In recent years, the NBA has faced a series of shocking financial scandals involving former and even current players. From endorsement schemes designed to skirt salary cap rules to elaborate healthcare fraud operations, several athletes who once enjoyed fame and fortune have found themselves entangled in criminal investigations.

Kawhi Leonard and the Aspiration Scandal

The most recent controversy involves Los Angeles Clippers star Kawhi Leonard. On September 3, 2025, investigative journalist Pablo Torre published an explosive report alleging that Leonard’s $28 million endorsement deal with a Los Angeles-based green bank, Aspiration, was effectively a no-show job created to funnel extra income to him outside the NBA’s salary cap.

According to Torre’s investigation, Clippers owner Steve Ballmer invested $50 million into Aspiration through his private LLC just months before the Clippers signed a $300 million sponsorship agreement with the company. Later, Leonard signed a four-year, $28 million endorsement contract through his company, KL2 Aspire LLC — a deal that required no actual promotional work.

Even more suspicious, the contract reportedly ended if Leonard left the Clippers or retired, directly tying the payments to his presence on the team. Aspiration employees told Torre that the arrangement was intentionally designed to “circumvent the salary cap.”

Aspiration later filed for bankruptcy in March 2025, and its co-founder Joseph Sanberg pleaded guilty to wire fraud involving more than $248 million. Bankruptcy filings revealed that the Clippers were among the largest creditors, owed $30 million.

Both Ballmer and the Clippers have strongly denied any wrongdoing, claiming they were victims of Aspiration’s fraud. “They defrauded me,” Ballmer told ESPN’s Ramona Shelburne, insisting that his investment was made for environmental reasons, not to benefit Leonard financially.

Terrence Williams and the NBA Health Insurance Fraud

Former NBA player Terrence Williams orchestrated one of the most audacious fraud schemes in league history. Between 2017 and 2020, Williams led a criminal enterprise that defrauded the NBA’s Health and Welfare Benefit Plan of nearly $4 million. He recruited other former players, provided fake medical invoices, and even impersonated a health plan employee to carry out the scam.

Williams personally received about $230,000 in kickbacks from ten players, including Will Bynum. In 2023, he was sentenced to ten years in prison and ordered to pay $2.5 million in restitution.

Glenn “Big Baby” Davis

Once an NBA champion with the Boston Celtics, Glenn Davis was also caught in the same healthcare fraud scheme. Despite earning over $32 million during his career, Davis faced financial struggles after retirement. Prosecutors proved that Davis submitted fake dental claims while he was in another state, including for the same teeth as other players.

In May 2024, Davis was sentenced to 40 months in prison and ordered to pay $80,000 in restitution — a stunning fall for a former champion.

Will Bynum

Will Bynum, known for his grit during his time with the Detroit Pistons, was also implicated. He filed a false claim worth $182,000 and paid Williams a $30,000 kickback. Bynum was convicted of conspiracy to make false statements and sentenced to 18 months in prison.

Tony Allen

Perhaps the most shocking name linked to the fraud was Tony Allen, a six-time NBA All-Defensive Team member and 2008 champion. Allen and his wife, Desiree, were both charged in the healthcare scheme. However, Allen cooperated with authorities and pleaded guilty, earning a lenient sentence of three years’ probation and community service. Still, the scandal permanently damaged his reputation as one of the league’s most respected defenders.

Sebastian Telfair

Sebastian Telfair, once a high school basketball prodigy, also joined the fraudulent operation. After earning $19 million during his NBA career, financial struggles led him to participate in Williams’s scheme. Although he denied wrongdoing, he was convicted and later violated his supervised release, serving six additional months in prison in 2025.

Darius Miles

Darius Miles’s story might be the most tragic. Drafted straight out of high school, he earned nearly $62 million over his NBA career but declared bankruptcy after years of reckless spending and poor investments. Reports suggest Miles also became entangled in fraudulent activities in a desperate attempt to recover financially. His downfall serves as a grim reminder of how quickly fortune can disappear when mismanaged.

The Bigger Picture

These cases reveal a troubling pattern among professional athletes who fail to manage their wealth responsibly after retirement. The combination of immense early earnings, limited financial education, and the pressure to maintain a lavish lifestyle often leads to disastrous consequences. From Kawhi Leonard’s alleged endorsement scheme to Terrence Williams’s organized fraud network, the stories serve as cautionary tales of how greed and poor judgment can destroy both fortunes and legacies.