What are the 15 best and the 15 worst non-entry level contracts signed by the Toronto Maple Leafs in the Salary Cap era? There is a strong argument that the latest Phil Kessel contract belongs on the Leafs worst contracts list, except that it's a great contract for the Penguins, already producing 2 Stanley Cups, 54 playoff PTS with the Leafs still paying a chunk of his annual salary. They paid him to win championships in another city. No player on a Leafs contract has had more success.
1- Phil Kessel, Oct 1 2013, 8 years $64M: Signed by Dave Nonis. This deal has won more Stanley Cups than any Leaf contract signed under the salary cap, and still has years left to pad that total. Sure, he won those Cups in a different city, but it was signed in Toronto.
2- Nazem Kadri, Apr 13 2016, 6 years $27M: Signed by Lou Lamoriello. Kadri emerged as an elite two-way player after locking in for 6 years at a very team friendly price. He could win a Selke trophy under this contract.
3- Fredrick Anderson, June 20 2016, 5 years $25M: Signed by Lou Lamoriello. Anderson has developed into an elite NHL goaltender who has been in the Vezina discussion early in this contract. We’ve seen a few talented young goaltenders come to Toronto and fall apart, but Anderson bucked that trend and delivered.
4- Tomas Kaberle, Feb 11 2006, 5 years $21.2M: Signed by John Ferguson jr. Tommy boy averaged almost 50 PTS per season under this contract and won a Stanley Cup with Boston in year five.
5- Phil Kessel, Sep 18 2009, 5 years $27M: Signed by Brian Burke. This contract produced over 150 goals and 1300 shots in 5 years. That’s good.
6- Tyler Bozak, July 6 2011, 2 years $3M: Signed by Brian Burke. 119 GP, 75 PTS and a guy who killed penalties, played the power play, and won 1190 face offs (52.6 W%). That kind of production tends to cost much more than $1.5M AAV.
7- Jake Gardiner, July 29 2014, 5 years $20.2M: Signed by Dave Nonis. His point totals over the first 4 seasons have been 24, 31, 43, and 52. He just keeps getting better. He was overpaid early but has been a bargain over the last half.
8- Matt Stajan, July 7 2008, 2 years $3.5M: Signed by John Ferguson jr. 158 GP and 112 PTS for $3.5M is a bargain. These little short-term bridge deals for RFAs can produce great value seasons. The two years of this contract produced by far the two best seasons of Stajan’s career at age 24 and 25. Stajan doubled his salary on his next contract and his production began to decline.
9- Morgan Rielly, Apr 13 2016, 6 years $30M: Signed by Lou Lamoriello. Although he had a decline in production in the first year of his new contract, he bounced back with over 50 PTS in 2018. Those are elite numbers at a fair price with plenty of time remaining.
10- Alex Steen, Feb 23 2008, 2 years $3.4M: Signed by Cliff Fletcher. He only had 4 PTS in 20 GP when they shipped him out of town for Lee Stempniak, but scored 71 PTS in 129 GP for the remainder of the contract in St. Louis (which was better than Stempniak did in Toronto). Oops.
11- Zach Hyman, July 5 2017, 4 years $9M: Signed by Lou Lamoriello. In year one he often played on the top line, scoring 40 PTS with a +22 rating at age 25. They’ve got him at a good price for what should be the prime years of his production.
12- Nik Antropov, Jun 6, 2007, 2 years $4.1M: Signed by John Ferguson Jr. The Leafs got 153 GP, 54 G, 115 PTS for $4M, which is a bargain even after accounting for cap inflation. Antropov did double his salary on his next contract.
13- Nikolay Kulemin, July 3 2010, 2 years $4.7M: Signed by Brian Burke. 152 GP and 85 PTS. This contract produced what has been the best season of his career with 57 PTS at age 24. He hasn’t even come close to that number since.
14- Nazem Kadri, Sep 10 2013, 2 years $5.8M: Signed by Dave Nonis. That’s a good price for a 2nd line center with 89 PTS in 151 GP. He came into the NHL as a scorer, but developed a strong defensive game, making him a valuable asset.
15- Clarke MacArthur, Aug 28 2010, 1 year $1.1M: Signed by Brian Burke. That’s a great price to pay for 60 PTS. He earned himself a nice pay raise on his next contract.
1- David Clarkson, July 5th 2013, 7 years $36.7M: Signed by Dave Nonis, traded to Columbus by Dave Nonis for another bad contract. He missed last season due to injury, but it was still a terrible contract prior to the injury. He was crushed by monstrous expectations. It was unfair to expect him to replicate his career year.
2- Mike Komisarek, July 1st 2009, 5 years $22.5M: Signed by Brian Burke, bought out July 2, 2013 by Dave Nonis. There should be a cap on what big, slow defensemen get paid. Granted if you needed to make a splash on defense in the summer of 2009, the options were limited.
3- Jeff Finger, July 1st 2008, 4 years $14M: Signed by Cliff Fletcher, buried in the minors by Brian Burke. There is a conspiracy theory that the team intended to sign a different player and made a mistake. That’s how bad this one was, it has its own thriving underlying conspiracy theory.
4- Tim Connolly, July 2 2011, 2 years $9.5M: Signed by Brian Burke. Year one saw a small decrease in his production from his last season in Buffalo. Year two he scored 12 PTS in 28 GP in the AHL.
5- Vesa Toskala, July 4 2007, 2 years $8M: Signed by John Ferguson jr, traded away by Brian Burke with another bad contract for another bad contract (JS Giguere). Toskala was awful after signing this contract. In his last season in Toronto before being traded he had a 3.66 GAA and .874 Sv% in 26 GP.
6- Mikhail Grabovski, Mar 6 2012, 5 years $27.5M: Signed by Brian Burke, bought out July 4 2013 by Dave Nonis. He had a very uninspiring 48 GP and 16 PTS in the lockout shortened season and Nonis used a compliance buyout.
7- Andrew Raycroft, July 4 2006, 3 years $6M: Signed by John Ferguson jr. They traded away Tuuka Rask to get this guy and then signed him to an extension. It did not work out as planned. His last season in Boston saw him put up a 3.71 GAA and .879 SV%, so Toronto had to know it wasn’t getting a great goalie. By year two of this contract, he had a 3.92 GAA and .876 SV%, so he actually got worse.
8- Joffrey Lupul, Jan 20 2013, 5 years $26.2M: Signed by Dave Nonis. In the early days of this contract it returned good value until Joff started to break down. The last 3 years have produced 101 NHL games played and just 35 PTS. Not what you paid for.
9- Matt Martin, July 1 2016, 4 years $10M: Signed by Lou Lamoriello. In year two of this contract, Martin spent much of the season watching from the press box as a healthy scratch. If any other teams were interested in acquiring this contract, he would already be gone.
10- Dion Phaneuf, Dec 31 2013, 7 years $49M: Signed by Brian Burke, traded away by Lou Lamoriello. I originally waivered on whether Phaneuf belonged on this list, but if you look at the 5 worst offensive seasons by defensemen making at least $7M AAV, there are only 2 names that repeat themselves, Brian Campbell and Dion Phaneuf.
11- Stephane Robidas, July 1st 2014, 3 years $9M: Signed by Dave Nonis. They signed a defenseman who had just broken his leg twice in the same season. He only played 52 games with Toronto before retiring due to leg issues. Who could have predicted that?
12- Jonathon Bernier, Aug 2 2015, 2 years $8.3M: Signed by Dave Nonis. In year one he had 12 Wins, 21 Losses, with a .908 SV% and 2.88 GAA. He has some difficulty stopping shots from center ice and let in many highlight reel bad goals. He was shipped out of Toronto by year two.
13- Bryan McCabe, June 29 2006, 5 years $28.8M: Signed by John Ferguson jr. I want to say that McCabe scored more goals on his own net than the other net, but that would be hyperbole. He was really good in year one, but the wheels came off in year two and he started getting the “Larry Murphy treatment” from Leaf fans. He was traded that year, but unlike Larry Murphy, did not go on to win a Stanley Cup with his new team.
14- John Liles, Jan 25 2012, 4 years $15.5M: Signed by Brian Burke. He was almost decent in year one, but by year three he was playing in the AHL and was shipped out of town for another bad contract.
15- Colby Armstrong, July 1st 2010, 3 years $9M: Signed by Brian Burke. Bought out Jun 30 2012 by Brian Burke. I want to give Colby a free pass for injury reasons, but that was a big price tag for 79 GP and 14 PTS. I think even he'd admit that. He's awesome on Hockey Central at noon. If Sportsnet gave him a 3-year deal for $9M I'd say he's worth it...