New criminal investigation adds hurdle for Raptors in delayed Kawhi Leonard trade

Even though the NBA has run its course with its investigation into salary-cap circumvention involving Kawhi Leonard and the Los Angeles Clippers, it feels like the situation is far from over.

And the Toronto Raptors seem to be the unfortunate recipients of the collateral damage, despite not even being involved in the case in the first place.

On Thursday, The New York Times reported that the U.S. Department of Justice has opened an investigation into allegations that the Los Angeles Clippers helped arrange secret sponsorship contracts for star player Kawhi Leonard that circumvented the salary cap.

Last week, the NBA ruled that it had found a pattern of misconduct and multiple significant rules violations by the Clippers organization, while Leonard had "no knowledge" that his uncle and business manager, Dennis Robertson, assisted him in obtaining off-court income opportunities.

NEW and BREAKING: Justice Department prosecutors have opened a criminal investigation into revelations the Clippers helped arrange secret sponsorship contracts for the star player Kawhi Leonard that circumvented the salary cap. https://t.co/0CLwBwTfdk
w/@WRashbaum @SantulN

— Michael S. Schmidt (@nytmike) September 10, 2026

The NBA handed Clippers owner Steve Ballmer a $30-million fine, in addition to a one-year suspension from all league activity. Los Angeles was also stripped of five first-round draft picks from 2029 to 2033, while Leonard was only ordered to pay the league $700,000.

While Leonard won't face any suspension from the league, which gives the Raptors the clarity they need to proceed with the June 30 trade, this new federal probe puts another cloud over getting this already-delayed trade done.

With Ballmer and Clippers president of basketball operations Lawrence Frank suspended from league activity, Los Angeles is reported to be trying to find a sense of organizational structure —  someone who can make decisions on behalf of the franchise for the foreseeable future, which includes accepting this trade.

Though this new federal investigation could delay that process even further.

The New York Times report says the franchise and Ballmer are still trying to figure out how to respond to the punishments handed down by the league. Among the potential moves they're considering is whether to bring a lawsuit against the NBA, asking a judge to issue a restraining order to stop the league from enforcing penalties the organization believes are unlawful.

The Kawhi Leonard trade to Toronto has been paused for two months. (Jayne Kamin-Oncea/Imagn Images)

So, what does all this mean for Raptors fans?

Will Kawhi be there at the end of this month for Media Day? Or wearing a Toronto jersey on opening night?

That depends on how quickly the Clippers can get their homework done.

Think of it as a pile of essays and assignments that the Los Angeles Clippers front office currently has to finish, some of which have a higher priority than accepting the Raptors trade.

This new Department of Justice probe is likely one of them, along with Ballmer and company potentially bringing forward a lawsuit to fight the NBA's disciplinary actions.

As the front-office cliché goes, a franchise should never shy away from acquiring a star if it can make the team better.

Though it's hard not to ask this question in hindsight: If the Raptors knew about all the headaches that would come with making this deal, would they still have pulled the trigger?

Despite the trade remaining in limbo, Brandon Ingram has been spotted training at Clippers facilities, while Leonard was in Miami for a Raptors mini-camp, doing individual workouts ahead of the start of training camp at the end of the month.

NBA insider Marc Stein reported on Thursday that the Raptors are eager to complete the trade as originally proposed after initially placing it on hold on July 9.

Leonard and his camp apparently share that belief as well.

So, when will the deal finally get done?

Well, that's just a question of how quickly the short-staffed Clippers front office can get its homework done.