6. San Antonio Spurs trade Derek Anderson, Steve Kerr for Steve Smith (2001)
Derek Anderson was an outstanding player that was hampered by unfortunate injuries throughout his career. Coming out of Kentucky with an NCAA championship under his belt, Anderson had the total package on the court: solid defense, slashing ability, and shooting.
After decent seasons on some losing teams, Anderson took a discounted rate to become part of a winning culture in San Antonio. His addition went as well as anyone could hope, as he shot a career-high 39.9 percent from the outside to average 15.5 points per game.
As the Spurs’ second-leading scorer, Anderson played a crucial role in securing a 58-24 record and momentum going into the playoffs. Unfortunately, a cheap shot by Juwan Howard in the second round sidelined Anderson for the rest of the postseason, effectively ending the Spurs’ title hopes.
Making matters worse, talks fell through between Anderson and the Spurs front office in terms of getting him the deal he earned once the summer came around. As a result, the team had no choice but to ship him and Steve Kerr off to the Portland Trail Blazers in exchange for Steve Smith.
Smith was certainly no slouch, but by the time he made his way to the Alamo City, his best days were behind him. The Hawks version of Smith certainly would’ve made the trade worth it, but his two seasons were ho-hum compared to what the Spurs could’ve gotten from a 27-year-old Derek Anderson just hitting his stride.
Failed negotiations may have forced the trade, but how everything went down is still regrettable.
Next: No. 5