4.) LaMarcus Aldridge 2015 Contract
We mentioned Aldridge earlier on this list, and this contract was the one that brought him to San Antonio. The Spurs lured LaMarcus away from the Portland Trail Blazers and signed him to a four-year deal worth $84 million during the 2015 offseason, pairing him with Kawhi Leonard.
Aldridge failed to live up to expectations at the beginning of this contract, scoring less than 20 points per game for the first time in five seasons. But he picked up his performance as he settled into the system, making two All-Star appearances and carrying the Spurs to the playoffs to keep their historic postseason streak alive.
3.) Kawhi Leonard 2015 Contract
Kawhi Leonard provided so much value for the Spurs during the life of his rookie-scale contract, helping them win their fifth championship in 2014. Following his ascension into superstar status, Kawhi re-signed with San Antonio on a five-year contract worth $94 million.
We know how this scenario played out, but if we put aside our disdain for a second, Kawhi had some excellent seasons during this deal. He was a two-time All-Star, averaged 25.5 points per game in 2017, and gained a reputation as a menace on the defensive end, earning the nickname "The Claw."
With all those positives came a lot of negatives. From publicly squabbling with Coach Popovich to the disastrous quadriceps injury, Spurs fans had a sour taste in their mouth when Leonard finally found a new home in the NBA.