An “Aspirational” Endorsement Deal Raises Eyebrows

In a bombshell revelation on September 3, 2025, investigative reporter Pablo Torre alleged that the Los Angeles Clippers and Kawhi Leonard may have orchestrated a $28 million “no‑show” endorsement agreement with a now‑bankrupt entity, Aspiration, Inc., a purported tree‑planting firm. The deal, structured via Leonard’s own LLC (KL2 Aspire LLC), reportedly entailed $7 million annually from 2022 to 2025, despite there being no public promotion or endorsement activity by Leonard, and a termination clause tied to his Clippers status.

Interestingly enough, Clippers owner Steve Ballmer financially backed Aspiration with $50 million, suggesting a potential avenue to funnel compensation outside the NBA’s salary cap framework. To get a better understanding of what’s going on, first we have to understand what an endorsement deal is.

An endorsement deal is a type of agreement where a company pays an athlete, entertainer, or other public figure to promote its products or services. In return, the individual allows the company to use their name, image, likeness, or reputation in advertising, marketing, or product placement.

These deals can involve things like appearing in commercials, posting on social media, wearing branded gear, or making public appearances on behalf of the brand. At their core, endorsement agreements are about leveraging the credibility and popularity of the individual to boost consumer trust and sales for the company.

What Do Typical Endorsement Deals Look Like?

• Performance & Exposure Based: Customarily, athlete-brand contracts tie compensation to promotional activities i.e. appearances, ads, social media, event participation, and use of name/image. The athlete is contractually obligated to endorse publicly and positively.

  
  

• Fair Market Value Evaluation: Brands pay rates proportional to an athlete’s visibility, draw, and performance metrics. Agencies bargain based on expected ROI and media reach.

  
  

• Compliance with League Rules: In the NBA, the league must be notified of significant third-party deals, and compensation exceeding market value (or contingent upon on-court decisions) risks violating tampering or cap‑circumvention rules.

  
  

How Does Kawhi’s Deal Differ?

• No Deliverables: Reports suggest Leonard didn’t promote Aspiration, likely not doing interviews, ads, or appearances.

  
  

• Back‑door Financing: Ballmer’s injection into Aspiration appears timed to give a compensation vehicle disconnected from the NBA's official salary structure.

  
  

• In‑League Ties: The deal tied its continuation to Leonard’s tenure with the Clippers, raising alarms for dependency upon team association.

  
  

• Fake or Inflated Contracts: The endorsement seems disconnected from typical branding functions, instead serving as a workaround for cap limitations.

  
  

What Should One Watch For in Endorsement Deals (Especially Athlete/Team Linked)?

• Tangible Deliverables: Any deal should include clear duties: media appearances, social media, photoshoots, public appearances, brand usage, or community events.

  
  

• Market Value Calibration: Compensation must reflect industry standards, not inflated to mask cap circumvention. Contracts should be reviewed by independent valuation experts when in doubt.

  
  

• Disclosure and Oversight: League offices, union representatives, and possibly third-party compliance audits should verify that the deal isn’t lurking outside official salary compliance

  
  

• Term and Termination Clarity: Watch for clauses that terminate when the athlete leaves the team, raising concerns about conditional compensation tied to roster status rather than performance or branding value.

  
  

• Independence from Ownership Structures: Deals structured via companies funded or controlled by team owners should raise immediate suspicion due to conflicts and potential for foul‑play.

  
  

Red Flags to Signal Caution or Investigation

• “No‑Show” Clauses: Payment without performance or public promotion.

  
  

• Back‑door Funnel via Shell Companies: Funds routed through obscure LLCs without transparency.

  
  

• Owner‑Controlled Sponsorship Shells: If the owner or entity tied to the team finances the brand or endorsement company, that’s a glaring conflict.

  
  

• Termination Link to Player’s Team Status: Raises questions of conditional compliance.

  
  

• Bankruptcy or Legal Fallout: If the endorsement partner faces legal or financial collapse, it may expose deeper issues.

  
  

Historical Parallel: The Timberwolves–Joe Smith Case

The Clippers’ situation echoes one of the most infamous salary‑cap circumvention cases in NBA history. In 2000, the Minnesota Timberwolves were discovered to have a secret agreement with forward Joe Smith. The deal promised Smith below‑market contracts for several years in exchange for a lucrative long‑term contract later, circumventing the NBA’s salary cap. Once exposed, the NBA levied one of the harshest penalties in league history: a $3.5 million fine and the forfeiture of five first‑round draft picks. Smith’s contract was voided, and the scandal remains a cautionary tale about hidden compensation mechanisms.

The alleged Kawhi‑Clippers endorsement arrangement differs in its structure. The money flows through a third‑party company rather than a direct player‑team promise, but the underlying principle is similar: the use of off‑books or artificial arrangements to deliver compensation beyond what the salary cap allows. For lawyers, agents, and compliance professionals, both cases highlight the vital importance of transparency and adherence to league rules when structuring deals that may overlap with player salaries.

If Torre’s report holds, the $28 million “endorsement” with Aspiration appears less like a legitimate branding campaign and more like a salary-cap end‑run disguised as a marketing deal. For sports‑law practitioners, it underscores why rigorous review and transparency are essential in endorsement contract design, especially when the contracting entity is tied to team ownership.

This debacle can serve as a cautionary case: endorsement contracts must reflect actual promotional work, be clearly separate from team compensation, and withstand scrutiny both from league compliance and public ethics standards. It’s the only way that the integrity of athlete branding, and league financial fairness can be preserved.

Stephon Burton is a DC and PA licensed attorney with Sneakers & Streetwear Legal Services, a Business and Intellectual Property law firm focusing on Fashion, Sports, and Entertainment. He can be contacted on LinkedIn and X (formerly Twitter).