2. Dante Cunningham
Dante Cunningham's time in San Antonio was a confounding one. The 6'8 small-forward journeyman found his way to the Spurs late in his career where he inexplicably became the team's starting power forward for 21 games.
Journeymen are journeymen for a reason, and Cunningham didn't provide enough on either side of the ball to warrant starting. After all, despite his size and length, he wasn't a good defender and while he shot 46.2% on threes on a limited number of attempts, he always seemed hesitant to take wide-open shots.
To think he started over former Spur Davis Bertans, who at least had an elite skill, is still hard to believe and makes no sense in retrospect. Luckily, Cunningham eventually fell out of the rotation and wasn't re-signed, which makes San Antonio the last stop in his NBA career.
1. Joffrey Lauvergne
The Spurs quickly scooped up power forward Joffrey Lauvergne in free agency after the Thunder opted not to extend him a qualifying offer. In hindsight, that probably should've been a red flag for San Antonio.
Initially, Lavergne seemed to be a decent signing at least, considering that he was a stretch four who could also finish around the basket. However, he wasn't actually a good 3-point shooter and stopped taking them with the Spurs.
Inexplicably, Lavergne was shoehorned into the role of backup center despite being a non-factor as a rim protector and an average rebounder. He also didn't impress on the offensive end where he struggled at times to finish, in addition to not actually spacing the floor.
It didn't take very long for him to lose his spot in the rotation, which proved to be the right decision. The Spurs would ultimately win 47 games and make the playoffs without much help from Lavergne. In the offseason, Lavergne declined his player option to return to the Spurs in favor of playing overseas and hasn't played in the NBA since.
All in all, San Antonio has definitely had some missteps in recent seasons when it comes to rotation players. They can't all be winners, I guess. But at least with the rebuild, San Antonio will likely rely less on free agency retreads and more on younger players who have the potential to exceed the players on this list. Thus, San Antonio probably won't make the same mistake twice, which bodes well for the future.