Kawhi Leonard is one of the biggest stars in the NBA, having won two NBA championships and Finals MVPs with the San Antonio Spurs and Toronto Raptors. But while his tenure with the Los Angeles Clippers has been disappointing, no one expected it to become this controversial thus far, a surprising turn of events for the quiet superstar. Here are the five most controversial moments linked to Kawhi Leonard, ranked.
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5. Kawhi Leonard's outlandish requests as a free agent in 2019

While the center of attention has been Leonard's no-show deal with Aspiration, in the process of that exposure, it seems that the Clippers star also had a controversial exit from the Raptors. It wasn't long ago when Leonard became the top free agent in 2019 after leading Toronto to its first franchise championship. Naturally, the 2019 Finals MVP earned plenty of suitors, especially with a reputation that he was disgruntled in Toronto.
However, that didn't mean that Leonard exactly wanted to burn bridges if the price was “right”. Leonard's uncle, Dennis Robertson, reportedly requested for ownership stakes from the superstar's suitors in free agency. Those suitors included the Raptors and Lakers. Naturally, all parties rejected the proposal.
To make matters more interesting, Leonard also asked for $15 million worth of endorsement deals from Raptors owner Larry Tanenbaum. Although the Raptors were able to get away unscathed, given that the deal didn't push through, a warning shot was made by Adam Silver on the free-agency matter. In the end, Leonard opted to join the Clippers.
4. Kawhi Leonard's Spurs exit

Leonard's NBA career started with the San Antonio Spurs. After the Indiana Pacers selected him 15th overall at the 2011 NBA Draft, they immediately traded him on draft night. Leonard led the Spurs to the 2014 NBA championship, cementing his transformation from elite 3-and-D player to a legitimate superstar. Unfortunately, things went sour in San Antonio.
The 2014 Finals MVP suffered a quadriceps injury. His availability was in question, especially when the Spurs' medical team gave the green light for him to play. Despite a quiet stance by Leonard, tensions quickly turned into turmoil within the organization, which caught the eye of Spurs legend himself David Robinson.
Interestingly, Leonard's uncle, Dennis, once again got involved. He threw fire into the heated situation, claiming that San Antonio's doctors had a lack of trust towards the injured superstar. Eventually, Leonard requested a trade, landing him in Toronto, where he won his second NBA title. While it was a bold and successful decision for Leonard, it was one of the ugliest exits by a superstar from his original team.
3. Kawhi Leonard's father was gunned down

One of the biggest moments of Leonard's life was the tragic passing of his father, Mark Leonard. Kawhi Leonard was only 16 years old, still with King High School, when he had a game to play in January 2008. The elder Leonard was expected to be in attendance to support his talented son. Unfortunately, Leonard's father couldn't make it.
Mark was reportedly gunned down in the family's car wash in Compton. Before the incident, Leonard's father was engaging with an old friend, who was dealing with a dispute. Shortly after the discussion, there was suspicious activity at the site before a gunman took action. To this day, the murder of Leonard's father remains a cold case as authorized figures have yet to identify the shooter.
It was a dramatic turn of events for Leonard. In fact, the King High School star even suited up for a game a day later. He scored 17 points in the 68-60 loss against Compton Dominguez. Leonard's father was reportedly also a huge figure in his life as a mentor and motivator.
2. Kawhi Leonard's sister gets sentenced to life in prison

Although Leonard has already proven himself to be a basketball superstar, winning two NBA championships with different franchises, that still doesn't guarantee a peaceful household. In fact, Leonard's sister Kimesha Williams was convicted of the murder of 84-year old citizen Afaf Assad.
At Pechanga Resort Casino, Williams along with her friend Candace Townsell connived for a robbery against Assad. The deed was done inside the bathroom, leaving Assad with a fractured skull. The incident forced judges to pronounce both Williams and Townsell guilty of first-degree murder and elder abuse.
1. $28 million Aspiration endorsement scandal

Currently, the biggest story in the NBA offseason is turning heads with Leonard at the center of the reveal. In a program called Pablo Torre Finds Out, it was revealed that Steve Ballmer, the owner of the Los Angeles Clippers, used his now-bankrupt fraudulent tree-planting firm Aspiration to pay the Clippers star $28 million. The move is seen as a way for the Clippers to pay Leonard more than his contract, a violation of league rules.
The situation seems serious, given that the NBA has already launched an investigation into the matter, hiring external law firm Wachtell, Lipton, Rosen & Katz. If enough evidence supports the claim, the Clippers will have to face serious repercussions. Interestingly, Leonard's endorsement deal with Aspiration was a “no-show job.”