5. Spurs trade Bruce Bowen, Fabricio Oberto, Kurt Thomas for Richard Jefferson (2009)
On paper, this deal didn’t seem horrible for the Spurs at the time. While Bruce Bowen was pivotal in San Antonio’s three championships since 2003, he had just turned 37 and was on the last legs of his career. Fabricio Oberto’s minutes had significantly reduced from the two seasons prior, while Kurt Thomas was a plug-and-play forward that could easily be replaced.
Meanwhile, Richard Jefferson was coming off a season in Milwaukee in which he averaged 19.6 points and 4.6 rebounds per game, marking the fifth time he’d averaged over 18 points per game in a season.
Jefferson was 29 years old at the time, so it would make sense that he had plenty to offer the Spurs as a complimentary piece to the Big Three. Unfortunately, the 2008-09 season marked the last time Richard scored more than 12.3 points per game in a season, as his offensive decline seemed to hit earlier than expected.
R.J. never seemed to mesh well with Gregg Popovich, seeming to lack effort even in crucial playoff situations. As a result, the Spurs traded Jefferson in 2012 for a familiar face in Stephen Jackson, who ended up having his own issues upon returning to San Antonio.
Next: No. 4