The Toronto Maple Leafs have made some good free agent signings over the years, but the number of bad deals definitely appears to outnumber them. Here we have a list of 15 players the Maple Leafs regret or at least should regret signing. There are various reasons for making the list. Most of these players simply underachieved in Toronto or were way overpaid. And of course it could be a combination of the two.
Expectations were high when these guys signed on the dotted line with the club and it was definitely the team’s fault for paying the big bucks to several of them. Things didn’t work out exactly as planned for these players though even though some of them were bona fide NHL’ers with decent careers under their belts before and/or after playing in Toronto. But with most of them, the Leafs quickly realized their mistake and the players quickly left town or were sent to the minors.
15 Miroslav Ihnacak
Toronto spent a lot of time, effort and money helping Miroslav Ihnacak defect from Czechoslovakia in 1985 and their biggest regret was that he wasn’t as good as his brother Peter. Miroslav scored just 17 points in 56 NHL games, but the Leafs actually gave up on him too early. He was drafted 171st by Toronto in 1982 after taking Peter 25th. Peter defected and set the Leafs rookie scoring record with 66 points which lasted until this season. Miroslav, a star in his homeland, was eventually smuggled to Canada after Toronto bribed the right people. He scored in his debut, but spent most of his time in the minors. Detroit signed him as a free agent in 1988/89 and Ihnacak played one final NHL game before scoring 105 goals the next three years in the AHL.
14 Jonas Frogren
Jonas Frogren proved to be another hassle for the Leafs to sign when they inked the Swedish defenceman in 2008-09. He wasn’t really worth the trouble as he lasted just 41 games with the club and chipped in with a goal and seven points. Frogren was drafted by Calgary with the 206th pick in 1998, but decided to pass on the NHL and continue his career in Sweden. The Leafs signed him to a two-year deal as a free agent in July, 2009, but the NHL didn’t want to allow it since it wasn’t an entry-level contract. The Leafs made a mess of things and were eventually fined $500,000 and the NHL also took away a fourth-round draft pick. The contract was then allowed to stand but Frogren took off back to Sweden in April, 2010.
13 Frank Corrado
The Leafs should regret the Frank Corrado situation since they basically wasted two years of the defenceman’s career. Corrado was claimed on waivers from Vancouver in October of 2015. However, the club then let the hometown defenceman stew in the press box for 10 weeks before finally getting a chance to play. Corrado was sent to the AHL shortly after on a two-week conditioning stint and ended up playing just 39 games in 2015-16. Both sides made a mistake when Corrado signed a one-year deal in July, 2016 as he was a healthy scratch for most of the new season and was sent to the Marlies again. Corrado told the press that coach Mike Babcock didn’t like him and he played just two games before clearing waivers. He was eventually sent to Pittsburgh at the trade deadline.
12 Shayne Corson
Forward Shayne Corson was a pretty good NHL’er before joining the Leafs and his brother-in-law Darcy Tucker, but sure didn’t have the same attitude and passion the fiery Tucker displayed. Corson scored 74 points in 197 games from 2000 to 2003 and added just nine more in 32 playoff with 398 penalty minutes. The Leafs signed him as a free agent and even though he suffered from panic attacks and ulcerative colitis. Corson didn’t always see eye to eye with coach/GM Pat Quinn though. He was a healthy scratch against Philadelphia in the 2002-03 playoffs and then decided to walk out on the team. At the time, reports also called Corson a disruptive figure in the dressing room. Quinn passed on his option year and Corson joined Dallas for17 games before retiring.
11 Mariusz Czerkawski
Polish forward Mariusz Czerkawski had already played with Boston, Edmonton, the New York Islanders and Montreal by the time he signed with the Leafs as a free agent in 2005. He’d enjoyed several 20 and 30-goal seasons with those teams and the Leafs’ GM John Ferguson Jr. figured he’d take a chance on him. However, Czerkawski sat on the bench for most of the 2005-06 campaign. He ended up playing just 19 games with four goals and five points. The Leafs gave up on him by March and Boston claimed him on waivers for the remainder of the season. At the end of the season Czerkawski headed back to Europe for a couple of productive years before retiring. The Leafs signed him for just one year, but it’s still money that good have been put to better use.
10 Colby Armstrong
The Leafs obviously had a habit of signing decent NHL players who would then suddenly underachieve in Toronto. We can add forward Colby Armstrong’s name to that list. He was drafted 21st overall by Pittsburgh in 2001, but didn’t have much of a scoring touch. Armstrong played just 181 games with the Penguins before he was traded to Atlanta. When the summer of 2010 rolled around the Leafs signed him to a three-year deal worth $9 million. Armstrong didn’t play well and also missed time due to injuries, but Toronto must have expected more than the nine goals and 26 points he supplied them with in 79 games. The Leafs admitted they made a mistake by signing Armstrong and bought him out in the summer of 2012 with a year left on his deal.
9 Trevor Kidd
It was hard being a Leafs goalie for most of the last half century and poor Trevor Kidd found that out. The native of Dugald, Manitoba lasted just 34 games with Toronto from 2002 to 2004 with a record of 12-15-4. He also had a goals-against average of 3.15 with an 88.8 save percentage. Kidd was drafted 11th overall by Calgary in 1990. After four years there he spent a few seasons with Carolina and Florida before signing with Toronto as a free agent. Kidd was backup to Ed Belfour, but the Leafs didn’t really feel comfortable with him in net as his numbers show. Belfour could have used a bit more rest as he developed a back problem and Kidd went to play in Sweden during the 2004/05 lockout and then signed with a German club.
8 Stephane Robidas
The Leafs signed veteran defenceman Stephen Robidas a few years ago and then buried him on the injured list. Robidas was signed as a free agent in the summer of 2014 and even though he was 37 years old they gave him a three-year deal for $9 million. His contract won’t run out until this June. Robidas played just over 50 games with the Leafs in 2013/14 and chipped in with a goal and seven points before he disappeared. He suffered as couple of leg fractures that season and then sat out all of 2015-16 and all of 2016-17. Robidas saw the writing was on the wall and joined the club as a consultant in the front office. I suppose the Leafs figured they were paying Robidas anyway so they might as well get something out of him.
7 Philippe Dupuis
If you’re a checking centre, it’s assumed you’ll kick in with at least a few goals a year. Hell, even Matt Martin scored five times this season. This wasn’t the case with Philippe Dupuis though. He suited up for 30 games with Toronto in 2011-12 and couldn’t find the back of the net once. In fact, he didn’t chip in with an assist either. Not once did the puck bounce off his ass to a teammate for a goal which was a bit odd for a guy who once scored 108 points in junior. The Leafs signed Dupuis as a free agent in 2011 and at least had the sense to give him just a one-year two-way deal. Still, after spending the rest of the season with the Marlies, Dupuis was gone at the end of the campaign.
6 Jhonas Enroth
Toronto needed a decent backup goalie for Freddie Andersen in 2016-17 since the most games he’d played in an NHL season was 54 with Anaheim in 2014-15. Toronto settled on Jhonas Enroth and after just half a dozen games in net regretted the move. Enroth went 0-3 in his six outings with a goals-against average of 3.94 and a save percentage of 87.2. He had posted decent enough numbers as a backup earlier in his career and the Leafs gave him a one-year deal in the summer of 2016 after trading Jonathan Bernier. Enroth was put on waivers in December and sent to the AHL’s Marlies, where he hardly played. The Leafs then acquired Curtis McElhinney on waivers from Columbus in January and traded Enroth to Anaheim the very next day.
5 Tim Connolly
Tim Connolly didn’t play badly with Toronto in 2011-12 with 13 goals and 36 points in 70 games. This was below his usual output though as the former first-round draft pick had seasons of 55 and 65 points with Buffalo a few years earlier. Connolly was never a big scorer though with his career high being just goals. There’s no wonder he jumped at the ridiculous two-year, $9.5 million deal from the Leafs in July, 2011. Connolly wasn’t at his best though and had some nagging injuries. He was placed on waivers in January of 2013 when the shortened lockout season was about to face off. Of course, nobody took his contract and Connolly was sent to the Marlies. He played 28 games for the AHL affiliate and that was the end of his NHL career.
4 Mike Craig
Free agency has come a long way in the last 20 years. If you signed a group one free agent back then you had to give up a roster player as compensation. If the teams couldn’t agree on a deal the player was determined by an arbitrator, making the process quite risky. The Leafs signed forward Mike Craig from Dallas in 1994 and the Stars wanted defenceman Kenny Jonsson in return while Toronto offered forwards Grant Marshall and the late Peter Zezel. The Leafs won the case on paper, but definitely not on the ice. Craig ended up playing 172 games for Toronto and contributed 20 goals. Zezel was a far better player than Craig and had helped the Leafs reach two straight conference finals. The Leafs let Craig walk away after his dismal 1996-97 season.
3 Mike Komisarek
All Leafs fans know the Mike Komisarek saga. Toronto signed the free agent defenceman from Montreal in the summer of 2009 and gave him a five-year deal which cost them $22 million. However, he didn’t earn his money as he sat out with injuries and rarely dressed. The Leafs placed him on waivers in March, 2013 and sent him down to the AHL Marlies when he cleared them. Komisarek played 158 NHL games in the Big Smoke from 2009 to 2013 and helped out with two goals, 19 points and 169 penalty minutes. It wasn’t enough though and the Leafs bought him out in the summer of 2013. Komisarek then signed a one-year deal with Carolina for just $700,000 after Toronto had made him a rich man. He played 32 more games before retiring.
2 Jeff Finger
We can blame Cliff Fletcher for the outrageous contract offered to free agent Jeff Finger of the Colorado Avalanche back in 2008. Finger was drafted 240th overall in 1999 and had played just 94 NHL games when Fletcher knocked on his door. He was far from being an NHL star, but Fletcher offered him $14 million over four years, which was a hell of a lot of money 10 years ago. Finger contributed 33 points in his 105 games with the Leafs from 2008 to 2010. He was then placed on waivers in October of 2010 just before the season got underway. He cleared them and was sent to the Marlies where he played out the last two years of his contract. They were also the last two years of Finger’s pro career.
1 David Clarkson
Poor David Clarkson. He must be on hundreds of these lists when it comes to the Leafs worst signings, mistakes, or players etc. We sure can’t blame him for signing with the team though when Toronto lost their mind and offered him $36.75 million over seven years. That wasn’t his fault. The club was to blame and it was probably the most regrettable signing they ever made. When he wasn’t suspended or sitting in the penalty box Clarkson chipped in with 26 points in 118 games along with 185 minutes in penalties. When he was traded to Columbus in February of 2015 it was a huge mistake by the Blue Jackets and a move they also regret. Clarkson’s in the twilight zone now after playing 26 games with Columbus since the deal and sitting out all of last season.
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