Giles was without a doubt one of the most feared hitters in baseball from 1999 up until the point when he was dealt to the Padres. During this stretch he hit 35 or more home runs each season, while recording a batting average just above .300.
What made the move so puzzling, though, was the fact that San Diego was not in playoff contention. To add to the confusion, they traded away some of their top prospects in Jason Bay and Oliver Perez in order to acquire Giles.
Bay would win Rookie of the Year honors the following season, and would go on to be a two-time All-Star in Pittsburgh. Unfortunately, his talents were wasted playing for a team that was in the midst of a two-decade playoff drought, and he was traded to the Boston Red Sox in 2008.
Perez would experience a very successful 2004 campaign with the Pirates, recording a 2.98 ERA while averaging 11 strikeouts per nine innings. Aside from that season he has struggled for the majority of his MLB career – though he has been a reliable pitcher for the Seattle Mariners and Arizona Diamondbacks for the past few seasons after making a move to the bullpen in 2012.
While Giles never returned to the All-Star status he achieved with the Pirates, he was a reliable hitter that played a vital role in the Padres winning the National League West in 2005 and 2006. He would spend the final six seasons of his career with the team, and retired as one of the most beloved San Diego sports figures of the 2000s.
The third player sent to Pittsburgh in the deal, a left-handed pitcher named Cory Stewart, would never reach the majors.
While none of the players or teams involved in this trade would experience overwhelming success following the trade, it was a move that netted the Pirates a Rookie of the Year and helped the Padres return to the playoffs.
Next: Phillies acquire Matt Stairs