Twenty-eight million dollars — seven million a year — is an enormous amount of money, especially for a player who wasn’t actually required to do anything. Kawhi Leonard, one of the NBA’s biggest stars, is now at the center of an alleged scheme that may have been designed to bypass the league’s salary cap rules. While Leonard’s case is currently making headlines, he is far from the only player accused of financial misconduct. From Terrence Williams to Glenn “Big Baby” Davis, several former NBA players have become infamous for orchestrating or joining fraudulent financial schemes after their careers ended.

The controversy surrounding Leonard began on September 3, 2025, when investigative journalist Pablo Torre released a bombshell report revealing that Leonard had signed a $28 million, four-year endorsement deal in April 2022 with Aspiration — a Los Angeles–based “green bank” that promoted sustainability initiatives. What made the deal suspicious was that it appeared to function as a “no-show” job: Leonard was allegedly paid millions for doing nothing, allowing the Los Angeles Clippers to funnel him extra compensation outside his NBA contract, effectively skirting salary cap regulations.

According to Torre’s investigation, Clippers owner Steve Ballmer had invested $50 million in Aspiration through his personal LLC in 2021. Shortly afterward, the Clippers announced a $300 million partnership with Aspiration, including a sponsorship for their new Intuit Dome arena and a jersey patch deal. Documents obtained by Torre and testimony from former Aspiration employees suggested that Leonard’s endorsement deal — executed through his company KL2 Aspire LLC — was part of this broader financial network. The contract not only paid him $7 million annually but also included a clause that allowed him to decline any promotional activity while still collecting full payment. Even more suspicious, the deal automatically ended if Leonard left the Clippers or retired, directly tying the payout to his tenure with the team.

Torre found no evidence that Leonard did any marketing for Aspiration — no ads, no social media posts, no appearances. The only public connection came in a 2023 Clippers tweet wishing Leonard a happy birthday, promising that Aspiration would plant a tree for every retweet. For a $28 million endorsement, this single post was hardly convincing. A former Aspiration finance employee even told Torre’s podcast that they were informed internally the purpose of the deal was to “circumvent the salary cap.” The employee added that Leonard’s contract dwarfed other celebrity deals with the company, including those of Robert Downey Jr., Leonardo DiCaprio, and Drake, whose combined endorsements were worth less than a quarter of Leonard’s payout.

Aspiration later filed for Chapter 11 bankruptcy in March 2025, and its co-founder, Joseph Sanberg, pleaded guilty to defrauding investors and lenders of over $248 million. Bankruptcy filings showed that the Clippers were Aspiration’s largest creditor, owed $30 million, followed by Ballmer’s other company, Forum Entertainment, owed $11 million, and KL2 Aspire LLC, Leonard’s company, owed $7 million. Ballmer and the Clippers have denied any wrongdoing, claiming they too were victims of fraud. Ballmer insisted that his investment was made in good faith, motivated by environmental concerns, and emphasized that Leonard’s NBA extension — worth $176 million over four years — had already been signed before the Aspiration deal existed.

If Leonard’s case represents a potential salary cap manipulation, the next story shows outright criminal deception. Terrence Williams, a former 11th overall pick in the 2009 NBA Draft, once had a promising career playing for teams like the Nets, Rockets, and Celtics. But between 2017 and 2020, he masterminded one of the most audacious fraud schemes in NBA history — a plan that stole nearly $4 million from the NBA’s Health and Welfare Benefit Plan. Williams recruited other retired players, providing fake invoices from fake medical and dental offices to file claims for procedures that were never performed. He personally collected at least $230,000 in kickbacks from fellow players, including $30,000 from guard Will Bynum. Williams even impersonated a league health plan employee and threatened players who hesitated to pay him. In August 2023, he was sentenced to 10 years in prison and ordered to repay $2.5 million.

Among those Williams recruited was Glenn “Big Baby” Davis, a former NBA champion with the Boston Celtics. Davis had earned more than $32 million during his playing career but struggled financially after retirement, facing child support issues and failed investments. Seeking fast money, he joined Williams’ scheme, submitting fake dental claims — including one for crowns on eight teeth while he was actually out of state. He was sentenced in May 2024 to 40 months in prison and ordered to repay $80,000, marking a dramatic fall from grace for a former champion.

Will Bynum, another participant, was known for his grit and determination during his NBA career, earning about $22 million. Yet he too filed fake claims — including one for $182,000 at a fake chiropractic office — and paid Williams a $30,000 kickback. He was convicted of conspiracy to make false statements and sentenced to 18 months in prison.

Tony Allen, a six-time All-Defensive Team member and another 2008 Celtics champion, shocked fans by joining the same fraud ring. Known as “The Grindfather” for his defensive tenacity, Allen and his wife, Desiree, both faced charges. He ultimately pled guilty, cooperated with authorities, and received a lenient sentence of three years probation and community service, avoiding prison time — though his reputation was permanently tarnished.

Sebastian Telfair, once a high school prodigy expected to be the next great point guard, also fell into the same trap. Despite earning $19 million in his career, poor financial management led to hardship after retirement. He joined Williams’ scheme and was later sentenced for health care fraud. In 2025, he served six additional months for violating supervised release, showing that his legal troubles persisted even after conviction.

Finally, there’s Darius Miles — perhaps the most tragic example of all. A former high school sensation turned NBA star, Miles earned nearly $62 million during his nine-year career. Yet through reckless spending, poor investments, and lack of financial guidance, he lost everything and eventually declared bankruptcy. His downfall illustrates how even immense wealth can vanish without discipline and sound management.