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    Nick Barden
    Nick Barden
    Sep 10, 2025, 16:07
    Updated at: Sep 10, 2025, 16:07

    Kawhi Leonard reportedly wanted a stake in the Toronto Maple Leafs to remain with the Toronto Raptors in 2019.

    After joining the Raptors in a mid-summer trade in 2018, Leonard helped guide the city to their first-ever NBA title. Following the historic championship run, Leonard was a free agent, with several teams inquiring about his services.

    According to Toronto Star columnist Bruce Arthur, Leonard’s uncle and representative, Dennis Robertson, made several demands to the Raptors during the free agency period in hopes of remaining in Toronto. 

    One of the reported asks on the list was to become a part-owner of the Maple Leafs.

    “According to those sources, who were granted anonymity in order to speak freely about the negotiations, Robertson’s list was long and absurd,” Arthur wrote. “It included a trade for (Paul) George, which featured an exorbitant price tag. It included a slice of ownership of the Toronto Maple Leafs, which Robertson was told was impossible.”

    Leonard ended up not signing with the Raptors and instead returned to his home state of California, where he inked a three-year, $103 million contract with the Los Angeles Clippers. Since then, the 34-year-old has signed two more deals with the Clippers worth a combined $325 million.

    At the time of Leonard’s ask, MLSE (Maple Leaf Sports and Entertainment) was owned by Bell, Rogers, and Kilmer Sports. This summer, however, Rogers closed a deal to purchase all of Bell’s shares, giving Rogers a majority 75-percent stake in MLSE.

    The other 25 percent is owned by Kilmer Sports (Larry Tanenbaum). However, according to Yahoo Sports, “Edward Rogers and Tony Staffieri both expect that the company will exercise its 2026 option to purchase the remaining 25% of MLSE owned by Larry Tanenbaum via his Kilmer Sports Ventures.”

    What that means for the Maple Leafs is yet to be seen. Nonetheless, this offers a peak behind the curtain of the business side at MLSE, from the time Leonard was a free agent in 2019 to the present, with Rogers holding a majority stake in the company plus full ownership of the Toronto Blue Jays.

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