Clippers' concessions to superstar may have cost Raptors a dynasty

The Raptors won their first NBA title in 2019 after a risky trade for Leonard propelled them the the Finals. They dealt franchise icon DeMar DeRozan and center Jakob Poeltl to the San Antonio Spurs for Leonard, who requested a trade after disagreeing with the Spurs about how to manage his injuries, according to a report from ESPN's Baxter Holmes.

But when Leonard hit free agency, he and his uncle, Dennis Robertson, reportedly made outlandish demands, like houses, private planes and ownership stakes in interested teams. He asked the Raptors for stakes in other companies held by team ownership and at least $10M in endorsement deals for which he "didn’t want to do anything." Team sources say the Clippers acceded to at least some of these demands.

Toronto would have been a perennial contender with Leonard

Had Leonard stayed, or perhaps the Raptors been more willing to bend the salary cap rules, the Raptors were well positioned to make sustained run of contention. They had a former Defensive Player of the Year at center in Marc Gasol, an All-Star guard in Kyle Lowry and future All-Stars in Fred VanVleet and Pascal Siakam. On the bench, they had emerging defensive ace OG Anunoby and scorer Norman Powell.

Not only was Leonard a good fit from a basketball sense, playing in Toronto gave him the relative privacy he wanted outside of a major American market. The Raptors also tolerated his absences without complaint, allowing him to play just 60 of their 82 games in his lone season there.

The Raptors were good enough to go 53-19 the next season after losing Leonard for nothing, even better than their 58-24 record in 2018-19. With Leonard, they would have likely been the title favorites in 2020 — especially if Danny Green had stayed in Canada rather than jumping to the Los Angeles Lakers.

Leonard may have gotten the perks and no-effort endorsement deals he wanted in Los Angeles. But he might have missed out of his best chance at more titles by leaving Toronto.