The Real Reason the Raptors’ Trade for Kawhi Leonard May Not Go Through

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Back in June, the Toronto Raptors agreed to send Brandon Ingram, Gradey Dick, two first-round picks, a first-round swap and second-rounders to the Los Angeles Clippers for Kawhi Leonard. The deal was earthshattering for a number of reasons, not the least of which is it reunites the two-time Finals MVP with the team he left in 2019.

Months later, however, the trade has yet to officially go through. The Raptors put it on hold until the NBA’s investigation into the Clippers’ alleged salary-cap circumvention in their Kawhi dealings was finished. Well, that investigation has officially concluded. The fines were historic. Leonard has offered an apology and expressed excitement for a fresh start in Toronto.

Yet, even now, with training camp just around the horizon, the trade has yet to go through. And frankly, everyone’s freaking out. The Raptors were initially billed as a threat to win the Eastern Conference after acquiring Leonard by many top Canada betting sites, as MyTopSportsbooks.com has pointed out. At the moment, though, some places have pulled Raptors futures altogether. Others are treating it as if the trade will go through. But truth be told, nobody really knows what will happen.

This is unprecedented territory. Major trades have been held up before. Usually, however, it is because of physicals. Or because teams need to complete other business first. In this case, the reason for the delay and potential scuttling of the deal isn’t something different. And it is not what you think.

The Clippers May Be Dragging Their Feet to Spite Kawhi Leonard

Everyone’s first inclination here will be that the investigation has forced the trade into this holding pattern. That is partially true.

The Clippers were docked five first-round picks and fined $30 million by the NBA. Suspensions were also handed out to owner Steve Ballmer (one year), president of business operations Gillian Zucker (one year) and lead basketball executive Lawrence Frank (six months). As many league insiders continue to point out, the Clippers are still trying to figure out who’s running basketball operations following the spate of suspensions. Though the odds-on favorite is assistant general manager Trent Redden, this decision is a process.

Still, this isn’t what’s threatening to derail the deal entirely. The real reason? It might be hurt feelings.

According to Marc Stein of The Stein Line, people around the league believe the Clippers are furious that Kawhi accepted the NBA’s punishment (a $700,000 fine on his part) and offered an apology. By doing so, he ensured the NBA Players’ Association would not take the case to an arbitrator. As it turns out, that is the only way this case could go to arbitration. In turn, this means the Clippers do not have any clear recourse to appeal commissioner Adam Silver’s ruling unless they sue the league in the court.

Like Stein and others report, Los Angeles is apparently weighing that possibility. In the meantime, the Clippers are holding up Leonard’s ability to join his new team—not to mention keeping the Raptors in lurch.

What Are the Chances This Trade Collapses?

The fact that there is even a non-zero chance the Raptors’ trade for Kawhi ends up imploding is harrowing for the entire organization. This wasn’t just Toronto’s biggest move of the offseason; it was a landscape-altering deal for the entire NBA.

In the event that the Clippers submarine the trade to get back at Leonard or as part of their potential litigation process, it erases an Eastern Conference contender from existence. The Raptors were good last season. They were not great. And they have virtually no path to exploring greatness by just running it back with Brandon Ingram and Gradey Dick.

This says nothing of the organizational awkwardness. Welcoming back Ingram and Dick after just trying to trade them could create all sorts of tension. The Raptors might make far less splashy follow-up deals just to avoid the choppy waters altogether.

With all of that said, if we had to guess, Toronto’s acquisition of Leonard will invariably get finalized.

As much as the Clippers might want to fight back against the NBA’s ruling, they have almost no legal ground on which to stand. Their refutes of the allegations have never once harped on the merits of what was found. If they take this to court, they open themselves up to an even more extensive discovery process. Given what the NBA’s white-shoe law firm discovered in its investigation, this would put the Clippers in an incredibly vulnerable position.

Plus, if they are destined to lose, they need every first-round pick they can get. The Raptors are sending them two first-rounders outright. This is a deal that helps ensure the Clippers will not be completely barren of draft picks after losing first first-rounders, beginning in 2029.

All of which comes as good news to the Raptors, and to their fans. But any and all optimism must be couched with caution. This agreed-upon deal has already traveled down rabbit holes galore. No one involved should believe it’s done until it’s actually official. And the longer it remains unconsummated, the more likely it is that the Raptors’ 2026-27 ambitions blow up in their face.