The Better Question: Kawhi Leonard’s stalled return to Toronto

Aug 5

CAFÉ MANSHA | Issue No. 2

What better question is there to ask?

By Jagneet Malhotra

08/05/2026

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Kawhi Leonard was reportedly coming back to Toronto. Then the trade stalled.

Seven years after he helped deliver the Raptors their first NBA championship, Toronto reportedly agreed to bring him back. As a Raptors fan, I wanted that story. I could already picture another infamous press conference, highlights of the iconic shot, and the hype surrounding another championship run.

Maybe that made me too willing to rush past the part that didn't fit.

Kawhi hadn't failed a physical. There was no new injury. His age, contract, medical history and championship pedigree were well-known. Nothing about the player had changed.

The uncertainty around him had.

The NBA was still looking into allegations that the Los Angeles Clippers had worked around the salary cap through an endorsement agreement involving Aspiration, a financial technology company in which Clippers owner Steve Ballmer had invested. The Clippers denied wrongdoing. Kawhi denied wrongdoing. At the time of writing, the league still hadn't reached a final decision.

Toronto wouldn't inherit whatever penalties the league might impose on the Clippers. The risk was a little different. The Raptors would be trading for a player whose contract or availability could still be affected by a decision they didn't control.

So the trade hadn't stalled because Toronto suddenly knew less about Kawhi the basketball player. It stalled because the team couldn't know what the investigation might still change.

That's what stayed with me.

I found the headlines and media pundits arguing to death about a verdict. Was the endorsement real? Was someone trying to move compensation around the cap? Who was right? I wanted those answers too. The problem was Toronto had to decide before the NBA gave them one.

My first thought was that the league had a compensation problem.

That version of the story made sense to me. A player performs. A team pays him. The amount sits in a contract, the contract counts against the cap and everyone can see the number.

Except that isn't where the financial life of a modern athlete ends anymore.

Salary still matters. It may just be the beginning. Equity, advisory work, commercial partnerships, private investments, ownership opportunities and introductions to founders can all become part of a career. Some opportunities show up because the player is famous. Some because he's earned trust. Some only exist because basketball put him in a room he never would've entered otherwise.

I kept thinking the Collective Bargaining Agreement (CBA)’s definition of compensation had fallen behind the play it was trying to regulate.

It sounded right. At least to me.

Then I called my friend Layth. He laughed and said, “Go read Article XIII”.

Layth Gafooris a sports and entertainment lawyer from Toronto. I called because I wanted legal grounding. I wasn't asking him to decide the case. Still, I thought I knew what the article was about before we spoke.

Within a few minutes, I knew I didn't.

Every time I tried to land the plane, Layth pushed me back into the facts. CBA doesn't stop at the number written in the player contract. Salary and compensation have defined meanings, but Article XIII also lets the league examine arrangements that might deliver team connected value outside the contract. The payment doesn't have to come straight from the team. Calling something an endorsement doesn't settle what it actually does.

The league had already thought about compensation coming through another door.

That bothered my theory.

I kept looking for a missing definition because it was a clean problem. The more I read, the less clean it became. Maybe the harder issue wasn't defining compensation. Maybe it was deciding what a particular opportunity was really worth, who had created it and whether it existed because of basketball.

A normal endorsement gives the league something to compare. It can look at the work performed, the player's commercial profile, the length of the deal and what similar companies paid similar athletes. It can ask whether the agreement was negotiated independently, whether the work was done, whether the amount was close to fair market value and whether anyone tied to the team sourced, funded, guaranteed or steered it.

Equity doesn't sit still like that. Neither does access. An introduction may be worth nothing today and change a life ten years from now.

By then Layth and I weren't really talking about compensation anymore.

We were talking about judgment.

How do you make a good decision when nobody can yet know the full value or the full risk?

That question followed me into the rest of this article.

What exactly is a player negotiating for?

A salary comes with a number attached. An opportunity usually doesn't.

Imagine two players making the same salary. One receives his contract income and a normal group of endorsements. The other earns the same salary, but basketball also introduces him to founders, private investments, ownership groups and people who've built companies before.

The cap records them as equals. Their economic lives after basketball could look nothing alike.

That doesn't make the second player's opportunities improper. A company may honestly value his name and reputation. An advisory role may involve real work. An investment may be offered on terms available to other qualified investors. A relationship that began through basketball can still become a legitimate opportunity outside it.

The league and the player are still looking at that opportunity from opposite sides.

The league has to ask whether the opportunity is really compensation connected to basketball. The player has to ask whether it's real value or just feels valuable because of the room, the people and the attention around it.

Both are trying to price a future that hasn't happened yet.

Somewhere around here, the Kawhi saga stopped feeling like a story about one endorsement agreement.

Toronto already knew Kawhi was a great basketball player. The Raptors were trying to understand what else had to stay true for the trade to work the way everyone expected.

Would he be available? Would the contract remain intact? Could a league decision affect him after the trade? How long could the uncertainty continue? What downside would Toronto accept before it knew the answer?

Those are trade questions. They're career questions too.

Every meaningful opportunity arrives with uncertainty about what it might become. A founder explains the market. An investor talks about the upside. An advisor tells you who else is involved. The room feels important because important people are sitting in it.

That can be intoxicating.

It can also make a weak structure feel stronger than it is.

I started asking a simpler question: what has to be true for this opportunity to become as valuable as it looks?

Once I asked that, the invitation mattered less than the structure around it.

Why does the opportunity exist? Would it exist if I didn't play basketball? What work am I expected to do? Who controls the outcome? What am I risking besides money? What do the people offering it gain from my involvement? What still belongs to me if the relationship changes?

Those questions won't guarantee a good decision. They aren't supposed to.

They show you where the uncertainty lives.

That seemed to be what Toronto was doing. The Raptors weren't waiting for a perfect future. They were refusing to act as though an unresolved risk didn't exist simply because the opportunity was attractive.

Remarkable careers usually aren't short on invitations. The harder part is deciding which commitments deserve to be made.

The modern athlete hears the same advice all the time. Think beyond the game. Build a brand. Invest early. Own equity. Start a company. Join a fund. Become an owner one day.

Most elite players already understand that. They don't need another person telling them to invest.

They need discernment.

Not every room is worth entering. Not every association creates credibility. Not every equity grant creates meaningful ownership. Not every famous founder is a trustworthy partner. Not every opportunity that feels exclusive is scarce for a good reason.

Saying yes to everything basketball makes possible isn't the same as maximizing a career. The real work is learning which possibilities deserve a commitment.

What stayed with me from Layth's legal framework was how useful it became once we moved outside the legal question. Fair market value. Independent purpose. Economic substance. Disclosure. Arm's length terms. Work actually performed.

A league can use those ideas to separate a legitimate business arrangement from hidden compensation. A player can use them to separate a durable opportunity from a flattering proposition.

I stopped paying as much attention to the title on the agreement. I started asking what the arrangement actually did.

Who creates the value? Who controls it? Who keeps it if the circumstances change? Do the economics still make sense without the story being used to sell them?

The strongest advisors don't make every decision for the people they serve. They improve the questions surrounding the decision.

That's what Layth did for me. I called him expecting to talk about whether the NBA's definition of compensation was broad enough. He helped me see that the rulebook had already anticipated much of what I thought was new.

What remained hard was making a sound decision when the value was uncertain, the incentives overlapped and the answer might not become clear for years.

The NBA has its own version of that problem. It has to protect competitive balance without treating every legitimate business opportunity as suspicious. Players should be able to build companies, make investments and take part in the ownership economy around professional sports. Hidden compensation can't be dressed up as entrepreneurship. Entrepreneurship can't automatically be treated like hidden compensation because a player's network overlaps with a team owner's.

I don't know where the next CBA will land. I do wonder whether the answer will be less about writing one more broad definition and more about process: better disclosure, clearer safe harbours, independent valuation and faster decisions.

Toronto's pause showed what happens when clarity doesn't arrive in time.

The Raptors understood Kawhi's basketball value. What they couldn't price was the range of outcomes connected to an investigation they didn't control. They knew the player. They didn't yet know the complete transaction.

Nothing about Kawhi Leonard had changed.

Toronto's confidence in receiving everything it expected from him had.

That's why the trade stalled.

The NBA will eventually decide what happens in this case. Its ruling may tell us whether anyone crossed a line. It may also give players, teams and advisors a clearer sense of how similar arrangements will be treated in the future.

Players don't have to wait for that decision to take something from the story.

A career creates more than income. It creates visibility, trust, relationships and invitations. Some invitations will be ordinary. Some will waste time. A few could become the foundation for everything that comes after basketball.

The hard part isn't getting invited into the room. It's understanding the room before the moment passes.

When the jersey is hung up, what will still belong to the player?

The salary will have been earned. The games will have been played. The contract will have expired.

What remains might be the ownership he acquired, the judgment he developed, the people who still answer his call and the businesses he learned to build without the jersey.

Access alone won't create those outcomes. The decisions made after access arrives might.

I started this article with a headline about Kawhi coming back to Toronto.

The public question was whether the Clippers and Kawhi had crossed a line. My question was whether the NBA's definition of compensation had fallen behind the modern athlete. Toronto was asking something more immediate: what uncertainty are we taking on if we say yes before the facts are settled?

By the end, I wasn't thinking only about basketball anymore.

I was thinking about every opportunity that had looked obvious from the outside and felt much less obvious once I was the person who had to commit.

Negotiation can improve the terms of a deal. Better questions can help you decide whether it's the right deal in the first place.

Maybe remarkable careers won't belong to the people who received the most invitations or said yes most often.

Maybe they'll belong to the people who learned to pause and ask one more question before they committed.

Acknowledgements

Special thanks to Layth H. Gafoor (@laythgafoor) for his generosity, insight and willingness to challenge the assumptions that shaped this story.

Our conversations started with a legal question and became much more useful. Layth kept slowing the thinking down, adding nuance and helping me separate what was known from what still required judgment. This story is better because of his contribution.

About Layth H. Gafoor

Layth Gafoor is the founder and Managing Partner of Lucentem Sports & Entertainment Law P.C., a Canadian firm recognized by Legal 500. A former competitive boxer and IBM executive track professional, he entered law to combine his interest in business with helping athletes reach their goals. He earned his undergraduate and law degrees from York University and Osgoode Hall Law School. Gafoor advises athletes, agents, brands and sporting organizations on contracts, name, image and likeness matters, crisis management, media training, governance, immigration and taxation. He also oversees Lucentem Media Group, which supports athletes and influencers with marketing and brand development, and has served as President of the Sports Lawyers Association.

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Primary sources and further reading include the 2023 NBA Collective Bargaining Agreement, particularly Article XIII and related provisions on compensation and circumvention; the NBA Constitution and By-Laws; reporting from Reuters and The Athletic on the reported investigation and trade discussions; NBPA resources on the CBA and player business opportunities; and research on judgment and decision making under uncertainty from Harvard Business Review.