Sports

Why Kawhi Leonard investigation is a risky win for the Toronto Raptors

The Clippers have plenty of reason for regret, even shame. 

How the Raptors will eventually look at all of this in the coming seasons is a question that only time can answer. 

A year-long NBA investigation prompted by journalist Pablo Torre’s Pulitzer Prize-winning podcast series detailing a parade of phony endorsement deals between Kawhi Leonard and various Clippers business partners designed to line Leonard’s pockets over and above his on-court income came to a dramatic conclusion on Wednesday. 

Why, yes, it turns out the Clippers bent over backward to make sure that Leonard — at the steady urging of Dennis Robertson, the once and future Raptors star’s business manager and uncle — got paid a lot of money for doing nothing, this in addition to the hundreds of millions he earned for the 331 games (out of a possible 554) he played over his seven rocky seasons in Los Angeles. 

The Clippers are predictably aghast at the league’s findings — their lawyer went so far to call it a “witch hunt” — but a clear-eyed reading of the 35-page report prepared by the law firm hired by the NBA is both very entertaining (a Clippers executive texting another: “I cannot begin to tell you all the red flags with these deals. Just doing what I’m told at this point” is just one highlight) and conclusive: the Clippers cheated in order to circumvent the salary cap to Leonard’s benefit, full stop. 

Clippers owner Steve Ballmer can dig into his $150-billion fortune to sue the NBA as much as he likes, but it will be hard to discredit the findings that emboldened commissioner Adam Silver to delivering as stiff a penalty as the league can levy against a team and owner, short of forcing a sale of a franchise. The Clippers having to forfeit five first-round picks beginning in 2029 could cripple them for a decade, maybe more. 

That Leonard escapes all of this having to pay what amounts to only a $700,000 fine — presumably representing the value of the improper benefits the Clippers paid to him and his family for travel, gifts and tickets, is a minor miracle, given the report details no-show endorsement deals Leonard with four Clippers business partners were worth more than $60 million.

The NBA could have voided Leonard’s current contract ($50.3 million), which would have made him a free agent and likely available to sign for only a small fraction of his value, given the lack of available cap space across the NBA at this point in the off-season. In all, it could have been a penalty worth more than $100 million. 

Why the NBA treaded so lightly, we may never know: could it be the omnipresence of “Uncle Dennis” (who Leonard split with and who has since been banned from league activities for five seasons) provided plausible deniability regarding Leonard’s culpability? 

Did the league not want to fight the union as well as Ballmer (the NBPA signed off on the $700,000 fine) or did it simply not have the evidence that Leonard was up to speed on exactly why all these extra millions were flowing his way? 

But, safe to say, Leonard should count himself incredibly fortunate. 

But as the dust settles, should the Raptors? 

Should all of this provide a certain measure of satisfaction for Raptors fans, given the Clippers allegedly used (then unproven) promises of off-court earnings to help sign Leonard in free agency in the summer of 2019, just weeks after the future Hall of Famer led the Raptors to the NBA championship? 

Your mileage may vary on that. Leonard’s plan all along that season was to return to his Southern California home. Would the Raptors acquiescing to the reported requests for off-court income Leonard was making at the time (through Robertson) had made a difference? 

Doubtful, given the Clippers were both open to salary-cap shenanigans, were able to procure a co-star for Leonard in Paul George and were indeed in Southern California. 

But there is certainly a satisfying full-circle element to the Raptors being able to repatriate a player who led them to their greatest heights, and whose departure — especially under shady circumstances — robbed them of at least one more championship and maybe more. 

It’s tempting to view the conclusion of the NBA’s investigation as a win. The Raptors certainly do.

It clears the way for what will likely be the official consummation of the trade for Leonard that was put on hold in July until it was clear that his availability to the Raptors wouldn’t be compromised by the investigation’s findings.

So, book it: Brandon Ingram and Grady Dick to the Clippers, along with a 2027 first-round pick swap and unprotected first-round picks in 2031 and 2033, as well as second-round picks. 

Shortly after that, we can expect the Raptors to sign Leonard, who just turned 35, to a contract extension that could be worth up to $123.7 million that would cover the 2027-28 and 2028-29 seasons on top of the $50.3 million Leonard is owed this coming season. 

But now that the Raptors have their man, the risk they’ve taken to remain competitive in a significantly improved Eastern Conference comes into full view. 

Leonard remains a brilliant player — he averaged a career-high 27.9 points per game along with 6.4 rebounds and 1.9 steals on very nearly 50/40/90 shooting splits over 65 games last season. 

But he’s forever an injury risk and has played in just 56 per cent of his team’s games over the past nine seasons, going back to his last year in San Antonio, where issues around his knee and thigh prompted him to split with the Spurs in the first place. 

No one knows better than the Raptors as to what Leonard is capable of at full steam. His 24 playoff games during their title run were among the greatest individual performances in league history. 

But as exciting as re-acquiring Leonard might be, it will be impossible to watch him this season and beyond without thinking his next significant injury could be his last. 

It’s a gamble the Raptors are willing to take because he represents a significant improvement over his replacement, Ingram, and the most direct path they could possibly take to being a factor in the East this season and even a fringe contender for an NBA Finals appearance. 

But it’s a gamble. When it was clear Leonard and the Clippers were going to be parting ways, the stoic star put out messaging that he was willing to sign an extension only with the Raptors, which understandably tamped down the trade market for one of the NBA’s true difference-makers, but two unprotected first-round picks and a pick swap is just shy of the price the Miami Heat paid to acquire 31-year-old Giannis Antetokounmpo and less than what the Philadelphia 76ers paid as part of the package to acquire 29-year-old Jaylen Brown. 

Having Leonard signal he was determined to facilitate a Raptors reunion was a nice sugar high at the time. But now that the deal is real, there is the possibility for a sugar crash as well: Leonard is a tremendous on-court fit for any team serious about competing with the NBA’s elite — but was Leonard’s determination to return to Toronto a reflection of his true feelings about the city and the organization, or a savvy play to secure one more pay day in a league that looked at his injury history, age and off-court baggage and didn’t think there was nearly $200 million of value there? 

“Board man gets paid” was a Leonard catch phrase from his college days that went viral when it resurfaced during the Raptors championship run. 

It couldn’t be more apt. 

Leonard got paid and then some by the Clippers. He’s going to get paid again by the Raptors. 

The Clippers have certainly paid the price for going too zealously into the Leonard business. 

Now that the NBA’s investigation into that mess has concluded, we’ll find out if the Raptors will get a return on their investment.

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