Kawhi Leonard could be costliest free agent in NBA history

Leonard reportedly agreed to an endorsement deal with Aspiration, a jersey sponsor for the Los Angeles Clippers, for $28M in compensation and $20M in stock, months after Clippers owner Steve Ballmer invested $50M in the company. If the NBA's investigation finds the Clippers used that deal to circumvent the salary cap, the team could be fined millions of dollars and have to forfeit at least one first-round pick. But that's only a small part of what Leonard has cost the Clippers since joining them as a free agent in 2019.

Kawhi Leonard signed deals with Clippers worth nearly $400M

When Leonard first joined the Clippers, he signed a three-year deal with a player option for $103.1M. Leonard declined that option in 2021 to sign a four-year contract worth $176.3M, then signed an extension in 2024 worth $149.5M over three seasons.

For all that money, Leonard has played 266 games in his six seasons in Los Angeles, an average of just over 44 games per season — out of 82. He did make three All-Star teams and three All-NBA teams, but the Clippers themselves have had limited postseason success. In the Leonard era, they've won three playoff series and lost five, advancing to the conference finals in 2021 after Leonard suffered a torn ACL in the second round.

L.A. missed the playoffs in 2022 and has lost in the first round in the last three seasons. Leonard played only two games in those first two series due to injuries.

The Los Angeles Clippers incurred extra costs to sign Kawhi Leonard 

To land Leonard in 2019, the superstar forward wanted the Clippers to add another star to play alongside him — and he wanted it to be Paul George. So the Clippers sent a massive haul of players and picks to the Oklahoma City Thunder to make it happen: Five first-round picks, one first-round pick swap, Danilo Gallinari and future MVP Shai Gilgeous-Alexander. One of those first-rounders became All-Star Jalen Williams, who averaged 23.6 points in the Thunder's NBA Finals win this year.

Not only did the Clippers miss out on two of the best young players in the NBA, but they also weren't able to enjoy the benefit of those young players' affordable contracts. Since the Clippers had to fill out their roster with more expensive veterans instead of first-round picks on rookie deals, their payrolls were very high in the Leonard era. That's how they ended up paying $371M in luxury tax since acquiring Leonard, including over $140M in both the 2022-23 and 2023-24 seasons.

When you consider salaries, taxes, talent and lost opportunities, Leonard was probably the costliest free-agent acquisition in NBA history even before this NBA investigation. All they got out of it was a team that usually loses in the first round of the playoffs — exactly what they had the season before he arrived.