Shocking: NBA has hired a “super lawyer” to get involved

The NBA has officially retained prominent New York-based law firm Wachtell, Lipton, Rosen & Katz to investigate claims that Los Angeles Clippers star Kawhi Leonard was involved in an endorsement deal designed to circumvent the league’s salary cap. The high-stakes investigation, prompted by recent revelations and whistleblower claims, raises serious questions about the integrity of financial dealings between Leonard, the Clippers, and the now-bankrupt green banking company Aspiration.

This latest move by the league signals a shift toward a more serious and formal examination of alleged misconduct — and could result in historic consequences for one of the NBA’s richest owners, Steve Ballmer, as well as the franchise he owns.

The Origins of the Investigation: A “No-Show” Endorsement Deal Worth $28 Million

The controversy began with the disclosure that Kawhi Leonard signed a $28 million endorsement deal in 2022 with Aspiration, a San Francisco-based environmentally focused financial firm. The agreement was supposed to span four years, but internal reports and whistleblower claims — first aired on the Pablo Torre Finds Out podcast — described the deal as a “no-show job”.

Aspiration insiders alleged that Leonard did little to no promotional work, and The Athletic later revealed that the contract included a clause allowing Leonard to refuse any promotional requests made by the company. This effectively allowed Leonard to be paid millions without performing any tangible work or promotional appearances for Aspiration — an arrangement that, if linked to the Clippers, could be viewed as a covert form of compensation beyond the salary cap.

The $20 Million Side Deal: Undisclosed Stock from a Fraudulent Co-Founder

Further complicating the matter is the claim that Leonard was also offered a separate deal valued at approximately $20 million in stock, reportedly from Aspiration co-founder Joe Sanberg’s personal holdings. This brings the total value of the endorsement to $48 million, a figure that has stunned both league observers and legal analysts.

Sanberg has since agreed to plead guilty to defrauding investors of $248 million, further damaging the legitimacy of the company and shedding light on potentially deceptive financial practices involving NBA players.

Why Wachtell, Lipton, Rosen & Katz Is Leading the Case

The NBA’s decision to hire Wachtell Lipton indicates the seriousness of the investigation. The firm has a notable track record in handling sensitive league matters, including:

• The Donald Sterling scandal in 2014, where the former Clippers owner was banned for life over racially insensitive comments.

• The Robert Sarver case in 2022, which led to the Phoenix Suns owner being suspended and ultimately selling the franchise.

Wachtell Lipton’s involvement often precedes major disciplinary actions. The firm doesn’t just audit facts — it builds cases, presents findings to the league, and influences executive decisions on penalties and ownership changes.

Steve Ballmer’s Investment and Potential Conflict of Interest

Ballmer, who is worth $153 billion according to Forbes, invested $50 million into Aspiration in 2021. The company was later announced as the Clippers’ official jersey and arena sponsor, a deal valued at $300 million over 23 years. While Ballmer has publicly denied knowledge of Leonard’s endorsement deal, he did admit to introducing Leonard to Aspiration executives — a connection that could prove problematic.

If investigators determine that Ballmer’s investment was strategically aligned with Leonard’s deal to keep his salary artificially low and avoid cap limitations, the repercussions could be significant. This would constitute a direct breach of the NBA’s Collective Bargaining Agreement (CBA), specifically under rules regarding salary cap circumvention.

Leonard’s Contract Flexibility Raises Questions

In January 2024, Kawhi Leonard signed a three-year extension with the Clippers worth $153 million — notably not a max contract. This team-friendly deal gave the Clippers greater roster flexibility, but it also drew attention. Some rival executives questioned why a player of Leonard’s caliber would take less than the maximum amount unless compensated elsewhere — a theory that ties back into the allegations surrounding Aspiration.

NBA’s Penalties for Salary Cap Violations: What Could Happen?

If the NBA investigation confirms a salary cap circumvention, the league has broad authority to impose severe penalties under Article XIII, Section 3 of the CBA. These could include:

• A fine of up to $7.5 million for the team.

• Direct forfeiture of draft picks.

• Voiding Leonard’s contract, or any amendments or extensions made under suspicious circumstances.

• A fine of up to $350,000 for Leonard himself.

• A suspension of up to one year for any team personnel found to be willfully involved.

• Voiding the transaction or agreement that violated league rules and requiring the return of any funds received, unless the player can prove he was unaware of the violation.

The Clippers have already been penalized in the past for similar infractions. In 2015, the team was fined $250,000 for offering free agent DeAndre Jordan an unauthorized endorsement opportunity. Given this prior offense, any new penalties could be even more severe.

Aspiration’s Collapse and Bankruptcy Fallout

Aspiration has since filed for bankruptcy amid revelations of financial fraud. According to filings, the Clippers and Ballmer-owned Forum Entertainment are the two largest creditors, followed by Leonard’s KL2 Aspire LLC, which is owed $7 million.

The company’s demise further fuels suspicions. Not only did it fail to deliver promised services to Leonard, but the fraudulent activities of its co-founder Sanberg — who promised stock worth millions — may have been used as tools in circumventing NBA compensation limits.

NBA’s Broader Interest in Preserving Integrity

The NBA’s swift hiring of Wachtell Lipton also serves a larger purpose: protecting the integrity of the salary cap system. The league has worked hard to build parity and ensure that no team, regardless of financial backing, can manipulate the system to build unfair advantages.

If the allegations prove true, the Clippers’ arrangement with Leonard and Aspiration would strike at the very core of that system. It would suggest that off-the-books compensation — through outside investments, sham endorsements, or fraudulent partnerships — could be used to sidestep financial restrictions placed on teams.

What Comes Next?

As of now, the investigation is ongoing. While no formal charges or penalties have been announced, the involvement of one of the NBA’s top legal firms suggests that the league is preparing for the possibility of disciplinary action.

Leonard, Ballmer, and the Clippers organization have all denied any wrongdoing, maintaining that all transactions were legitimate and independent. However, the legal consequences will hinge on whether the league finds a direct or indirect connection between Ballmer’s investment, Leonard’s endorsement, and the Clippers’ strategic interests.

With Wachtell Lipton leading the inquiry, and the league’s internal legal office assisting, the NBA is preparing a thorough review. Whether that results in fines, suspensions, or more drastic measures like voiding contracts or losing draft picks, will depend on what the investigators uncover — and how the league chooses to respond.

Final Thoughts

This case is more than just another headline — it could set a precedent for how off-court deals, sponsorships, and ownership investments are scrutinized in the future. With $48 million in alleged outside compensation, a $50 million owner investment, and a team already under prior sanctions, the Kawhi Leonard–Clippers saga may become one of the most impactful financial investigations in modern NBA history.

The league’s final decision could reshape how superstars and franchises conduct business — and just how far teams can go in pursuit of competitive advantage.