Kawhi Leonard is back with Raptors, and as we celebrate the return of the basketball star who ushered the Larry O’Brien Trophy to a non-U.S. city for the first time in history, maybe we should push the details of the transaction to the back of our minds.
The first time Leonard joined the Raptors, he arrived as part of the blockbuster trade that sent franchise cornerstone and fan favourite DeMar DeRozan to the San Antonio Spurs. Then he left as a free agent as soon as humanly possible, returning home to Los Angeles, to the prospect of teaming up with his buddy Paul George on the Clippers, and to the possibility of some juicy non-salary perks, which we’ll explore later.
But if we meditate too long on the fact that Leonard has never chosen to play in Toronto, we risk rubbing lustre off the Raptors’ gleaming new acquisition. And dwelling on that circumstance any further just reminds us of the ego-bruising reality of life on the losing end of the rivalry between Toronto and Los Angeles.
Toronto lost Rocket Ismail to the Raiders and Leonard to the Clippers.
Baseball megastar Shohei Ohtani strung the city’s sports fans along in December 2023, as he sought a landing spot after his departure from the L.A. Angels. We all watched that private jet’s flight path as it crossed the continent bound for Toronto, but Ohtani wasn’t on board. He would move, eventually. Across town, to the Dodgers, who last fall defeated the Blue Jays in an all-time classic World Series.
In between all that, Kendrick Lamar put Drake in a hammerlock, then showed up in Toronto for two sold-out shows.
So, given that Leonard didn’t exactly choose Toronto, his return is less a win than a windfall for local sports fans. But it’s a giant step forward for a franchise with championship ambitions and, combined with this week’s ceremonial signing of Raptors legend Kyle Lowry, is a timely boost to fragile sports egos both locally and nationwide.
Kyle Lowry signed a one-day contract and formally ended his NBA career as a Toronto Raptor with surprise appearances from Kawhi Leonard and Vince Carter. Lowry spent nine years as a Raptor and helped lead the team to its 2019 championship.
Our men’s national soccer team might have folded after showing early promise in a knockout-stage match against Morocco, which has emerged as a legit global power. And we’ll have to wait four more years to see if this year’s run to the World Cup’s Round of 16 was Canada’s peak, or a declaration that we’ll be knockout-stage regulars. But Leonard’s return to the Raptors figures to pay dividends this year.
After all, Leonard, who just turned 35, is coming off the best season of his career by a long list of statistical measures. Last season he averaged a career-best 43.3 points per 100 possessions. By comparison, he put up 37.5 the year he led the Raptors to the NBA title. His career average 32.5. So it’s not hyperbole to say Leonard played at a championship level in 2025-26, and if he repeats that performance next season the Raptors are poised for a deep playoff run.
And if you’re paranoid that Leonard will develop a wandering eye after another successful campaign in Toronto, his new agent, Harrison Gaines, is already reportedly negotiating a contract extension with the Raptors. That’s a key point, because this time Leonard arrives in Toronto with some baggage.
As reported first, repeatedly and painstakingly by the Pablo Torre Finds Out podcast, Leonard was at the centre of a fake endorsement scandal involving his reps, the Clippers, and a company called Aspiration. In the briefest summary, the Clippers helped facilitate an eight-figure endorsement deal between Leonard and Aspiration, except the contract didn’t require the basketball star to work for the money. Viewed as a money-for-nothing plot, it also looks like a caper aimed at circumventing the NBA’s salary cap, which could make Kawhi/Clippers/Aspiration the biggest non-gambling NBA scandal in recent memory.
And the Toronto Star has reported in the past that Leonard’s former rep, his uncle Dennis Thompson, tried to extract similar off-the-books bonuses from the Raptors back in 2019. The Raptors opted not to play ball, and Leonard took his talents to Los Angeles.
The word “former” in the previous paragraph carries weight. Leonard changing agents and teams could represent an effort at a clean break from the Aspiration pay-for-no-play debacle. If reporters ask the Clippers about it, the team can say, truthfully, that the player in question is no longer on the squad. And the Raptors can say, truthfully, that they’ve always followed the rules, and that they weren’t involved in whatever happened in Los Angeles.
And if you’re a Raptors fan, and the team is winning with a resurgent Leonard, you might not want anybody asking probing questions about the mess Leonard left behind with the Clippers. Maybe you just want to recapture the feeling that washed over you when Leonard hit “The Shot,” that jumper from the right corner that bounced high and rattled around the rim before falling through the hoop at the buzzer to vanquish the Philadelphia 76ers and send the Raptors to the Eastern Conference Finals.
A physicist explains how Toronto Raptors’ forward Kawhi Leonard made the shot that beat the buzzer in Game 7 to win against the Philadelphia 76ers.
If you remember that play, you might also recall that one of the first teammates to congratulate Leonard in the post-game frenzy was Kyle Lowry, who on Tuesday signed a one-day contract with Toronto so he could retire a Raptor.
Like Leonard, Lowry arrived in Toronto via a trade. In July 2012 the Houston Rockets shipped him here in exchange for Gary Forbes. But unlike his superstar teammate, Lowry chose to return to Toronto for the official end of his career. If you’re seeking an unspoiled feel-good story about a prodigal hooper finding his way back to Jurassic Park, this is it.
At his peak, Lowry never ranked alongside Leonard or Steph Curry or LeBron James among the league’s top-tier elite, but he’s always been steady and smart and dependable and durable. A 6-foot-3 point guard needs to be all those things to last 20 years without being a lights-out scorer.
And where Leonard has The Shot, Lowry has The Hug.
Moments after the Raptors clinched the 2019 NBA title, and people flooded to the court and celebration, Lowry spotted an altercation percolating between Masai Ujiri, then the team’s president, and overzealous security guard using physical force to keep Ujiri on the sideline. The point guard sprinted over, wrapped his arms around Urjiri and guided him away from danger, and toward his celebrating teammates.
The biggest assist of his career.
And this Tuesday’s one-day contract is the happiest ending possible.
I don’t know what will happen with the Raptors when the NBA season tips off in October, but between repatriating Leonard and bringing Lowry home, they’ve already won the summer.
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