Kawhi Leonard could sign one of the biggest contracts in NBA history if he takes a bold gamble to stay with the Raptors short-term

If Leonard stays with the Raptors on a two-year deal, he would have 10 years of experience when he hits free agency in 2021. NBA players with 10 years of experience can sign max contracts worth 35% of the cap, and the salary cap will be higher in 2021.
Such a deal would also be a risk for Leonard, as Kevin Durant and Klay Thompson just suffered major injuries in the Finals on the eve of free agency.
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Kawhi Leonard could benefit big time by dipping his toes back into free agency in 2021.

Leonard's 2018-19 season felt like one big build-up to free agency. All season long, rumors persisted about where he would land in the offseason, with the Toronto Raptors doing all they could to convince him to re-sign while other teams, like the Los Angeles Clippers, made overtures to lure him away from Toronto.

However, as noted by ESPN's Brian Windhorst, Leonard could re-sign with the Raptors on a two-year deal that would set him up to sign one of the biggest contracts in NBA history.

This summer, Leonard could sign a five-year, $190 million contract with the Raptors, or a four-year, $140 million contract with another team.

Windhorst wrote that another option for Leonard would be to sign the notorious "1+1" contract a two-year deal, with a player option in the second year for $33 million in the first year, then $36 million in the second.

Such a deal would allow Leonard to hit free agency again in 2021 when he has 10 years of experience in the league. Free agents with 10 years or more experience can sign a max contract worth 35% of the salary cap.

Salary cap projections for the 2021-22 season are hazy. It was recently projected at $116 million for the 2020-21 season, while Spotrac lists the 2021-22 cap at $121 million. If we were to assume the cap lands at $118 million in 2021-22 (the NBA did not immediately respond to an email about the cap projection for 2021-22), Leonard could re-sign with the Raptors for five years, $239 million or join another team for four years, $177 million.

According to Spotrac , in total cash, those deals would rank as the biggest or third-biggest in NBA history, respectively. Of course, in the next two summers, there will be contracts signed that will change that list. Regardless, Leonard can become one of the highest-paid players of all-time.

Windhorst said on ESPN's "Get Up!" on Thursday that he thinks Leonard will pursue a two-year deal with the Raptors.

Such a contract would come with some on-court benefits, too. The Raptors are champions, and re-signing short-term would allow Leonard and the Raptors to run it back in a season that is shaping up to be wide open. The Raptors have several players whose contracts expire in 2020. The Raptors could keep the team together for one or two years to try to remain atop the NBA.

kawhi leonard kevin durant Vaughn Ridley/Getty Images

Furthermore, Leonard will be 30 years old in 2021. It's possible that a team would balk at paying Leonard an average of $47 million or $44 million per year as he enters his 30s. Age didn't affect max contract offers for LeBron James, who was 33 when he signed with the Los Angeles Lakers, and it doesn't appear that it will affect Durant's free agency (he's 31). But Leonard has also played deep into the postseason for most of his career and would presumably continue to if he stayed with the Raptors.

It may not matter in the end, but it would have to be a consideration for Leonard and his team this summer.

Leonard has remained tight-lipped about his decision in free agency. Nobody would blame Leonard for cashing-in this summer, either by re-signing with the Raptors long-term or moving closer to home by joining the Clippers.

But if Leonard wants to remain with Toronto for just a little while longer while setting himself up for a massive payday down the line, he could get creative with his next contract.