Punishment for Steve Ballmer Reportedly Being Discussed as Kawhi Leonard Investigation Drags On

The Kawhi Leonard trade is stalled, not by facts, but by a negotiation over punishment. Technically, Leonard is still a member of the Los Angeles Clippers. He was traded earlier this offseason to the Toronto Raptors, but the move back to Canada has been put on hold until the league completes its investigation into the Aspiration case involving Leonard and the Clippers.

NBA Commissioner Adam Silver has said he wants the issue resolved before the 2026‑27 season begins. But according to Substack analyst Vivek Jacob of “Raptors in 7,” the real holdup is deciding on a punishment for Clippers owner Steve Ballmer, one Silver believes Ballmer will accept.

Jacob noted that Ballmer is the richest owner in the league, and Silver will want to “maintain that relationship.” For observers, it may seem absurd that an offender gets to influence the extent of his punishment, but that dynamic is reportedly at play.

Aside from Leonard, two other players are affected by this investigation. Brandon Ingram and Gradey Dick, the players whom the Raptors sent in exchange for Leonard, remain in Toronto.

If the 2026-27 season begins without the NBA reaching a conclusion, Ingram and Dick will be in an awkward situation.

In a report by Michael Grange on Sportnet in mid-July, Ingram and Dick have been told to look for a place to live in Los Angeles. This means there is an assumption that the deal will still push through.

Since the deal has not officially gone through yet and they are still members of the Raptors, it raises the question of what will happen at the start of the season if the investigation has not concluded.

The Kawhi Leonard Investigation Could Extend To 2027

Adam Silver and the teams involved in the trade will definitely want the NBA's probe to finish before next season begins. However, there is no assurance that this will be the case. In fact, there is a belief that it could take much longer and will extend into next year.

In a recent article by Baxter Holmes for ESPN, he said the whole saga could extend into the next calendar year. This would be the case if those involved are unable to reach an agreement on specific matters.

One is the facts of the case, and the other is the appropriate punishments.

The NBA has shown patience regarding the case. They have not made any statements or provided any updates on it, nor have they decided on any appropriate sanctions.