As the Kawhi Leonard investigation drags on, it's time to wonder if his trade to the Raptors will fall apart — CBS Sports

RESOLVING THE LEDGER

As the Kawhi Leonard investigation drags on, it's time to wonder if his trade to the Raptors will fall apart — CBS Sports | AIPROPX

Monday will mark the 11-month anniversary of Pablo Torre's first podcast about Kawhi Leonard , Aspiration and the possibility that the Los Angeles Clippers circumvented the salary cap in order to pay Leonard more than was legally allowable. You'd think that would mean we're nearing a resolution. NBA commissioner Adam Silver has even said that the league's investigation into the matter "needs to be wrapped up before the beginning of next season."

And yet, at least from the outside, a resolution doesn't seem imminent. After all, Torre released yet another podcast this week detailing Leonard's secret ownership stake in a soccer team in Rhode Island. Additionally, ESPN reported that this saga could drag into 2027 if the parties don't agree on the investigation's findings, and the Clippers, after all, are no longer the only team with a stake in the NBA's determination.

The Toronto Raptors agreed to trade for Leonard in June. They would later decide to put the trade on hold until the situation was resolved. Completing the trade would have meant absorbing the risk of any punishment for Leonard, though the reporting has largely been consistent in stating that both sides do eventually intend to consummate the deal. That is, until Thursday, when ESPN's Ramona Shelburne planted the first true seeds of public doubt.

"I can see a world in which Kawhi Leonard is back on the Clippers if this trade doesn't go through," Shelburne said on "NBA Today." "And the Clippers, quite frankly, are fine with that."

NBA training camps start in less than two months. The regular season starts in less than three. In a perfect world, this situation will be fully resolved in the coming weeks. But the longer this drags on, the less likely that will be the case. And if we do approach the season without answers, the Raptors will eventually have to make a decision here. At this point, there appears to be a real chance they will elect not to move forward with this deal.

So what's going on here? What is the holdup? What will inform Toronto's eventual choice? And is there anything the Clippers could do to grease the wheels here?

As far as we know, the NBA is still in the investigation stage. As long as this investigation has taken, it is only the beginning. The league cannot simply make a unilateral decision based on what the law firm of Wachtell, Lipton, Rosen & Katz finds.

If any of the parties involved here dispute their findings, the next step would be arbitration. The arbitrator would be jointly appointed by the NBA and the NBA Players Association, and would have the power to compel document production, witness testimony and order discovery. After that hearing, the arbitrator's ruling could be appealed to a three-person panel jointly appointed by the NBA and the NBPA. That appeal panel would finally have the power to make a binding decision.

We are still in the investigation phase here. The disciplinary phase, should the investigation's findings prove it necessary, has yet to begin and could take a fair bit of time. That process could theoretically be hastened through a settlement, but the immediate complication with any settlement is that three parties are involved.

The NBA is obviously one of them. The Clippers are another. But don't overlook the third notable party here: the NBPA. This is not simply a matter of protecting Leonard. The last thing the union wants is the NBA policing every sponsorship agreement that its players sign. Should the NBA decide that Leonard deserves to be punished, the NBPA would likely object.

This raises some pretty delicate points of conflict. The NBA has maintained 15 years of relative labor peace, but the NBPA has raised some very vocal concerns about the second apron and its roster-building restrictions recently. The current collective bargaining agreement can expire as soon as 2029. In a perfect world, the NBA would prefer to avoid a messy fight with the union before those CBA negotiations even begin.

It is possible that the NBA negotiates separately with Leonard and the Clippers, perhaps settling with one party and taking the other to arbitration. It's also possible that, through the investigation process, the NBA finds no wrongdoing it wants to act on.

The length of this investigation suggests that the NBA is attempting to be as thorough as possible, and that's probably the right decision. The details of the Leonard case are extremely public, and the evidence is, at the very least, compelling. There is a big difference between "compelling" and "actionable," but it's hard to imagine a team circumventing the salary cap in 2026 and leaving behind more breadcrumbs than Torre and his podcast team have dug up. If this investigation comes up empty, it essentially suggests that the bar for proving cap circumvention is so high that it is effectively impossible to punish, provided it is done with even a shred of discretion. In other words, it would be open season on cap circumvention.

That creates yet another purpose for this investigation. It's not just about Leonard or the Clippers. It has to be a deterrent, a signal to any other parties that might consider circumventing the cap that, if they do so, the league will leave no stone unturned in pursuit of punishment. Put all of this together and you have one of the most complicated investigations the league has ever undertaken. As impatient as the basketball world has been about this, the protracted nature of this investigation feels almost inevitable.

The Leonard trade was put on hold because formally executing it would have forced the Raptors to assume the risk of any punishments for Leonard. To be clear, only the punishments for Leonard matter for their purposes. The NBA is not going to strip Toronto of any draft picks for violations committed by the Clippers.

However, if the Raptors traded for Leonard and his contract were voided, they would still lose him and presumably the draft picks they traded for him (unprotected first-...