Toronto Maple Leafs 15 Worst Contracts (2005-2022)

This was originally published in my 2020 book The Definitive Guide to Salary Mismanagement, 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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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.
 
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 main theme of the Toronto Maple Leafs worst contracts list is “the Quest for Truckulence”, a word often used by Brian Burke to describe the type of players he prefers to have on his roster. Brian may have been heralded as the potential savior of a desperate fan base at the time he was poached from Anaheim, a sentiment that had long since vanished by the time he was fired 5 years later.
 
Burke and his successor Dave Nonis shared this common vision. Nonis was Burke’s former assistant/apprentice, and had played a contributing role in many of his boss’s bad decisions. The two inked a majority of the deals on this list, and many of those calamities involved over-paying for toughness. Lou Lamoriello may not have been Burke’s apostle, but also placed extra value on grit and had a history of giving too much term to older players..
 
 
1. Dion Phaneuf
 

Signed By:	Dave Nonis		Position:	D
Date:	2013-12-31		Age July 1st:	29
Term:	7 years		Playoff GP:	23
Total Money:	$49M		Playoff PTS:	6
Cap Hit:	$7M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	53.5	368	123	652
Per 82 GP	7.6	82	27	145	20.9

"If you look at his numbers since he was a rookie, they stack up very favourably with the top defencemen in the league. He's a player that is getting better and a player we can build around to be a contender."

– Dave Nonis

Dion Phaneuf was set to become an unrestricted free agent, and Dave Nonis would only be to retain him with a big pay day, a player representing the personification of truckulence. Dion might have been worth this salary a few years earlier, but 2014 saw his scoring production drop (from 48 to 32 PTS per 82 GP) and Nonis extended him in the middle of that season, while the depreciation was occurring. Had this been 4 years at $5M, it would have been a reasonably defensible deal.
 
Phaneuf’s worst full season in Calgary saw him score 47 PTS, while his best season in Toronto produced 44 PTS. That being said, none of his best seasons in Toronto came under this contract, which was bad from day one. Dion only lasted one full season in Toronto under this treaty before being shipped to rival Ottawa in a mutual salary dump with the Leafs retaining 25% of the salary.
 
I’m reminded of the scene in Moneyball when Billy Beane tells David Justice, “that’s what the New York Yankees think of you. They’re paying you $3.5M to play against them.” In return, the Leafs got saddled with 3 awful Senators contracts. Dion helped the Senators advance to a conference final before being dumped on the LA Kings, who would eventually buy out the final 2 years. He did help me win a fantasy hockey championship in 2018 before his production fell off a cliff, so he’s got that going for him…
 
 
2. Mike Komisarek
 

Signed By:	Brian Burke		Position:	D
Date:	2009-07-01		Age July 1st:	27
Term:	5 years		Playoff GP:	0
Total Money:	$22.5M		Playoff PTS:	0
Cap Hit:	$4.5M		Stanley Cups:	0

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	30.1	158	19	118
Per 82 GP	6.0	82	10	61	15.9

“We know that he will bring his hard-nosed approach to our team on a consistent basis.”

– Brian Burke

If we’re talking about General Managers who failed to read the tea leaves on the direction the game was heading, Brian Burke’s acquisition of Mike Komisarek is a definitive example. The quest for truckulence produced disastrous results. Burkie sought to create a big splash on the free market in the summer of 2009 when the Leafs desperately needed to upgrade their defense. The problem was, there were very few decent options available that summer. The expectation for comparable free agents was 3 years in the $3M range, and this lumbering dinosaur landed 5 years for double the expected salary.
 
Komisarek was a dud on arrival in Toronto and would eventually be bought out. This calamity helped teach NHL General Managers to be careful how much money they award to big, slow defensemen (well except Lou Lamoriello, who made a comparable mistake on Anton Volchenkov a year later). This type of player has been slowly phased out of existence in a league that has been evolving towards speed and puck moving. Defenders who lack footspeed have become a greater liability in the new NHL. Brian Burke was blind to that trend, contributing to his demise as GM of the Leafs.
 
 
3. David Clarkson
 

Signed By:	Dave Nonis		Position:	F
Date:	2013-07-05		Age July 1st:	29
Term:	7 years		Playoff GP:	0
Total Money:	$36.8M		Playoff PTS:	0
Cap Hit:	$5.3M		Stanley Cups:	0

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	41.6	144	30	221
Per 82 GP	5.9	82	17	126	13.6

"I believe that he's got a lot of good years left in him."

– Dave Nonis

Some of you were probably expecting David Clarkson to be #1 on this list, as he was in the conversation among pundits as one of the worst contracts of the previous decade. The magnitude of this catastrophe would have been far greater had the last 4 years not been stashed on IR. Clarkson had produced a career year in 2012 playing with Zach Parise that saw New Jersey advance to the Stanley Cup final, following that up with a 41-point pace in the lockout shortened season before hitting the UFA market. Brian Burke had been fired a few months earlier and Nonis had to be eager to put his stamp on the roster and prove himself a worthy successor to his mentor. He threw a bone to those in Leaf nation who yearn for greater truckulence, failing to account for the fact that the heavy hitters tend to depreciate more rapidly.
 
Realistically this should have been 3-5 years in the neighborhood of $4M (adjusted for cap inflation). Even that would have been too much money for what he would eventually produce, but it’s closer to what the market dictates for players with similar statistics. David’s first season in Toronto might have been the single worst opening season for a prized free agent we have seen in the last 15 years. Few have ever deflated this fast. Was he simply crushed by monstrous expectations? Well he never got a chance to redeem himself, as Nonis traded him to Columbus in year two in exchange for Nathan Horton, who had already suffered a career ending injury. That made sense for the Blue Jackets, who had failed to buy insurance on the Horton deal and were on the hook to pay him not to play. Clarkson conveniently suffered his own career ending injury shortly thereafter, which was covered by insurance. This could have been so much worse had they not been saved by LTIR.
 
 
4. Jeff Finger
 

Signed By:	Cliff Fletcher		Position:	D
Date:	2008-07-01		Age July 1st:	28
Term:	4 years		Playoff GP:	0
Total Money:	$14M		Playoff PTS:	0
Cap Hit:	$3.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	19.5	105	33	97
Per 82 GP	4.9	82	26	76	18.0

“Jeff is a player that will bring a much needed physical element to our team. He showed tremendous improvement in his game last season and he plays a strong positional game at both ends of the ice.”

– Chuck Fletcher

Jeff Finger had accumulated fewer than 100 NHL games when Cliff Fletcher pushed his chips to the middle and made one of biggest head scratching July 1st UFA offers in recent memory. Even knowledgeable fans could be forgiven if they had no idea who this guy was. A comparable stat line would be worth closer to $3M, but generally 28-year-old UFAs tend to have played over 100 career games.  A 2-year offer for $2M AAV would have been an appropriate bid, probably far more than Finger was expecting.
 
There is a popular conspiracy theory online that Cliff Fletcher didn’t actually know who Jeff Finger was and signed this contract thinking he was someone else. The case of mistaken identity must have extended into year one, when Toronto played him over 20 minutes per game. The coach may have just felt an obligation to play the new acquisition given the size of the investment. Finger was eventually buried in the minors by Brian Burke, which marked the end of his NHL career. With $14M in the bank, I’m sure he’s had a very satisfying post-retirement life.
 
 
5. Mikhail Grabovski
 

Signed By:	Brian Burke		Position:	F
Date:	2012-03-06		Age July 1st:	28
Term:	5 years		Playoff GP:	7
Total Money:	$27.5M		Playoff PTS:	2
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	33.3	48	16	80
Per 82 GP	6.7	82	27	137	15.6

“I always wanted to be in a place where people believed in me and gave me a chance to play. It was very important for me to stay in Toronto”

– Mikhail Grabovski

Mikhail Garbovski hit his apex in 2011 scoring 58 PTS and was set to become an unrestricted free agent in the summer of 2012 before a possible work stoppage. Burke decided it would be prudent to lock-up the center with a generous deal ($1.6M above expected value) before the players were locked out. Brian was fired shortly after the new CBA was signed and wouldn’t get to stick around to watch Grabo stumble out of the gate, scoring an abysmal 16 PTS in 48 GP, forcing predecessor Dave Nonis to buy out the pact after a single season.
 
Grabovski took a major step backwards in year one, as his scoring rate was cut in half. The good news for the Leafs is that the buyout would not count against their future salary cap, as it was a “compliance buyout” as part of the new CBA. Had that option not been available, the team likely would have let this play out longer. Grabovski’s career after this was maligned by injuries, as he never again came close to scoring 50-points. This should have marked the end of his optimal earnings window, yet there was still a 4-year $20M covenant coming from the Islanders 2 years later that you can read about on their worst contracts list.
 
 
6. Patrick Marleau
 

Signed By:	Lou Lamoriello		Position:	F
Date:	2017-07-02		Age July 1st:	37
Term:	3 years		Playoff GP:	14
Total Money:	$18.8M		Playoff PTS:	7
Cap Hit:	$6.3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	19.7	164	84	364
Per 82 GP	6.6	82	42	182	16.7

"You only have one chance to do something like this and we would not have done it if it was not the right player”

– Lou Lamoriello

Patrick Marleau decided to test unrestricted free agency at age 38 after scoring 46 PTS with the San Jose Sharks, marking 3 consecutive years of decline from the 70 PTS he scored in 2014. Contracts given to players over the age of 35 have the ominous feature that they continue to count against the cap if the player retires before it expires. For this reason, 95% of all contracts signed by players in this demographic are 2 years or less, with 74% being exactly 1 year. Lou Lamoriello decided Marleau was a safe enough bet to continue playing until age 40, and handed out a ridiculous term.
 
At this stage in his career, Marleau was not worth much more than $4M, even 1 year at $5M might have been excusable. History would have judged this acquisition much differently had it been 2 years $4M. The 3rd year would eventually become a massive problem as it overlapped with Marner, Matthews, and Nylander needing new deals. To make matters even worse, they gave him a full no-trade clause that drastically limited their options when they needed to unload him. Lou Lamoriello wasn’t looking far enough down the road, creating an untenable cap crunch for Kyle Dubas, who had to trade a 1st round pick to dump the deal on Carolina, who bought it out.
 
 
7. John Tavares
 

Signed By:	Kyle Dubas		Position:	F
Date:	2018-07-01		Age July 1st:	27
Term:	7 years		Playoff GP:	15
Total Money:	$77M		Playoff PTS:	11
Cap Hit:	$11M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	77.8	280	274	883
Per 82 GP	11.1	82	80	259	18.7

“I believe that this team has got such a great opportunity, and not just for the first few years of my contract. For me, what was important was all seven years, to really believe that there was a big window here to win and to be a part of something special, and to be from here, you start to get those emotions coming. It just felt right.”

– John Tavares

If Dubas had signed John Tavares to a 7-year contract at an $8M cap hit, then this would be on the Leafs best contracts list instead. I actually had this deal on earlier versions of the Leafs best contracts, thinking it could lead to a Stanley Cup, at which point cap hit wouldn’t matter. Problem is, for the first four years, Toronto did not win a single playoff series despite a superstar roster, because those bright shiny stars cost so much money the team could not afford the quality roster depth required for post-season success.
 
Meanwhile, the team that Johnny abandoned (the New York Islanders) had multiple playoff runs that J.T had to watch from the golf course. He was close to a point per game player for the first four years, and that’s awesome, but $11M is just a bad price-point.
 
 
8. Darcy Tucker
 

Signed By:	Turd Ferguson		Position:	F
Date:	2007-02-27		Age July 1st:	32
Term:	4 years		Playoff GP:	0
Total Money:	$12M		Playoff PTS:	0
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	17.8	74	34	152
Per 82 GP	4.5	82	38	168	16.4

“I can’t see myself playing anywhere else. As far as I’m concerned, I want to remain a Maple Leaf.”
– Darcy Tucker

Darcy Tucker was a feisty competitor who had become a fan favorite during his 6-year tenure in Toronto, reaching a career high 61 PTS in the season following the 2005 lockout. Despite missing time with a knee injury during his free agent season, scored at a 60-point pace when healthy. Tucker needed a new deal at age 32 and Ferguson extended him a further 4 years before he had a chance to hit the open market. The price paid was fair given the stat line, unfortunately his scoring rate fell dramatically in year one from 63 to 38 PTS per 82 GP. Ferguson was fired less than a year after authorizing this agreement, and his successor bought out the remainder a few months later.
 
The decline in production should not have come as much of a surprise given his age and the many hard miles on his odometer. Giving extended term over the age of 30 to this type of player is an unnecessarily risky investment. While the Leafs might have been disappointed with the 34 PTS he scored in 2008 before the buyout, that level of production was very consistent with the rest of his career. Maybe they didn’t get what they paid for, but the end result was eminently predictable.
 
 
9. Vesa Toskala
 

Signed By:	Turd Ferguson		Position:	G
Date:	2007-07-04		Age July 1st:	31
Term:	2 years		Playoff Wins:	0
Total Money:	$8M		Playoff SV%:	0.000
Cap Hit:	$4M		Stanley Cups:	0

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	5.8	85	31	3.33	0.887

"There was an element of risk but nothing we weren't comfortable with. That was always our intention to negotiate the extension from the moment the acquisition was made. We think he's going to solidify that position for us for at least the next three years."

– John Ferguson

Toronto traded 3 draft picks to acquire Toskala and Mark Bell from the San Jose Sharks, then signed their new goalie to an extension before he ever played a game in a Leafs jersey. The Andrew Raycroft experiment had failed, and they needed a new backstopper. The objective in acquiring Toskala was to replicate the success Calgary enjoyed when it plucked a back-up goalie from San Jose named Mikka Kiprusoff a few years earlier. Spoiler alert: Vesa would never win a Vezina trophy.
 
Vesa’s first season with Toronto was below average, but performed respectively relative to his cost (on the final year of his previous deal), but he got progressively worse the longer he was with the team. By the time this contract started, he was awful. In the final year Toskala had a 3.66 GAA and .874 SV% in 26 GP with the Leafs before being flipped to Anaheim in exchange for another bad contract (JS Giguere). The Ducks then traded him to Calgary, where he played 6 games, marking the end of his NHL career. He would play 24 games in Europe after this.
 
 
10. Tim Connolly
 

Signed By:	Brian Burke		Position:	F
Date:	2011-07-02		Age July 1st:	30
Term:	2 years		Playoff GP:	0
Total Money:	$9.5M		Playoff PTS:	0
Cap Hit:	$4.75M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.2	70	36	104
Per 82 GP	6.1	82	42	122	17.0

“This is the most excited I’ve been for a season in a long time”

– Tim Connolly

Tim Connolly was a player with elite offensive gifts who was never able to hit a free agency jackpot due to a reoccurring injury history. His first foray into UFA status only produced a 2-year deal due to the concerns about his durability, and the first year of that pact produced a career high 65 PTS in 2010. The center would get another crack at the UFA market one year later at age 30 after dropping to 42 PTS. Smartly the Leafs only gave him another 2-year deal, avoiding an even greater catastrophe than the one that blew up in their face. Burke had reportedly been pursuing Brad Richards, and only settled on Connolly after Richards signed with the Rangers (which you can read about on the Rangers worst contract list).
 
The first season in Toronto was statistically similar to his last in Buffalo, but saw a large drop in his power play time, which obviously hurt his scoring and shot production. He wasn’t a good fit with head coach Randy Carlyle, and by year two cleared waivers and was sent to play for the Marlies, where he scored 12 PTS in 28 GP. You could blame this disappointment on bad deployment, but no matter how you justify it, getting paid that much money to play in the AHL is a disaster. Brian Burke was fired before this agreement expired.
 
 
11. Luke Schenn
 

Signed By:	Brian Burke		Position:	D
Date:	2011-09-16		Age July 1st:	21
Term:	5 years		Playoff GP:	12
Total Money:	$18M		Playoff PTS:	3
Cap Hit:	$3.6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	22.3	335	75	383
Per 82 GP	4.5	82	18	94	17.6

"I'm looking forward to the next five years here in Toronto."

– Luke Schenn

Luke Schenn had the best season in the entirety of his career in the final year of his ELC, scoring 22 PTS averaging 22.4 minutes of ice time. This treaty did not get signed until the middle of September, at a slight overpayment for what that production should have been worth. The first season saw Schenn replicate his total of 22 PTS, but his ice time plummeted down to 16 minutes per game. Burke shrewdly chose to trade Schenn that summer, and achieved an impressive return plucking James Van Reimsdyk from the Flyers. JVR was on a very team friendly deal.
 
Hindsight being 20-20, we didn’t know at the time that Schenn was not any better than a 3rd pairing defenseman, who in these 5 seasons only surpassed 19 minutes of average ice time once. The good news for Toronto is that they shipped him out of town before it became too obvious that he was going to fall short of expectations. The Flyers bore the brunt of the badness, getting a decent player but compensating him at twice the rate he was earning. They were able to salvage a 3rd round pick by selling him as a rental in the final year.
 
 
12. Joffrey Lupul
 

Signed By:	Dave Nonis		Position:	F
Date:	2013-01-20		Age July 1st:	29
Term:	5 years		Playoff GP:	0
Total Money:	$26.3M		Playoff PTS:	0
Cap Hit:	$5.3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	30.8	170	79	390
Per 82 GP	6.2	82	38	188	16.5

"Haha failed physical? They cheat, everyone lets them. I'm ready. Just awaiting the call."

– Joffrey Lupul

The oft-injured Joffrey Lupul landed in Toronto as a throw in to the 2011 Beauchemin for Gardiner trade to help with Anaheim’s cap number and Joff found success early in his Toronto tenure. In 2012 he won the Masterson trophy after scoring a career high 67 PTS in 66 GP, which earned him this extension at the beginning of the lockout shortened 2013 season. He was injured again shortly afterwards, but still managed 18 PTS in 16 GP in limited action. Loops scored 103 PTS in his first 110 games with the Leafs (before this deal began) while playing predominately on a line with Bozak and Kessel.
 
Once this contact commenced, Lupul was moved off the Kessel line to play with Nazem Kadri, and his scoring rate dropped substantially. The diminishing scoring and reoccurring injuries continued over the next few seasons, until team doctors determined he was no longer fit to play hockey. There’s some debate over just how injured Lupul actually was, saying himself at one point that he was good to play while team doctors disagreed. There’s an argument to be made that this wouldn’t have been a bad deal had the injuries never happened, but they knew what they were buying. There was a long history of health issues before he arrived in Toronto, and he still only produced 38 PTS per 82 GP under this agreement for an adjusted cap hit of $6.1M.  He’s now living a very happy life post-retirement, enjoying all that money in his bank account.
 
 
13. Nikita Zaitsev
 

Signed By:	Lou Lamoriello		Position:	D
Date:	2017-05-02		Age July 1st:	25
Term:	7 years		Playoff GP:	14
Total Money:	$31.5M		Playoff PTS:	2
Cap Hit:	$4.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	32.3	316	67	324
Per 82 GP	4.6	82	17	84	21.2

"We felt that after having him here a year and certainly watching him over the last couple of years, everything we thought about him was what we saw. The way he plays, the style he plays, the way he takes care of himself, for a defenseman, we felt this was a good decision.”

– Lou Lamoriello

Nikita Zaitsev had a marvelous rookie season in Toronto with 36 PTS, averaging over 22 minutes of ice time per game. The Russian needed a new agreement when that first contract expired, and Lou Lamoriello paid him close to what you should pay a 30-point D-man. The problem was giving a 7-year term to a player with only a single season of NHL experience. In the first year of the new deal, Nikita played close to the same number of minutes per game, but his scoring rate dropped in half. The lightning he captured in a bottle early did not prove to be replicable.
 
Zaitsev and his new contract quickly drew the ire of Leaf nation, prompting the Leafs to trade him to Ottawa in a large multi-player exchange. Lou would not be around to execute that trade, as he was relieved of his command a year after this was signed. Zaitsev’s best skill at this stage of his career is eating minutes, though he’s not terribly effective with that opportunity.
 
 
14. John-Michael Liles
 

Signed By:	Brian Burke		Position:	D
Date:	2012-01-25		Age July 1st:	31
Term:	4 years		Playoff GP:	4
Total Money:	$15.5M		Playoff PTS:	0
Cap Hit:	$3.9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	19.1	211	63	304
Per 82 GP	4.8	82	24	118	19.6

"As far as money goes, you could say that you leave some on the table. Maybe I did, maybe I didn't ... but I'm looking at it as I was negotiating a contract to stay in a place I wanted to be and play on a team I wanted to play on and live in a city I wanted to live in.”

– John Liles

John Liles scored 46 PTS in 2010/11 with Colorado before he was traded to the Maple Leafs for a 2nd round pick. Burke locked him up with a 4-year extension in the middle of his first year in Toronto despite a drop in his offensive contribution. The salary he earned was still defensible given his stat line, but the risk factor was age and term. This started at age 31 and lasted 4-years, which is not as uncommon as you might think for defensemen of this age (unfortunately many of those names can also be found in this book). Darker days were yet to come.
 
The D-man had injury issues in year one of the deal, where his scoring rate dropped even further. By the 2nd year, Liles was waived and sent to the AHL. He would score more points for the Marlies than the Maple Leafs over this deal, before they moved him in a bad contract swap with the Hurricanes, acquiring Tim Gleason (who was out of the league one year later). Liles finished with the Bruins, who retained him on a 1-year deal for $2.2M, which would mark the end of his pro career.
 
 
15. Andrew Raycroft
 

Signed By:	Turd Ferguson		Position:	G
Date:	2006-07-04		Age July 1st:	26
Term:	3 years		Playoff Wins:	0
Total Money:	$6M		Playoff SV%:	0.000
Cap Hit:	$2M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	3.3	91	39	3.17	0.890

"He's a proven No. 1 goaltender, former rookie of the year. He's going to look great in our uniform"

–John Ferguson

The worst part of the Andrew Raycroft acquisition for Toronto wasn’t necessarily the contract he was awarded by Ferguson shortly after the trade but rather the fact that they traded away a young Tuukka Rask to get him. It did not work out as planned. Raycroft’s last season in Boston saw him put up a 3.71 GAA and .879 SV%, so there should have been red flags to discourage the Leafs from trading a blue-chip goaltending prospect they drafted in the 1st round a year earlier. Rask would go on to have an All-Star career for the Toronto Maple Leafs Boston Bruins and played a key roll in defeating the Boston Bruins Toronto Maple Leafs in multiple future playoff series…
 
Raycroft’s first season in Toronto was faulty, but he did manage to set a new franchise record for wins by a goalie, as the Leafs narrowly missed the playoffs. By year two, this investment was a full-blown shit show, earning only 2 wins with a 3.92 GAA and .876 SV%. Tuukka Rask also holds a Leafs record, career wins by a goalie drafted by Toronto, so congratulations! There were a few other contracts who nearly qualified for this list and might have led to a greater net loss, but Andrew earned this spot because of the opportunity cost of losing Tuukka.