They say good things come to those who wait. The love affair between the Toronto Raptors and Kawhi Leonard is seemingly the best example of that. Back in 2018, when Leonard’s availability was a big question mark due to injuries, the then-general manager Masai Ujiri took a big gamble on the forward. He traded the most-liked stars of the franchise, DeMar DeRozan and Kyle Lowry, and much more, to the San Antonio Spurs for Leonard. While he was expected to miss a year, when Leonard entered Toronto, he was everything the team wanted and more. A 2019 championship title proved as much. Fast forward to now, after the entire look of the Raptors from top to bottom has changed, one thing remained: their belief in Leonard.

This summer, the forward was stuck in what seemed to be an endless controversy with the NBA. Very likely, he was again going to miss a season due to suspension. The Raptors took another gamble, hoping they would win again. And while Leonard isn’t exactly looking to win the championship title this year and came to Toronto for a personal reason, he still got a contract that made him a winner after all because “Board man gets paid,” and how!

Yesterday, the seven-time All-Star has agreed to a two-year, $115 million extension with the Raptors. Interestingly, he gave up roughly $11 million compared with his maximum extension. Yet even after taking less, the new contract sends his projected career earnings soaring past several NBA icons, according to The Boardroom.

According to the projected salary figures through 2028-29, Leonard will reach roughly $541.1 million in total NBA earnings. That places him third on the list, behind only $591.1 million and LeBron James at $589.3 million. It effectively puts him ahead of big stars of the league as well.

Stephen Curry now follows at $532.7 million, while Joel Embiid sits at $516.9 million. Nikola Jokic is projected at $508.9 million, just ahead of James Harden at $508.2 million. There is an important catch, though.

The $541.1 million figure is a projection through the 2028-29 season. It does not mean Kawhi Leonard has already collected that amount. His extension is worth $115 million over two seasons, with a player option for 2028-29. He is already set to make $50.3 million during the 2026-27 season, meaning the deal gives him three years and approximately $165.3 million with Toronto if he exercises the option. The decision also came with a significant concession.

The two-time Finals MVP accepted about $11 million less than his maximum extension value. He also waived a $7.45 million trade kicker to help the Raptors with cap space.

ESPN’s Shams Charania reported that Leonard expects to finish his career in Toronto, which could mean the player option ultimately serves as a mechanism for another deal. The 2028-29 player option gives Kawhi Leonard another decision point before he reaches 38. Fortunately, he is looking forward to just that.

Kawhi Leonard reveals two reasons he returned to the Raptors

Leonard’s short stay in Toronto last time was successful, to say the least. But more than the championship ring to boast about, he found something else: acceptance.

“This city took a liking to my family, and I took a liking to this city. I really liked it.”

In January 2026, when the LA Clippers went to Scotiabank Arena to face the Raptors, Leonard broke his long streak to avoid playing in that game. Later, he left the place before the reporters could enter the locker room. A day later, he was doing a very important task close to his heart.

He was at TAT Stadium in Scarborough, Toronto, to host a free basketball clinic for the Boys and Girls Club. They welcomed him just as warmly, with a mural of his series-ending buzzer-beater in the Eastern Conference semifinals against the Philadelphia 76ers on the court. Toronto mayor Olivia Chow was in attendance as Leonard also gifted the kids some New Balance apparel before sending them a heartfelt message.

“Toronto is still in my heart,” Leonard said in July. “My son was born out here, so he’s Canadian. He’s from Canada, so we always talk about bringing him back and showing him where he was born.”

And that’s the other reason Leonard wanted to return.

As I said, Leonard’s stay in Toronto was not long. But it was long enough for him to create some really good memories: a championship ring, a connection with the city, and most importantly, his son’s birth. And so, moving back to Toronto wasn’t even a question.

“My son was born here, and he’s been asking me forever when he’s going to come back. Now he’s back, and he’s able to see it rather than me tell him the great stories that happened.”

This is also a win for the Raptors. Despite the controversial ending in LA and an injury-marred time with the Clippers, Leonard’s last season there was rather impressive. He played in 65 games and averaged 27.9 points per game, the highest-scoring campaign of his 14-year career. He made the All-NBA Second Team and finished seventh in MVP voting.

So, in a win-win situation, Leonard might seemingly give the Raptors something more. After all, he has already promised the kids in that camp:

“Like I said, this won’t be the last thing. I’ll be doing something else out here.”