3. Rudy Gay
The Spurs were coming off a trip to the Western Conference Finals when they signed Gay in 2017. Kawhi Leonard was a superstar, and LaMarcus Aldridge was an All-Star. San Antonio still had Tony Parker and Manu Ginobili, but they were past their primes. The Spurs figured to be a contender, so Rudy Gay took less money to join them in hopes of chasing a title.
The 6’8 forward was coming off an Achilles injury, but he was healthy enough to start the season. Kawhi Leonard was not, and his quad issue limited him to just nine games. Gay suffered a heel injury that only allowed him to play 57 games as San Antonio won 14 fewer and was bounced in the first round of the playoffs by the Golden State Warriors.
Gay was not the same player. He consistently averaged 18 points per game before the injuries and was playing 35 minutes per game. The 6’8 forward averaged just 23.0 a night in San Antonio as he came off the bench. Gay could still get a bucket, but he was no longer as dynamic.
The San Antonio Spurs kept him for four years, despite going from contender to rebuilder. Rudy Gay departed in free agency in 2021, but it was years too late for the franchise, especially after they gave him a second contract in 2019 that paid $14-plus million per year.