Toronto Maple Leafs 15 Best Contracts (2005-2022)

This was originally published in my 2020 book Hunting Bargains in a Salary Cap World, and has now been updated with new contracts. I will continue to update each team’s list every summer going forward. The rule is that only active contracts can move up or down. Expired deals cannot pass each other. Next summer it may even be expanded to top 20. The book is still available on Amazon, though some of the stats on active contracts are now out of date. You may yet find it interesting because there were detailed stat graphics that you won't find here. One thing you won't find here are entry level contracts because they all come from the same cookie cutter and require less skill at the negotiating table.
 
My latest book The Hockey Economist’s Betting Prospectus is now available. It's a comprehensive commentary on the last 3 years of hockey betting, broken down by team, by category, by strategy, by season. There is plenty of useful information for bettors of all skill levels. It covers pre-pandemic, peak-pandemic, post-pandemic. What worked, what failed. Lessons learned, market trends, team-by-team analysis. What impact did the pandemic have on hockey betting? The market differences between these 3 seasons are discussed at length, and there's a lot to talk about. To read more, visit the Amazon store.

If you’d like to browse my other best/worst contract lists, click here. Enjoy! 
 
Please note: The formatting on the graphics got scrambled being copied from Excel into Google Blogger. It's among the reasons my blog is looking for a new home.

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The salary cap era has been a tumultuous time for Leafs fans, making the playoffs just once in the first 11 years. Stable, successful organizations don’t need to change General Managers every 2.5 years, with all 6 guys autographing at least one of their best contracts. A majority of those best deals were signed since 2016 when the pieces of their current “contending” roster were being assembled.
 
Brian Burke was supposed to be the savior, bailing on the Anaheim Mighty Ducks not long after winning the Stanley Cup. The optimism from Leaf nation was palpable, but Burkie fell flat on his face, trading lottery draft picks for star players that failed to translate into wins. Burkie made a greater contribution to the Leafs worst contracts list than this one.
 
The Kyle Dubas administration has brough a renewal of hope, as the team peeled off 3 consecutive playoff appearances, but failed to advance beyond round 1. 2020 would prove to be a stunning failure, as Toronto failed to qualify for the post-season during what should be the peak of the Tavares-Marner-Matthews window. Dubas will be constantly battling for any penny of cap space he can find if the team is going to win a title before that window is firmly shut.
 
 
1. Phil Kessel
 

Signed By:	Dave Nonis		Position:	F
Date:	2013-10-01		Age July 1st:	26
Term:	8 years		Playoff GP:	70
Total Money:	$64M		Playoff PTS:	56
Cap Hit:	$8M		Stanley Cups:	2

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	69.2	618	497	1702
Per 82 GP	8.7	82	66	226	17.9

"Obviously I signed here to be here. I made a commitment. That's how it goes. It's hockey, right? It's a business, and you move on."

– Phil Kessel

When Phil signed this deal in Toronto, Leaf fans all around the world surely envisioned that one day he would be eating hot dogs out of the Stanley Cup, and that’s exactly what he did. This contract ranks #1 because it delivered 2 Stanley Cups to the Toronto Maple Leafs Pittsburgh Penguins. It has won more Stanley Cups than any Leaf contract signed under the salary cap, making this the team’s most successful venture by far.
 
Sure, Phil won those Cups in a different city, but it was signed in Toronto. It’s the same reason why Jeff Carter is on the Philadelphia Flyers best contracts list. Winning hardware is the best way to rise to the top of these lists, and Phil produced. If we looked only at the “bargain scale”, this one wouldn’t qualify. Kessel was considerably overpaid in at least 4 of these 6 years, and the final 2 are trending towards awful. But when you win the right to eat hot dogs out of the Stanley Cup, it doesn’t matter how much that street meat costs.
 
The best part is, Toronto agreed to continue paying part of his salary when they shipped him off to Pittsburgh, so Maple Leaf season ticket holders helped buy some of those dogs…
 
 
2. Auston Matthews
 

Signed By:	Kyle Dubas		Position:	F
Date:	2019-02-05		Age July 1st:	21
Term:	5 years		Playoff GP:	14
Total Money:	$58M		Playoff PTS:	14
Cap Hit:	$11.6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	58.4	195	252	860
Per 82 GP	11.7	82	106	362	21.0

“We understand the cap restraints we have and the league and every single team has. We want to accomplish our ultimate goal, the Stanley Cup, and make this city proud. We’re working towards that every day.”

– Auston Matthews

My original attempt to predict the free agent class of 2019 had Auston Matthews pegged for an annual salary of $14M, much closer the maximum amount allowed under the CBA. The assumption was that if he had gone to free agency, that he could have obtained whatever sum he desired, despite being restricted. We never got to find out, as he signed an extension in February, potentially taking less to get fast tracked to UFA status (yes he did sell 1 UFA year here).
 
It’s hard to say this is a discount when looking at the comparable contracts, as his basket of peers had an average adjusted year one cap hit of $9.2M. Having said that, most of those deals were incredible bargains themselves, among the best we’ve seen in the salary cap era. Optimally Dubas would have loved if Auston accepted the same terms as Jack Eichel, but the one he ultimately autographed more closely resembled Sidney Crosby circa 2007.
 
The market for unicorns like Matthews is a complicated beast to tame. Dubas was under enormous pressure to retain his RFAs heading into the summer, and getting Matthews signature on paper was critically important.
 
 
3. Nazem Kadri
 

Signed By:	Lou Lamoriello		Position:	F
Date:	2016-04-13		Age July 1st:	25
Term:	6 years		Playoff GP:	42
Total Money:	$27M		Playoff PTS:	36
Cap Hit:	$4.5M		Stanley Cups:	1

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	28.4	413	315	1181
Per 82 GP	4.7	82	63	234	17.1

"There will be growing pains. But at the end of the day, if you continue to get better, that's what is most important. The Maple Leafs logo is all I've ever known and it's all I've ever wanted to play for. So for them to show this kind of commitment meant a lot."

– Nazem Kadri

Kadri was paid almost exactly the same amount that a player with that stat line should expect, both by algorithm and a comparables search. He signed a very similar deal to Nick Bjugstad 2 years earlier, despite putting up better career numbers. Where Naz sold himself short was on term. He could have become unrestricted in the summer of 2018 if he so desired.
 
By agreeing to 6 years, he ostensibly sold 4 years where he could have gone UFA, signing away his prime earnings window. Instead he’ll hit the open market at age 31, when the offers won’t be nearly as lucrative. He may have forgone as much as $10M in career earnings. He signed this on the same day as the aforementioned Morgan Rielly deal, which turned out to be a great day for Lou Lamoriello.
 
Kadri has emerged as a very effective two-way center. Giving away those UFA years at a discount will benefit the Toronto Maple Leafs Colorado Avalanche, as the Avs acquired Nazem’s rights for Alex Kerfoot and a 1-year failed Tyson Barrie rental. They parlayed that discount into better teammates and give the Leafs Avs a better chance to win a championship. Naz earned the opportunity to participate in a parade with the Stanley Cup through downtown Toronto Colorado. Any money he left on the table was refunded by the Calgary Flames (a future contender for their worst contract list).
 
 
4. Morgan Rielly
 

Signed By:	Lou Lamoriello		Position:	D
Date:	2016-04-13		Age July 1st:	22
Term:	6 years		Playoff GP:	34
Total Money:	$30M		Playoff PTS:	24
Cap Hit:	$5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	31.5	418	281	1021
Per 82 GP	5.3	82	55	200	23.0

“I have a long way to go, a long way to improve and for me, I'm just looking forward to the challenge. I want to get better and move forward with this team."

– Morgan Rielly

Morgan Rielly had just completed a 36-point season at age 21 when he inked this treaty in April 2016. It closely resembled the Justin Faulk deal from 2 years earlier, and set the market for Seth Jones and Hampus Lindholm to follow a few months later.
 
Although Rielly suffered a production decline down to 27 PTS in year one, he bounced back with 52 and 72 PTS in years two and three. He was on his way to another bargain season in year four before suffering an 8-week injury that extended into the Covid shutdown. Getting a top pair defenseman with this much offensive upside for this price is crucial to this team being able to afford its high-priced forwards. He received a $60M extension from the Leafs when this expired.
 
 
5. Tomas Kaberle
 

Signed By:	Turd Ferguson		Position:	D
Date:	2006-02-11		Age July 1st:	28
Term:	5 years		Playoff GP:	25
Total Money:	$21.3M		Playoff PTS:	11
Cap Hit:	$4.3M		Stanley Cups:	1

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	33.2	377	238	664
Per 82 GP	6.6	82	52	144	23.7

"Tomas represents a core part of our organization and we rely on him to play in all situations. Tomas figured to be one of the young premier free agents in the off-season and we are pleased that he is committed to being a big part of our future success."

– John Ferguson

Kaberle was set to become an unrestricted free agent on July 1st and instead agreed to an extension in February. He finished that season at 28-years-old with 67 PTS, which for a defenseman should translate to a big pay day. Teammate Bryan McCabe signed 4 months later for substantially more money despite having a nearly identical stat line.
 
Tommy Boy scored 52 PTS per 82 GP under this contract and won a Stanley Cup with Toronto Boston in year five. The Leafs received Joe Colborne, a 1st round pick and a 2nd round pick in the trade, which is a nice haul. The good news is that one of those picks turned into Rickard Rakell, the bad news is they flipped the pick to Anaheim to move up in the round and take Tyler Biggs. Kaberle’s scoring rate did decline over time as he turned 30 at the halfway mark of the deal. A hand injury in 2009 contributed to his worst season of the five, where he only scored 31 PTS.
 
 
6. Phil Kessel
 

Signed By:	Brian Burke		Position:	F
Date:	2009-09-18		Age July 1st:	21
Term:	5 years		Playoff GP:	7
Total Money:	$27M		Playoff PTS:	6
Cap Hit:	$5.4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	36.1	364	333	1383
Per 82 GP	7.2	82	75	312	20.0

“The Kessel acquisition was in large part because I thought we had some ticket price fatigue. Well, ok, if we’re not going to win, let’s at least have a star player for what we charge for tickets. And Phil did a good job here and worked out fine. People don’t like him, but that’s fine.”

– Brian Burke

Phil Kessel completed his Entry Level Contract in Boston in 2009, going unsigned throughout the summer and into training camp. Brian Burke, the newly hired General Manager of the Toronto Maple Leafs was kicking tires on what he saw as a franchise type player at the foundation of his rebuild. Burke pulled the trigger and sent a pair of first round picks to acquire the sniper, then signed him to this ticket shortly thereafter.  The Leafs gave him 1 more year and $1.4M more per season than what the Bruins had been reportedly offering. My algorithm and comparables basket both had expected salaries in the $6M range, which is very close the Bruins offer (after adjusting for cap inflation).
 
Phil the Thrill was overpaid at the start of this deal at age 21 when he scored 55 PTS, but grew into a bargain scoring 82 PTS in year three. This contract produced over 150 goals and 1300 shots in 5 years. That’s outstanding. The downside is that Phil was -46 and only played 7 playoff games over a 5-year period where Brian Burke had expected them to be contenders. The lack of team success turned the draft picks Burke traded away into Tyler Seguin and Dougie Hamilton. Ouch.
 

7. William Nylander
 

Signed By:	Kyle Dubas		Position:	F
Date:	2018-12-01		Age July 1st:	22
Term:	6 years		Playoff GP:	21
Total Money:	$41.8M		Playoff PTS:	18
Cap Hit:	$7M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	42.3	254	208	716
Per 82 GP	7.0	82	67	231	17.3

"I think at the end it becomes a little bit frantic when you go right down to the deadline at the very end and you're trying to make sure everything gets in"

– Kyle Dubas

The Leafs made every effort to minimize Nylander’s pay day, knowing that Marner and Matthews needed new deals the following summer. Dubas decided to play hardball, leading to a hold-out that lasted deep into the season. In past years comparable centers more regularly accepted shorter bridge deals, especially at an age when they have no arbitration rights.
 
Nylander had no interest in signing a bridge because he did not want it to expire after the other stars had new pacts, when the team would be more cap crunched. That may not have been the best outcome for the team, but it was the optimal path for Nylander to personally follow. This was a win for him. This deal had a similar term and adjusted cap hit to Nathan MacKinnon, to which you could say “he’s not worth MacKinnon money”, however that’s also one of the grossest underpayments in the entire salary cap era.
 
That 60-point stat line should have been worth closer to $6M. The first year was a disaster. Willy didn’t suit up until December, his scoring rate plummeted and he found himself in Leaf Nation’s doghouse. He rebounded nicely in year two, scoring at a 70-point clip which is easily worth the price they paid him.

 
8. Zach Hyman
 

Signed By:	Lou Lamoriello		Position:	F
Date:	2017-07-05		Age July 1st:	25
Term:	4 years		Playoff GP:	21
Total Money:	$9M		Playoff PTS:	6
Cap Hit:	$2.3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	9.4	247	151	513
Per 82 GP	2.3	82	50	170	18.0

"Hyman is a guy who gets the puck back all the time. I've learned from good players - they like to have the puck. When you have three guys who want the puck - like (Pavel) Datsyuk used to tell me all the time, 'No, put him on somebody else's line. I want somebody to get me the puck.' He gets the puck back better than anyone."

– Mike Babcock

Zach Hyman inked this ticket at the conclusion of his ELC after scoring 28 PTS and his compensation was right on par with what a player with those numbers should have banked. The only uncommon component is the 4-year term, when 2-years would have taken him to unrestricted free agency. It had to be an easy decision for Hyman, who had under 100 games of NHL experience attained. Selling UFA years had to be the least of his concerns.
 
Hyman became an effective complementary player in the Leafs top 6 forwards, doing some of the dirty work for their high-end offensive players. Hyman scored 50 PTS per 82 GP, averaging 18 minutes per game. He was producing in the $4M range while getting paid $2.3M, though some of that might be due to his linemates, playing most of his 5 on 5 minutes with Marner, Tavares, or Matthews. There are plenty of scrubs in the NHL who could have replicated Hyman’s numbers if they got to play that much with those teammates (like Michael Bunting). 
 
 
 9. Michael Bunting
 

Signed By:	Kyle Dubas		Position:	F
Date:	2021-07-28		Age July 1st:	25
Term:	2 years		Playoff GP:	6
Total Money:	$1.9M		Playoff PTS:	3
Cap Hit:	$962K		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	1.9	79	63	175
Per 82 GP	1.0	82	65	182	15.5

"It all comes down to value"

– Kyle Dubas

Michael Bunting got to visit the unrestricted free agent market before turning 27 via “group 6” status, and he decided to take his talents to Toronto after just 26 career NHL games. Bunting was born in Toronto and Kyle Dubas was his GM in the OHL, so the two had a history. It’s very likely that he was told that he could get the opportunity to play with Marner and/or Matthews as he was widely seen as a cheap replacement for the departing Zach Hyman.
 
Play on the top line he did, scoring 63 PTS in year one and providing roughly $5M of value for under $1M in cap hit. That’ a fantastic price-point, but also there are a lot of players who could have been plugged into that opportunity and scored just as many points, so don’t necessarily expect Bunting to get anywhere near $5M on his next deal.
 

10. Tyler Bozak
 

Signed By:	Brian Burke		Position:	F
Date:	2011-07-06		Age July 1st:	25
Term:	2 years		Playoff GP:	5
Total Money:	$3M		Playoff PTS:	2
Cap Hit:	$1.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	3.8	119	75	170
Per 82 GP	1.9	82	52	117	19.4

"If we have Tyler Bozak in the one hole and he can't play in the one-hole, that is my fault, not Tyler's."

– Brian Burke

Tyler Bozak had accumulated 119 games of NHL experience when he agreed to this pact. The numbers he produced had an expected free agent value over $3M, according to both my algorithm and comparables search, projecting 2-3 years at around $3.6M. Burke got him for nearly half that and was surely able to cite his lack of tenure at the negotiating table. A quality stat line is less valuable if it hasn’t been replicated over a longer period of time. The good news for Tyler, he was set to be unrestricted when this expired and his scoring jumped substantially in the first year, proving those early positive indicators were correct.
 
While Bozak might have been a divisive figure over his tenure with the Maple Leafs, there is no question that this contract provided considerable value. He’s a center who averaged nearly 20 minutes of ice time per game, scored 52 PTS per 82 GP, played both power play and penalty kill, and won 1190 face offs (52.6 W%). That’s the equivalent of getting a $5.9M player for $1.9M. Bozak would go to market when this expired, ultimately deciding to return to Toronto with a 5-year deal at $5.3M (adjusted), at which point in time he began to draw the ire of cap conscious fans.
 
Realistically some of that money should have been deposited into Phil Kessel’s bank account. It’s unlikely that Bozak would ever have produced nearly that much offense without Kessel flying up and down his wing.
 
 
11. Jake Gardiner
 

Signed By:	Dave Nonis		Position:	D
Date:	2014-07-29		Age July 1st:	23
Term:	5 years		Playoff GP:	20
Total Money:	$20.3M		Playoff PTS:	7
Cap Hit:	$4.1M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	22.8	384	180	560
Per 82 GP	4.6	82	38	120	21.4

"He's clearly still improving. This isn't a player who has reached his ceiling yet. There's a lot more for Jake to give. He's already a very good player. ... We think there's a chance he could improve dramatically over the five-year period."

– Dave Nonis

Jake Gardiner played 167 games on his ELC and averaged nearly 32 PTS per 82 GP and 21.3 minutes of average ice time. The agreed upon wage to retain his services was reasonably close to the expectations of that production level, and was structured similarly to deal signed by his closest comparable John Carlson from 2 years earlier.
 
Jake was slow out of the gate with just 24 PTS in year one, but gradually improved and peaked at 52 PTS in year four. In a perfect world, Gardiner would have hit the UFA market that summer. A back injury derailed the final year and ultimately limited what he was able to attain in free agency.
 
Gardiner was supposed to be one of the best UFA defensemen available, went unsigned into September, and received far less money than people expected. We witnessed a similar situation with Cody Franson a few years earlier. The reluctance of GMs to sign him to a big pay day has been proven smart, as his new career in Carolina is off to a terrible start.
 
 
12. Frederik Andersen
 

Signed By:	Lou Lamoriello		Position:	G
Date:	2016-06-20		Age July 1st:	26
Term:	5 years		Playoff Wins:	8
Total Money:	$25M		Playoff SV%:	0.911
Cap Hit:	$5M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	5.3	268	149	2.79	0.914

"I think that he has to know that he's our No. 1 goaltender and that the support is there, the confidence is there and the commitment's there"

– Lou Lamoriello

Lou Lamoriello took a big risk sending 1st and 2nd round draft picks to Anaheim to acquire Andersen and it has paid off, even though those picks turned into Sam Steel and Max Comtois. They signed this deal on the day the trade was made. Andersen was generously compensated for the stat line, agreeing to similar terms as Jaroslav Halak received 2 years earlier.
 
This investment wasn’t exactly as safe a bet as it might seem in hindsight, and there were certainly naysayers at the time. He had only accumulated 125 career games and had yet to prove that he could handle the load that Lou was expecting him to play. Some of the ghosts in Toronto’s goalie graveyard made that same transition from California to Ontario lacking experience with disastrous results (including the guy he replaced as Toronto’s #1 netminder) that you can read about on the Leafs worst contracts list.
 
Freddy has developed into an elite NHL goaltender who was in the Vezina discussion early in his Toronto tenure. We’ve seen a few talented young goaltenders come to Toronto and fall apart, but Anderson bucked that trend and delivered. The returns on the front half were undeniably bountiful, Andersen began to struggle after his 30th birthday in year four. That could have been due to the coaching change, with Keefe taking more risks on offense, leaving Freddy out to dry. As steadying an influence as he provided in the regular season, it did not translate into playoff success.
 
 
13. Matt Stajan
 

Signed By:	Cliff Fletcher		Position:	F
Date:	2008-07-07		Age July 1st:	24
Term:	2 years		Playoff GP:	0
Total Money:	$3.5M		Playoff PTS:	0
Cap Hit:	$1.75M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	5.1	158	112	246
Per 82 GP	2.5	82	58	128	17.9

"You've just got to keep a level head and come to the rink with the same attitude every day to work hard, to help your team win. Just let everything else kind of happen around you. Only control what you can control on the ice.”

– Matt Stajan

Stajan entered restricted free agency as a 30-point player at age 24 when his approximate expected salary should have been north of $3M (adjusted). This was already a low price for the stat line, and would become an even larger underpayment when he started producing like a $6M player.
 
This investment returned tremendous value, scoring 58 PTS per 82 GP, averaging almost 18 minutes per game of ice time. 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.
 
Before this term came to an end, Stajan was traded to Calgary as part of the Dion Phaneuf trade, where Stajan was paired with Jarome Iginla. His scoring pace did drop in the 27-game audition provided in Calgary before this deal expired. One month after the trade, Calgary extended him a further 4 years, nearly doubling his salary. Stajan was set to become an unrestricted free agent, so the Flames had to pay him accordingly if they wanted to retain his services. They didn’t acquire him in the Phaneuf trade to watch him walk a few months later. Unfortunately, that might have been the best outcome, as his production immediately began to decline, which you can read more about on Calgary’s worst contracts list.
 
 
14. Ian White
 

Signed By:	Turd Ferguson		Position:	D
Date:	2007-05-08		Age July 1st:	23
Term:	3 years		Playoff GP:	0
Total Money:	$2.6M		Playoff PTS:	0
Cap Hit:	$850K		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	3.9	235	85	447
Per 82 GP	1.3	82	30	156	21.4

“He’s recognized and readily admitted that he’s made a mistake. He’s committed to making sure of making better decisions going forward.”

– John Ferguson

Ian White was a promising prospect who was charged with DUI in September 2006 prior to his rookie season. Despite his legal infraction, he made the team, who stood behind him throughout the process. It’s easy to imagine why he was receptive to a 3-year deal for 30 cents on the dollar for what he should have been worth. Teammate Carlo Colaiacovo signed for more than double the amount despite a less successful performance.
 
During the best season of his career (where he would finish with 38 PTS), White was traded to the Calgary Flames as part of the Dion Phaneuf trade. The Flames retained him for one more season as an RFA for more money than he made over these 3 years combined.
 
 
15. Mats Sundin
 

Signed By:	Turd Ferguson		Position:	F
Date:	2007-06-12		Age July 1st:	36
Term:	1 year		Playoff GP:	0
Total Money:	$5.5M		Playoff PTS:	0
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	9.0	74	78	259
Per 82 GP	9.0	82	86	287	20.1

"I feel at the start of this season, we have as good of a chance as Anaheim or Ottawa or any other team to win the Stanley Cup"

-Mats Sundin

Mats Sundin was captain of the Maple Leafs and one of the best players in team history after more than a decade of service. The Swedish center still managed to score above a point per game pace at age 35, and probably could have successfully demanded a longer-term deal than what he received, but since he was nearing retirement, Mats decided to take it one year at a time, like fellow countryman Nick Lidstrom.
 
The price wasn’t cheap, but the team got what they paid for, with Mats scoring 32 goals and 78 PTS, surpassing his output from the previous season. Afterwards he would once again flirt with the concept of retirement, but eventually was enticed to join the Vancouver Canucks for a substantial fee.