Image Credit: Ron Chenoy-Imagn Images

Kawhi Leonard Sought Ownership Stake, Private Jet and Endorsement Deals Before Joining LA Clippers in 2019

Unusual demands shaped Kawhi Leonard’s 2019 decision

Image Credit: Ron Chenoy-Imagn Images

After winning the 2019 NBA Finals with the Toronto Raptors, Kawhi Leonard entered unrestricted free agency. His market quickly became a three-team race between the Raptors, Los Angeles Lakers, and LA Clippers.

Kawhi Leonard ultimately chose the Clippers, who traded Shai Gilgeous-Alexander to the Oklahoma City Thunder to acquire Paul George, fulfilling Leonard’s request to team up in Los Angeles. But according to reports, Paul George was not the only condition on the table.

ESPN’s Baxter Holmes reported that Kawhi Leonard and his uncle, Dennis Robertson, presented a list of unusual requests to the LA Clippers before his signing. These demands reportedly included part ownership of the franchise, a private plane, a house, and guaranteed off-court endorsement money.

Holmes noted that similar requests were made to the Raptors and Lakers. The Athletic had also reported in 2019 that Robertson pressed both teams with the same demands, even though such terms were outside the NBA’s collective bargaining agreement.

Potential Penalties for Clippers and Kawhi Leonard in Circumvention Case

—Leonard punishments:
• Void his contract and prohibit him from re-signing with the Clippers

• Require him to return the money he received from Aspiration

• Fine up to $350,000

— Clippers/Personnel… pic.twitter.com/bUt4znnbXG
— NBACentral (@TheDunkCentral) September 16, 2025

Lakers and Raptors Raised Concerns to the NBA

While neither the Raptors nor the Lakers entertained the unusual asks, both organizations expressed frustration to the NBA following the free agency cycle. The LA Clippers, however, reportedly agreed to some of the conditions, though not all, in their pursuit of Kawhi Leonard.

Those decisions have since come under scrutiny, particularly with renewed attention around Leonard’s ties to endorsement deals now being investigated by the league.

Old Reports Resurface Amid Ongoing Kawhi Leonard Scrutiny

Though Holmes’ report does not reveal entirely new information, it reaffirms details first shared in 2019 by The Athletic’s Sam Amick. At the time, Leonard’s demands were already a subject of league-wide discussion.

Now, with the NBA examining aspects of Kawhi Leonard’s financial dealings, those 2019 negotiations have returned to focus. This could further impact how the league penalizes the parties involved in the deal.