What are the 10 best and the 10 worst 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 worst contracts list, except that it's a great contract for the Penguins, already producing 45 playoff PTS in 2 years with the Leafs still paying a chunk of his annual salary. Because it has been a great contract for the Penguins I must exclude it from the worst contracts list. Entry level contracts not included.
1- 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.
2- Nik Antropov, Jun 6, 2007, 2 years $4.1M: Signed by John Ferguson Jr. Anytime you can get 153 GP, 54 G, 115 PTS for $4M, you’re doing fantastic. Antropov did double his salary on his next contract.
3- 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.
4- 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.
5- 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. 50 PT defensemen tend to cost a lot more than $4M AAV.
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- 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 over the following 6 seasons.
8- 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.
9- 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.
10- Morgan Reilly, 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, many still believe he’s got a bright future. If he doesn’t start trending in the opposite direction soon, this contract should not be on this list.
WORST (ordered by the amount of money)
1- 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. The Clarkson contract is arguably worse than this, but I decided to rank these by total dollars spent.
2- 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 my monstrous expectations. It was unfair to expect him to replicate his career year.
3- 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.
4- 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.
5- 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.
6- 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.
7- Tim Connolly, July 2 2011, 2 years $9.5M: Signed by Brian Burke. Year 1 saw a small decrease in his production from his last season in Buffalo. Year 2 he scored 12 PTS in 28 GP in the AHL.
8- 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?
9- 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.
10- 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.
*- 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...
PS: Toronto is a team that I could very easily made a top 20 worst contracts. There's a bunch more bad ones, I just capped it at 10. At least when I did the Rangers I did the 20 worst contracts. I could not narrow that list down to just 10.