Sport 9 min read

Why the Kawhi Leonard contract investigation is taking so long

The players’ union isn’t happy. Pablo Torre has found out something else, and Kawhi Leonard remains — officially — a Los Angeles Clipper.

The second half of July and most of August is the only dormant period on the NBA calendar. For most of the rest of year, there is always something going on. 

But the saga around the Los Angeles Clippers and Kawhi Leonard — which the Toronto Raptors are now officially embroiled in due to their decision to trade for the aging superstar, bringing him back to the franchise where he won an NBA championship in 2019 — refuses to go away. 

For those who haven’t been following or have sensibly chosen the “tell me when it’s over” approach: the NBA league office has been investigating the Clippers for the possibility of salary-cap circumvention for going on 11 months now. 

Maybe NBA commissioner Adam Silver, a lawyer by training and thus no stranger to the nuance and specificity of language, was sending not-so-coded signals when he said earlier this month, regarding the investigation: “My timeline remains this summer,” without explicitly acknowledging that “summer” isn’t over until Sept. 22, or six days before the Raptors open training camp. 

But a report from ESPN on Wednesday suggested that might be optimistic, as the tentacles of the investigation around the four-year, $176-million contract Leonard signed with the Clippers before the 2021 season keep spreading, all prompted by a series of Pulitzer-prize-winning podcasts by Pablo Torre beginning in September 2025. 

Wednesday’s ESPN story by Baxter Holmes cited sources close to the NBA Players Association that suggested the entire process could drag into 2027 if the Clippers and NBPA didn’t accept whatever findings and proposed remedies by the league office once the investigation is included.

I’m not suggesting that the NBPA isn’t being sincere in its determination to fight for one of its members, but does anyone really believe the NBA or anyone else involved — all who stand to gain if the league’s business grows with a robust 2026-27 season and lose if business suffers — is going to let what Kawhi Leonard and the Clippers did or didn’t do in 2021 threaten a single dollar of revenue five years later?

A fair interpretation of this is that the NBPA, whose interest is in making sure that Leonard is protected from anything that might affect his earning power — a suspension, the possibility (however remote) of his contract being voided, or an upcoming extension worth as much as $124 million he could sign with the Raptors — is sabre-rattling and sending a reminder to Silver and the league office that it won’t be a silent bystander to the entire process. 

Some background: the NBPA is under new leadership, with newly installed executive director David Kelley conceivably doing some early table setting in advance of new collective bargaining agreement talks that could begin as soon as the summer of 2029. Kelly has already signalled that the players will be looking for amendments to the current deal, ratified in 2023. 

Meanwhile, the Clippers, owned by Steve Ballmer, who sits on a personal fortune that approaches $150 billion, depending on how Microsoft shares are performing on a minute-by-minute base, have signalled loudly that they have done nothing wrong. They have denied the allegations made by Torre that they used the team’s sponsorship relationship with now-defunct environmental bank Aspiration to funnel secret money to Leonard’s camp and instead were themselves duped by Aspiration founder Joe Sanberg, who has since been convicted and imprisoned on multiple accounts of fraud. 

This was all stewing in the background when Silver spoke after the NBA’s board of governors meeting on July 14. He doubtless understood the possibility that the conclusion of the investigation didn’t mean the situation could be put to bed, knowing that the NBA’s CBA allows for an arbitration hearing if whatever conclusions or penalties provided by the league office aren’t accepted by the involved parties, that there was still the potential for an appeal process after that. 

Lay all that out there alongside the fact that both the Clippers and the NBPA are strongly signalling that they will fight findings they don’t support, and it’s easy to see how this entire affair could drag past summer, into the fall and through next winter. 

And what if the whole thing spills over into the courts?

And did we mention that since Silver spoke in Las Vegas on July 14, The Athletic published a report that the investigation is looking into a second potentially problematic endorsement deal? Or that Torre dropped another episode on Wednesday detailing a strange investment vehicle where Leonard, his former agent and his uncle, became minority owners in a Rhode Island-based minor-league soccer franchise with tangential ties to Ballmer and the Clippers?

For Raptors fans mainly interested in whether Leonard — whose trade to Toronto is paused as the Raptors wait until the league’s investigation is resolved before completing the deal — will play in Toronto this season, the bottom line as I see it is this: 

Leonard will be with the team in training camp on Sept. 29 in Quebec City. 

Granted, that’s just me trying to make sense of the whole thing, but here’s why that’s my view: 

If the law firm investigating the Clippers on behalf of the NBA has definitive evidence that the Clippers and Leonard circumvented the salary cap, they likely would have provided their findings months ago. 

Which isn’t to say Torre hasn’t compiled a convincing series of findings that are hard to rationally explain as anything other than an effort by the Clippers to circumvent the cap. Just that if Silver and the NBA are going to go after Ballmer, one of the most respected and influential owners in the league, they aren’t going to do it without the goods. 

If the investigation — which the NBA league office is paying for — somehow can’t nail down the precise details needed, maybe there is enough circumstantial evidence to punish the likes of Leonard’s former agent or uncle, Dennis Robertson. Maybe the Clippers sacrifice a front office executive and a couple of second-round picks and Ballmer pays a fine, or makes a charitable donation.  

That done, there would be no need for time-consuming arbitration and appeals, and everyone can move on. 

But what if there is a smoking gun, and irrefutable evidence surfaces that Ballmer and the Clippers were up to his elbows in it, pulling out all stops to make sure that Leonard and everyone around him got paid? And that Leonard was right there with him, waiting to get his massive hand greased?

Wouldn’t that make it more likely, not less, that the investigation would wrap up sooner than later? 

After all, at that point Silver would have considerable leverage to have everyone concerned agree to the lightest possible set of penalties that they can agree to with a straight face. 

The last documented case of salary cap circumvention in the NBA dates back to 2000, when it was discovered that the Minnesota Timberwolves had a side deal with Joe Smith that they would have him sign three one-year contracts at the league minimum so they could have more roster flexibility around Kevin Garnett in exchange for a plan to sign Smith to a long-term deal for $86 million. 

Then-NBA commissioner David Stern stripped Minnesota of five first-round picks (later reduced to three) and barred then-owner Glen Taylor and then-general manager Kevin McHale from the team for a year.

With that as precedent, maybe the resolve by the NBPA and the Clippers to go through the arbitration process, knowing that the facts all point in one direction, would weaken, and some kind of middle-ground punishment — a symbolic suspension for Leonard, a fine for Ballmer and maybe the forfeiture of a future first-round pick or two (the Clippers will have two extra belonging to the Raptors if and when the trade is finalized) — will seem like a good deal for all involved. 

Could that get figured out over a few conference calls over Labour Day weekend? Seems reasonable. 

Looming over all of this is the reality of what the interested parties stand to gain if the investigation and its aftermath are wrapped up (relatively) quickly and quietly, and stand to lose if it drags on. 

The NBA would doubtless love to highlight Leonard’s return to Los Angeles as part of its national TV package as it figure out its schedule, and having Leonard and the Raptors slugging it out in a suddenly loaded Eastern Conference — Leonard vs. LeBron and the Sixers, Leonard vs. Giannis and the Heat, and the rest of it — wouldn’t be a nice bump to primetime TV ratings. 

Meanwhile, keeping the peace with Ballmer and allowing the Clippers to move on to their next competitive iteration in one of the league’s glamour markets seems more win-win for the NBA than getting into a protracted legal battle with someone with unlimited funds for litigation who also sits on multiple essential league governance committees. 

And what of the poor Raptors, who lost out on their best chance to defend their 2019 NBA title when Leonard left for the Clippers in free agency that summer (amid allegations even then of extra inducements that the league investigated) and could potentially lose out on a reunion if the league opts to go scorched earth here? 

Is the NBA really going to let the Raptors get burned twice?

For everyone concerned, finding a way for Leonard, the NBA and the Clippers to save face and move on to new business is overwhelmingly the best outcome for everyone. 

So, sure, this thing seems like it’s dragging on, but it’s hard to imagine it doesn’t end up in with Leonard as a Raptor; the league with this scandal behind it and the Clippers perhaps with their knuckles rapped but otherwise free to move forward. 

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