nick Ritchie
When the Leafs signed Nick Ritchie, I saw the vision. He was a 6-foot-3, 235 pound winger who seemed like the perfect Zach Hyman replacement. With so much size, Ritchie seemed like a player who could go fetch pucks in the corners, then be the beneficiary to Auston Matthews and Mitch Marner.
However, that experiement failed quickly and you could tell that Ritchie was not up for the job. In 33 games with the Leafs, Ritchie scored two goals and looked lost on the ice. His size seemed optimal beside Toronto's top forwards, but unfortunately he lacked speed so he couldn't keep up.
As much as this signing was terrible, the reason it's not higher on the list is because the Leafs found Hyman's replacement in Michael Bunting right after the Ritchie experiement failed, and then they were also able to acquire Ilya Lyubushkin in exchange for Ritchie. So although he didn't work out, the rest of the team fell into place once they realized he wasn't working.
Kudos to Kyle Dubas for rectifying his mistake pretty quickly because it would have been easy to keep him with the team, trying to force it work. However, he recognized his failure and moved on, ulltimately acquiring a defenseman who really helped the team.
2) David Clarkson
If you read the headline to this article, you probably would have assumed that Clarkson would be No. 1 on this list, but he ultimately falls at No. 2. I'm almost shocked that ESPN hasn't produced a 30 for 30 on David Clarkson's tenure with the Leafs yet, because it's so facinating.
Coming off a 30-goal season with the New Jersey Devils, Clarkson signed a seven-year deal with the Leafs, at $5.25M AAV. The Toronto, ON native was coming home and looked like he could become the next Wendel Clark or Darcy Tucker, as someone who's legacy would live on in the city for years to come.
I guess that ultimately became true but all for the wrong reasons as Clarkson's game went sideways. It started with a 10-game suspension by coming off the bench to fight, then continued to tailspin from there. Clarkson scored five goals and registered 11 points in his first season with the Leafs. Things didn't get much better in Year 2, as Clarkson finished with 10 goals and 15 points before getting shipped to Columbus for a salary-dump of Nathan Horton.
Similarly to Nick Ritchie's contract, the Clarkson situation could have been much worse as they were somehow able to get out of that deal, despite it having five years remaining. Clarkson was supposed to bring new life to the organization, but instead made them a joke once again.
1) Jeff Finger
The Jeff Finger signing is not only one of the worst/funniest signings in Leafs history, but it has to be one of the worst in NHL history. Finger signed a four-year deal worth $14M, but only played 105 games before being summoned to the American Hockey League.
Every executive is going to sign a free agent who doesn't live up to expectations, but how many GM's sign a player who isn't the player they meant to sign? If you look back to July, 2008 when the Leafs signed Finger, Dan Tolensky of HockeyBuzz.com wrote a tremendous article outlining that he thought the Leafs signed Finger by mistake.
Tolensky pointed out that he thinks that former Leafs GM Cliff Fletcher meant to sign Kurt Sauer but signed Finger by mistake. Both Sauer and Finger played on Colorado at the time, and based on the quotes and money that Finger recieved, he was almost certain that Fletcher thought he was signing Sauer, who was a shutdown defenseman, but instead got Finger.
Imagine being Finger's agent when the Leafs offer him $14M? Finger was ranked as the 199th best defenseman in the NHL heading into free agency, but somehow hit the lottery because Fletcher got his Avalanche defensemen messed up.
This is hands down one of the worst signings in NHL history.