In professional sports, athletes have to look out for themselves. Opinions are thrown at them from every direction, like which players they should team up with, whether to stay with their current team or look for a better situation.
It is up to the players to make the decisions they believe will benefit them the most. The tricky part: what might seem like a great choice in the moment could turn into a never-ending game of “what ifs” had things gone differently.
No greater decision in the NBA exemplifies that more than Kawhi Leonard’s departure from the Raptors in 2019.
Kawhi Leonard Was a Star with the Spurs
After the San Antonio Spurs won the NBA title in 2014, Kawhi began emerging as a star in the league. He had just been named Finals MVP on a squad with Tony Parker and Tim Duncan, becoming the second-youngest player ever to win the award.
Over the subsequent three seasons, he became an All-Star, won Defensive Player of the Year twice and was the runner-up for MVP. With the Spurs’ big three nearing the end of their careers, Kawhi was primed to take over the keys to the franchise.
But things changed after he got injured in the 2017 playoffs.
He sprained his left ankle in the Western Conference Semifinals against the Rockets. Then, he reaggravated his ankle in the following series after landing on Zaza Pachulia’s foot. The latter injury would change the course of Kawhi’s career and the franchise’s trajectory.
In the midst of recovering from his ankle injury, he developed tendinopathy in his right quad, which kept him out for the start of the 2017-18 season. He played just nine games that year before being ruled out again with tendinopathy in January. Kawhi never returned to play another game as a Spur.
The Fallout Between Kawhi and the Spurs
The presumed consensus surrounding why Kawhi demanded out in 2018 was that his relationship with the organization had fizzled. Throughout his time injured, people in the organization questioned his commitment to the team and undermining the severity of his ailment.
As his timetable to return kept getting pushed back, Tony Parker was skeptical of just how badly his teammate was injured. Parker suffered a quad injury in the past, and seemingly cited his shorter recovery period to delegitimize his injury. He also disparaged Kawhi’s decision to consult several medical opinions outside of the Spurs’ medical staff.
“It was a rehab for me for eight months,” Parker said, comparing his length of absence to Kawhi’s. “Same kind of injury, but mine was a hundred times worse.”
Head Coach Gregg Popovich was then asked if he thought Kawhi could return before the end of the 2018 season. His response marked the official burning of a bridge that had all but crumbled.
“You’ll have to ask Kawhi and his group that question,” he remarked. “So far, they say that he’s not ready to go. So we can’t do anything until that happens…”
Hearing those words rubbed Kawhi the wrong way.
Parker and Popovich’s comments told the whole story about the falling out: They had grown tired of waiting for Kawhi’s personal team to clear him to play because he had already been given the green light by the team medical staff.
The Raptors Had a Roster Built to Compete
Kawhi’s trade to Toronto in the summer of 2018 was shocking for numerous reasons. First, the Raptors dealt one of their franchise players, DeMar DeRozan, without any warning after assuring him he wouldn’t be moved. Second, Toronto was not on the list of top destinations Kawhi wished to be sent to.
The San Diego native made it known that he didn’t intend to stay with Toronto for the long haul. But winning a championship in his first season there felt like the kind of caveat that could alter his decision.
On paper, everything was set up for Kawhi to re-sign. The Raptors had an up-and-coming bench unit and several players on the verge of breaking out. Four players – Norman Powell, Pascal Siakam, OG Anunoby, and Fred VanVleet – were on the come-up. They have all gone on to either win an NBA championship, reach the finals, or make the All-Star team.
“Everything was positioned perfectly,” fellow 2019 NBA champion Fred VanVleet said.
Kawhi Left a Great Situation
In addition to the talent of the roster, the medical staff had reached a great synergy with Kawhi. They created a plan of load management to ensure he was ready and healthy come postseason.
Still, his teammates knew his intention was never to be there long-term.
“He said it from day one. ‘I’m not staying here,’” VanVleet relayed. “So from day one…’I don’t know why they traded for me. I don’t want to be here. I’m not staying here.’”
Regardless of what Kawhi stated at the beginning of the season, there was a glimmer of hope he might stick around when the city rallied to persuade him.
Restaurants and businesses promised free meals to him if he affirmed his commitment to the city. Additionally, Toronto offered him more than the L.A. Clippers – a max extension of five years, $189.7 million.
He said no to both.
That is where the X-Factor behind the star’s decision-making comes into play.
Family Interfering in Business
In comes Dennis Robertson, also known as Uncle Dennis. After Kawhi’s dad was shockingly murdered when Kawhi was little, Uncle Dennis became a father figure. Uncle Dennis is more than just an uncle to Kawhi; he is his manager and a primary voice in many of the business deals made by his nephew.
It is not unheard of for family members to be a part of athletes’ business decisions. But his influence may have been overbearing. While it was reported that Kawhi picked the L.A. Clippers so he could play closer to home, there’s more to the story.
Many sources divulged that Dennis suggested outlandish demands to Toronto when Kawhi was making his free agency decision. Among his requests were a trade for Paul George to pair alongside his nephew, and a piece of ownership in the Toronto Maple Leafs and other companies affiliated with Maple Leaf Sports and Entertainment. But sports teams are prohibited from negotiating deals with team sponsors.
He then demanded a minimum of $10 million annually from sponsorships.
What’s worse is that the same saga Kawhi found himself in with the fraudulent Aspiration deal occurred back then. Robertson and Kawhi’s team made it known that they didn’t want Kawhi to fulfill any obligations typically associated with sponsorship deals.
Danny Green, a teammate for eight seasons with Kawhi in Toronto and San Antonio, believes Dennis played a substantial role in Kawhi’s exit from the Spurs, too.
“His uncle had a lot of (influence on) what to do, what was going on, off the court…,” he said on All the Smoke. “I think once his uncle saw some distasteful things–in his mind, it was like, ‘alright, we not doin this…’”
What Could Have Been
Between Kawhi finding himself under fire for under-the-table scandals and his tenure with the Clippers proving underwhelming, he should have never left Toronto.
Kawhi did receive his wish with the Clippers when they brought in Paul George to be his running mate. However, forming the star duo came at a hefty cost.
The Clippers mortgaged a haul of future draft picks and shipped 2025 MVP Shai Gilgeous-Alexander to the Thunder in exchange for George. Despite missing the playoffs in three seasons and undergoing a complete rebuild, Gilgeous-Alexander’s Thunder went farther than George and Kawhi were able to go. The Thunder won a championship; George and Kawhi reached the Western Conference Finals once in five seasons.
Back in Toronto, Kawhi was living a professional athlete’s perfect dream: He was a franchise cornerstone surrounded by emerging stars and a trusted team of medical professionals. Who knows how far the team could have gone if they had stayed together?
According to VanVleet, the Raptors squad had dynasty potential.
“Three-peat, for sure,” he said of what the group would have accomplished with Kawhi. “It was just a perfect group of individuals, and we all understood everybody had the right mindset for their roles. I think definitely we would have won a few more.”
The Raptors were loaded with defensive and offensive talent. Their player development was second to none, shaping second-round picks and undrafted players into NBA starters.
Kawhi Could Reunite with the Raptors
Amid reports that the Raptors are interested in the two-time Finals MVP and the Clippers may be unwilling to extend him, it is time for Kawhi to return to Toronto. On each of his two stops before coming to Canada, Kawhi–or his uncle–thought the next place would be better. Though he won a title immediately after leaving the Spurs, his rapacious desires may have finally caught up to him.
Toronto gave him a second chance to rise from the ashes and remind the world of the superstar he is.
The grass is not always greener on the other side. And now, Kawhi Leonard is learning that the hard way.
Leave a comment