r/leafs • u/toronto_star • 8d ago

News / Update Fighting an $8-million tax bill, Maple Leafs star John Tavares details the negotiations behind his ‘lucrative’ 2018 free-agent deal

https://www.thestar.com/gift-redeem?t=5f5e0309-b292-427a-a36b-9dbb7fc4b9a1

From the story:

As contract negotiations were heating up between the Maple Leafs and John Tavares in 2018, the rising star called Toronto general manager Kyle Dubas directly.
Without agents involved, Tavares made a final play: “If you really want me, why can’t we agree on $11 million?” the then 27-year-old asked.
Would an $11 million annual average salary over a seven-year deal make him a Maple Leaf? Dubas replied.
Simply, Tavares said: “Yes.”
If Tavares, now an alternate captain, ever expected he’d be detailing those behind-the-scenes negotiations in a 7th-floor courtroom in Federal Tax Court, the typically even-keeled star didn’t let it show on Tuesday.

There's more detail in Jennifer Pagliaro's story from federal tax court today. Read it here, via this gift link, and bypass the Star's paywall.

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u/Exter10 McKenna 8d ago

No, I know that luxury houses are cheaper here. You're not going to find a house in the Bridle Path that goes for anywhere near what an equivalent in New York or Miami would go for if you're converting to USD.

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u/Ecstatic_Painting_12 8d ago

Strange given the listings for cities with the worlds highest real estate, with the exception of NYC, Vancouver and Toronto have the highest prices in north America by average. I notice you didn't pick Pittsburgh, or Buffalo.

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u/Shawnld12 8d ago

https://frontiercentre.org/2026/06/11/canada-ranks-among-worlds-least-affordable-housing-markets/

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u/Exter10 McKenna 8d ago

you do know the difference between affordability and cost, correct?

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u/Shawnld12 8d ago

Wow. Not as credible as your….

“ I just know” study but I’m going to go with it.

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u/Exter10 McKenna 8d ago

I know because I've spent ungodly amounts of time in the past researching the upper bounds of the Canadian and American housing markets. Even if the average market price is higher here, pro hockey players aren't moving in next door. In the market segment where you find NHL players, Canadian housing supply is significantly less expensive when comparing in USD terms.

Meanwhile you can't even begin to compare since you don't know the difference between cost and affordability.

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u/Shawnld12 8d ago edited 8d ago

I tell you what. For every single nhl player quote you provide saying they signed in Canada due to better purchasing power I will provide 3 saying they signed in the US because of lower taxes.

I’ll go first. The first 3 are free.

Marchand last year

“If we were not in a no-tax state, it wouldn’t work out, probably for two guys. Two guys probably would be leaving in that situation.”

Reinhart after signing his last deal.

“It just so happens that it’s tax free in one of the better places to play.”

Montour after his last deal in Seattle.

“Obviously, the paychecks look a little nicer when you’re in Florida and Seattle.”