2. Richard Jefferson, 2010: 4 years, $39M
Richard Jefferson had a Spurs tenure much like Gasol’s in that it seemed like an incredible move when San Antonio acquired him. The ESPN analyst (and former foe of the Silver and Black during the 2003 Finals) was coming off a career year with the Bucks and seemed like a seamless fit next to Timmy, Tony, and Manu. Needless to say, as his stats slipped in essentially every major category, Spurs fans were disappointed.
And much like with Gasol, the front office decided to double down on Jefferson, signing him to a substantial deal. The team invested in him during the summer of 2010, but by the following year, they were ready to spend the 15th overall pick in the draft on a young forward named Kawhi Leonard. San Antonio ultimately shipped RJ to Golden State at the trade deadline during Leonard's rookie season.