Historical Best
Contracts Lists
2022: Winner: Cale Makar, runner-up: Jack Hughes
2021: Winner: Nathan MacKinnon, runner-up: Leon Draisaitl
2020: Winner: Nathan MacKinnon, runner-up: Leon Draisaitl
2019: Winner: Nathan MacKinnon, runner-up: Alksander Barkov
2018: Winner: Nathan MacKinnon, runner-up: Seth Jones
2017: Winner: Nikita Kucherov, runner-up: Roman Josi
2016: Winner: Nikita Kucherov, runner-up: Tyler Seguin
2015: Winner: Tyler Seguin, runner-up: John Tavares
2014: Winner: John Tavares, runner-up: Victor Hedman
2013: Winner: John Tavares, runner-up: David Backes
2012: Winner: Claude Giroux, runner-up: Kris Letang
2011: Winner: Corey Perry, runner-up: Ryan Kesler
2010: Winner: Mike Green, runner-up: Corey Perry
2009: Winner: Ryan Getzlaf, runner-up: Shea Weber
2008: Winner: Henrik Zetterberg, runner-up: Sedin Twins
2007: Winner: Miika Kiprusoff, runner-up: Danny Heatley
2006: Winner: Miika Kiprusoff, runner-up: Henrik Zetterberg
By definition some of these deals aren't precisely bargains in the true sense of the world (it can be hard to say that the highest paid player in the world is playing for a discount). Some of these players were disqualified from my annual "best bargain" list in past years because they made too much money, but not here. Here we are emphasizing the word "BEST".
Enjoy!
"He came back after he talked to Pat and said this AAV
is really what I want to help the team. He's never been reluctant to help the
team and we certainly appreciate that. It says a lot about Crosby."
How much is Sidney Crosby worth? Whatever he wants to get paid. If he demanded the maximum 20% of the salary cap, somebody would give it to him. Whether he’s RFA or UFA doesn’t really matter, if the best player in the game ever made it to July 1st, somebody is drafting that offer sheet. Sid was scheduled to become UFA at the end of his previous deal, but he never made it close to the open market.
He didn’t ask to become the league’s highest paid player, he didn’t even ask for a higher cap hit than his rival Alex Ovechkin. Instead they cleverly crafted a 12-year back-diving deal that would pay him a whole bunch of money up front, circumventing the salary cap, then dropping down to $3M salary the final 3 years (while his cap hit was lower than Ovie, Crosby’s actual salary was significantly higher). This type of contract was soon going to become illegal, but in the meantime, it allowed the Penguins to give Sid a bunch of money up front to lower his annual cap hit.
Some pundits were critical of the deal given Sid’s recent concussion issues, but that dissention would soon fade into oblivion, as Crosby quickly re-established himself as the game’s best player, winning the Hart trophy in 2014. The first 6 years produced 4 Hart nominations, 2 Stanley Cups, 2 playoff MVPs, and over 500 PTS. With what has been accomplished, it really doesn’t matter what happens on the back end of this contract because the team has already received the best possible value attainable.
The Cap Recapture penalty won’t be an issue. If Sid so much as gets a headache in 2022, they can put him on LTIR. Anytime you can get the best player in the world for less than the league maximum, you’re doing great.
"Building a team to win the Stanley Cup was a constant point of
discussion."
It’s hard to put a price on players this good, one of the league’s best talents, with very few peers worthy of direct comparison. $100M is a good place to start. The simple answer is to say that McDavid is worth the maximum amount you’re allowed to pay a player under the CBA, despite the fact that no player has ever made 20% of a team’s cap since the salary limit was introduced. Sidney Crosby took a discount (as a % of the cap), but also got a 12-year back-diving contract that has since been made illegal.
Chiarelli claimed he had offered Connor a higher salary on shorter term, but that McDavid decided to stretch it to 8 years to lower the cap hit and help the team build a champion around him. Oilers fans can say what they want about Peter Chiarelli, but his signature has been on a few magnificent contracts.
It’s a safe bet that Connor will be in the MVP conversation for the duration of this deal, and if the cap continues to grow, it will only become a greater bargain. They bought 4 years of unrestricted free agency from one of the game’s best players. What we do in life, echoes in eternity. Some called this a “hometown discount” when it made him the highest paid player in the league, and they might be right.
"That's the
dumbest thing I've ever heard. You will regret this decision for the rest of
your life!"
-NBA Commissioner David Stern (to Ted Leonsis)
Alex Ovechkin scored 163 regular season goals over his entry level contract, by far the most since the standard ELC was invented in 2005 (Laine scored 110). This contract made Ovie the highest paid player in the NHL, so it’s hard to call this a bargain, at least in the early years. Alex is arguably the greatest natural goal scorer in NHL history and could have written himself a blank cheque had he ever tested free agency (and may very well if he goes UFA in 2021 at age 35).
Over the first 12 years, Ovie led the NHL in goals scored 7 times (543 total goals), won the Hart trophy twice, won a Stanley Cup and a Conn Smythe as playoff MVP. He’ll be a first ballot Hall of Fame player. It should be noted that there was a blip during the Dale Hunter administration when this contract got a failing grade. Dale tried to force Ovechkin to make a greater commitment to defense, leading to his worst statistical season with 65 PTS. Nicklas Backstrom also missed half that season due to injury. I overreacted and put Ovie on my 2012 worst NHL contracts list, which in retrospect, might be my all-time worst premature declaration of badness.
There was another downturn near his 30th birthday when it looked like all those years of heavy hitting and hard partying might have finally caught up with him, scoring 33 goals and 69 PTS in 2017. That too proved to be short-lived, as he won another Maurice Richard trophy in 2018. As the salary cap has gone up, the AAV has become more reasonable. It’s hard to say that a guy who got paid $124M left money on the table, but absolutely Ovie could have made more money than this had he taken the Crosby route, accepting less term to attain UFA status sooner. Not that it matters. He has more money than he’ll ever spend. Maybe Alex’s great grand children will complain that he didn’t maximize career earnings.
"I was just excited to get paid that much money at such a young
age."
Nathan MacKinnon wants you to know that he doesn’t care that his contract is a ridiculously low-priced mega-bargain, and claims he’ll take another discount on his next deal. Too bad the Avalanche don’t re-invest their savings and spend to the cap. On the open market, MacKinnon could get whatever price he wants, even a max deal, as most consider him to be among the five best players in the NHL. It’s ironic to say that a kid who banked $44M is critically underpaid. He should be able to get off food stamps when he signs his next deal.
MacKinnon came within an inch of winning the Hart Trophy in 2018 and will be a perennial contender for the foreseeable future. Nate was actually slightly over-paid in year one, then was shot out of a cannon in year two. It doesn’t matter who you put on his line, he’s a machine. Nate also made Mikko Rantanen a rich man.
Fun fact: MacKinnon signed for the exact same year one adjusted cap hit as fellow first overall pick John Tavares received on a 6-year deal in 2011. That may not be a coincidence. Ryan Nugent-Hopkins also received a comparatively similar deal 3 years earlier. There was a historical precedence for this structure.
“It’s seven years.
It’s a big commitment on their side and I’m very pleased they were able to do
that. It really shows they believe in what I do and they want me to a big part
of this organization.”
Erik Karlsson signed this contract the day before he won his first Norris Trophy in 2012. It’s possible that he could have squeezed out a few extra dollars after the win, but the league was also facing a potential lockout, so there was likely some urgency to get a deal done before new salary restrictions were possibly introduced. This was a slightly cheaper version of the Drew Doughty deal from a few months earlier.
The contract would get off to an auspicious start after Matt Cooke intentionally sliced Karlsson’s achillies with his skate, costing him most of the shortened season. The Swede would return to form and win another Norris trophy in 2015, also carrying the Senators on his shoulders to the Conference final in 2017. Rather than lose him for nothing when the contract was over, Ottawa traded him to San Jose for a package of players, prospects, and picks. The Sharks gave Erik $92M.
"At the end of
the day, until it's signed, some people will think there's a possibility I
don't want to be here. I don't quite understand it; I never have.”
John Tavares signed this extension 9 months before the expiration of his ELC, after scoring 67 PTS in 79 GP. Waiting until the end of the season would have undoubtedly raised his price point, having scored 81 PTS in 82 GP. Clearly it was a massive mistake for him to lock in for 6 years at the price you’d pay to a 60-point center. This was the first overall pick a few years earlier who had been branded as a generational talent.
Of all the people to bet on themselves, Johnny should have been one of them. He deserved something in the range of Backstrom or Stamkos. Yet this set the template for Victor Hedman to sign a similarly low-ball offer from Tampa, and Nathan MacKinnon a few years later, all three of which are among the best bargains of the last 15 years.
Year one of this pact produced a Hart trophy nomination for league MVP, as did year three. He scored 419 PTS in is 426 GP (at a rate of 81 PTS per 82 GP), all this despite suffering a major knee injury at the 2014 Olympics.
“Roman has proven,
with his growth and success here in Nashville and on the international stage,
that he is one of the best young defensemen in the NHL. Roman’s skating ability
and instincts have allowed him to play in all key situations. With today’s
signing, we have our top defensive pairing locked up long-term, and we look
forward to Roman’s continued development and contribution to the Predators’
on-ice success.”
Roman Josi still had not broken out as an offensive weapon when Poile decided to offer him a 7-year extension. The Swiss defenseman had only played 100 games in the NHL but was already logging heavy minutes in his sophomore campaign. Whether or not Poile foresaw the potential scoring ceiling, it was at the very least clear that Josi was a gifted player.
The ascent happened fast. His points per game almost doubled from the last year of his entry level to the 2nd year of this contract. By year two he scored 55 PTS and averaged 26.5 minutes of ice time. One person who certainly failed to forecast that future apex was Josi’s agent, who sold his client short on a 7-year term that would not expire until Roman was 30-years-old.
This had the potential to backfire in a Mattias Ekholm sort of way, but luckily for Josi, he became so incredibly good that the Predators still paid him $72M at that age. He left some money on the table in the front end, but he might reclaim it on the back end depending how he ages. Currently he shows no sign of slowing down, enjoying the best year of his career at age 29.
"For me, it was
never a question of going anywhere else or signing anywhere else. That never
even crossed my mind. I wanted to stay in Edmonton, I feel very comfortable
there. I think we have a great group of guys and we're building something
special."
When Leon Draisaitl signed this 8-year extension in 2017, it seemed like a substantial overpayment based on comparables. Elite young centers like Barkov, Scheifele, and MacKinnon were getting paid much less, so there was some logical sense to the conclusion that Leon should have received a smaller sum. It was nominally the exact same salary that Steven Stamkos received as an unrestricted free agent one year earlier.
But it was perhaps Evgeny Kuznetsov who first shifted the market for young RFA centers 6 weeks earlier, followed by Ryan Johansen, then Leon. Draisaitl had a scoring regression in year one, only strengthening the argument of anyone saying he was overpaid. That all changed in year two when he became one of the league’s top scorers, playing over 22 minutes per night, topping 100 PTS.
Any debate about whether or not he’s a bargain has been settled. Anyone who wanted to argue that his production explosion should be credited to playing with Connor McDavid, inflating his numbers beyond what he should be capable of producing, lost the argument in year three when Leon was moved off McDavid’s line and continued to score at an elite level. Draisaitl is the real deal and has become drastically underpaid, winning the Hart trophy in 2020.
“He is one of the
hardest working guys on our team and other guys follow that, they look up to
that. We're blessed to have him on our team."
If you’re wondering how Ken Holland was able to convince Henrik Zetterberg to accept such a team friendly deal, the young Swede had topped out at only 44 PTS over his first 2 seasons. Henrik would return from Sweden in August 2005 as a completely different player, scoring 39 goals and 85 PTS amid the obstruction crackdown.
This is among the most incredible bargains of the salary cap era, even accounting for cap inflation. The Red Wings received 292 GP, 318 PTS (89-point pace), 1167 shots, +98, 125 power play PTS, 2059 face off wins, and that’s just regular season. He also won a Stanley Cup and a playoff MVP. He would total 71 PTS in 69 playoff GP. This was like getting a $10M player for $4.6M.
“Individual honours
and scoring championships are great, but my No. 1 goal is to win the Stanley
Cup.”
Sidney Crosby won his first Hart trophy in 2007 as a sophomore, and had already established himself as one of the league’s best players when his ELC expired. Instead of asking for longer term, the two sides would agree on a 5-year deal with the potential to make him an unrestricted free agent at age 25.
Sid didn’t win any Hart trophies on this contract, but he was nominated twice and the Penguins won the Stanley Cup in year one. On a per game basis, these were the most productive years of his career, scoring 371 PTS in 257 GP, which translates to 118 PTS per 82 GP. Crosby was on pace to score 132 PTS in 2011 before a concussion at the Winter Classic ended his season. The injury would spill over into the following her, costing him most of the 2011/12 campaign. Anyone who doubted how effective he’d be upon his return were soon silenced when he scored 37 PTS in 22 GP.
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