14. Stephen Jackson
Jackson was a second-round pick by the Suns in 1997, but he was waived after just four months. The 6’8 forward headed overseas for three seasons before finally getting a chance in the NBA with the Nets.
The 22-year-old immediately jumped into the rotation as he averaged 8.2 points, 2.7 rebounds, and 1.1 steals in 21.6 minutes per game as a rookie. After a third straight losing season, the Nets made massive changes, including trading for Jason Kidd and letting Jackson walk in free agency.
The 6’8 forward returned to Texas and signed with the Spurs where his career took off. Jackson struggled with injuries in his first season before playing a key role on San Antonio’s title team in 2003. He averaged over 33 minutes per game in the playoffs and made multiple clutch shots to propel the Spurs. San Antonio defeated the Nets in the 2003 NBA Finals, and Jackson got the last laugh over his former team.
Jackson left after just two years, and he bounced around the league for the remainder of his 14-year NBA career. Over the next eight seasons, Jackson averaged 18.5 points, 4.4 rebounds, 3.7 assists, and 1.4 steals in 36.8 minutes per game.
The Nets likely do not regret letting Stephen Jackson walk as they reached the NBA Finals two straight years after his departure, but it was a massive front office blunder, especially after he helped the Spurs defeat them in the 2003 NBA Finals.