Despite Kawhi Leonard being 8 years older, more injury prone, and having an integral role in a cap circumvention scandal, the Toronto Raptors gave up more to acquire him from LA than they did to acquire him from San Antonio in 2018
Toronto received: Kawhi Leonard, Danny Green
San Antonio received: DeMar DeRozan, Jakob Pöltl and a protected 2019 FRP (conveyed and became Keldon Johnson)
Toronto received: Kawhi Leonard
Clippers received: Brandon Ingram, Gradey Duck, 2031 and 2033 unprotected FRPs, a 2027 FRP swap, 2030 and 2033 2RPs
It should also be noted that Kawhi exerted pressure via an expiring contract both times to steer his way to his preferred team (unsuccessfully, and then successfully in 2026)