“Show Me the Money” - the (2019) Auston Matthews Contract
The kwan – “… it means love, respect, community… and the dollars, too. The package.” Judd Moldaver must have been channelling his inner Jerry Maguire when the ink dried on Auston Matthew’s new five-year, $58.17 million contract on February 5, 2019 - and the hockey world took notice.
Not only had the young superstar secured the second-highest cap hit in the NHL at the time (trailing only Connor McDavid), but the structure and strategy behind his deal signaled a turning point in how elite players (and savvy agents) approach contract negotiations in a salary-capped league.
This wasn’t just a big contract - it was a blueprint.
Let’s take a moment to appreciate the brilliance of the precedent-setting 2019 Auston Matthews contract.
A Brief History
“You had me at ‘Hello’” - The Generational Player
Simply put, Auston Matthews was the “Frank ‘Cush’ Cushman” of the 2016 NHL Entry Draft.
He had broken the United States National Development Program record for most points in a single season, with 117, breaking the existing record held by then-NHL superstar, Patrick Kane, prior to playing out his draft year in the Swiss-A league, where he dominated. In a final showcase amongst his peers, Auston thrived in the 2016 World Junior Championship, finishing the tournament amongst the top scorers and being named to the tournament All-Star Team.
Patrik Laine made a late push to steal the pole position in the draft, with a strong performance at the World Championships, but many still pegged Auston Matthews as the clear-cut number one selection, if for no other reason than the fact that he could fill the coveted role of a number one centre.
It just so happens that the Toronto Maple Leafs had such a vacancy.
“It’s not ‘Show Friends,’ it’s ‘Show Business’”– Lou Lamoriello
When Auston Matthews was drafted first overall in 2016, it was expected he’d sign a “maxed-out” entry-level contract — $925,000 in salary, maximum signing bonus, and up to $2.85 million in performance bonuses. But one man stood in the way of this seemingly inevitable outcome: Lou Lamoriello.
The then–Maple Leafs GM was famous for his no-nonsense negotiation style and long-standing aversion to performance bonuses. In New Jersey, Lamoriello had refused to offer them even to top draft picks, believing young players should earn everything through team-first play, not individual incentives.
So, it raised eyebrows (and upset Mitch Marner) when Matthews, just weeks after being drafted, signed a contract that included every possible bonus available under the CBA. Under the guidance of agent Pat Brisson, Matthews secured a deal with full salary, full signing bonus, and performance bonuses that could net him up to $2.85 million per year.
“You are my ambassador of Kwan”– Judd Moldaver
In the summer of 2018, as the Toronto Maple Leafs ushered in a new era under GM Kyle Dubas, Auston Matthews made a pivotal move of his own — he switched agents, signing with Judd Moldaver of the Orr Hockey Group. The timing raised eyebrows. Matthews was approaching a major contract negotiation, and Moldaver’s client roster wasn’t as star-studded as his predecessor, Pat Brisson’s.
Moldaver, who partnered with Jeff Jackson (the architect of Connor McDavid’s $100 million deal), quickly proved he was more than up for the job. He understood Matthews' rising market power and helped frame the negotiation around that leverage, despite the CBA’s limitations for young restricted free agents.
At just 21, Matthews had already outpaced John Tavares in goals over the previous two seasons and carried the status of a franchise cornerstone. But because he was still on his entry-level deal, he lacked arbitration rights and very few (if any) teams would be able to stomach forfeiting four first round picks to offer Auston a contract with compensation exceeding $8.4 million per year. As a result, Matthews had very little leverage within the confines of the CBA.
Moldaver’s challenge was clear: negotiate from a position of strength even when the rules said otherwise.
“You Complete Me” – The Contract
The 5-year, $58.17 million deal maximized Matthews' earnings, minimized tax exposure, and positioned him to hit unrestricted free agency at his physical and market peak.
While other stars, like Connor McDavid, opted for the maximum eight-year term, Matthews took a shorter five-year deal that would walk him directly to unrestricted free agency at age 26 — right in his prime. With the NHL’s salary cap projected to rise over the next few seasons thanks to new U.S. TV rights deals and franchise expansions, Matthews positioned himself perfectly to capitalize on what could be a massive jump in player earnings.
But the brilliance didn’t stop there.
Matthews’ contract was front-loaded and bonus-heavy, with 96% of his compensation paid as signing bonuses rather than base salary. These bonuses — paid every July 1st — offered several key advantages:
Time value of money: Auston received and could invest large portions of his earnings immediately, accelerating his wealth accumulation.
Lockout and buyout protection: Bonuses are paid even if the league were to shut down or the team tried to buyout the contract.
Tax efficiency: Structuring payments as signing bonuses opened the door for more favourable cross-border tax treatment.
It was a masterclass in long-term leverage: Matthews secured elite compensation now, shielded his income from risk, and set himself up to cash in again when the cap (and his prime years) peaked.
“Who had I become? Just another shark in a suit?”– Taxes
“I went to Arizona State, I’m from Arizona, I break Arizona records, I’m a Sun Devil, man!” – Residency
Although Matthews played for a Canadian team, he was a U.S. citizen who spent most of the year in Arizona. That matters — because Canada taxes income based on residency. The Income Tax Act deems someone to be a Canadian resident if they spend 183+ days in the country per year. Matthews, thanks to a travel-heavy NHL schedule and an offseason home in the U.S., didn’t meet that threshold.
By ensuring that his “centre of vital interests” (like his home, driver's license, and social ties) remained in the U.S., Matthews managed to avoid subjecting the entirety of his salary to Ontario’s then-top marginal tax rate of 46.16%.
Instead, only income earned while Matthews was physically in Canada (roughly 73%) would be subject to Canadian tax. The remaining salary would be subject to the various jock taxes imposed by U.S. cities and states that he played in. It’s important to note, however, that these jock taxes are typically much lower than taxes imposed north of the border.
“First class is what’s wrong. It used to be a better meal. Now it’s a better life.” – the Signing Bonus
Here’s the real brilliance: Matthews’ contract was 96% signing bonus.
Thanks to a Canada–U.S. tax treaty, international athletes can only pay Canadian taxes to a maximum amount of 15% of the total signing bonus, with the remainder being taxed at the rate of the athlete’s resident state.
For context, in 2019, Ontario’s marginal tax rate was 46.16%, whereas the marginal tax rate for Arizona was 41.5%. That meant that Matthews paid far less tax on the majority of his contract than he would have if it were standard salary.
The result? Matthews saved nearly $785,000 per year in taxes compared to a Canadian resident with the same contract. Over five years, he accrued up to $3.925 million in savings — money he could invest, save, or otherwise enjoy.
Conclusion
Auston Matthews asked Judd Moldaver to “show him the money” and he delivered. Not only did Moldaver ensure that Matthews attained the second highest salary cap hit in the league, but he limited his client’s commitment to the Toronto Maple Leafs to five years – lining up an even bigger payday down the road, when Auston was at his physical peak.
Thanks to smart legal structuring, residency planning, and the strategic use of signing bonuses, Auston Matthews’ contract is a textbook example of tax-efficient athlete compensation. He stays compliant, reduces liability, and retains more of his earnings — all without crossing legal lines.
Judd Moldaver delivered the whole package – the dollars, the community, the love, and the respect. And Auston Matthews – well, he got the “kwan.”
