1. Rasho Nesterovic, 2003: 6 years, $42M
If you reacted to this name with a resounding “Whaaaaat?!?,” know that you’re not alone. Signing Rasho to a $40M+ deal doesn’t feel very Spursian. Nesterovic was a decent player before landing in San Antonio, averaging career highs across the board as one of the best early 2000s Minnesota Timberwolves not named Kevin Garnett.
Signing him in an attempt to replace David Robinson (who retired following the 2003 Finals) was a logical investment. The Spurs giving him such a long commitment was curious. Rasho almost immediately turned into a bit of a pumpkin. Though he started every regular season contest during the 2005 championship season, he only played eight minutes per game in the playoffs. Two summers later, San Antonio traded Nesterovic to Toronto for Matt Bonner.
The list of worst free agent signings in Spurs history isn’t awful, especially considering moves other franchises have made over the years. You could write an article about poor decisions from every team across every sport. Building a winning organization can be a crapshoot, which is why San Antonio's sustained success is incredibly hard to come by.
My only hope is this piece will serve as a reminder to all that as the team approaches free agency, not every move will be perfect.