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3. The Dave Littlefield Era (July 2001 - Sept. 2007)
Reggie Sanders (March 2003, 1 year, $1 million)
Littlefield found a bargain in Sanders, a veteran outfielder who averaged 3 WAR over his first 11 full seasons in the Majors. Injuries and strikeout numbers cooled the market for Sanders, allowing the Pirates to take a risk. Luckily, the gamble paid off with Sanders leading the club in homers (31) and finishing ninth in the NL in slugging percentage (.567). The Pirates let Sanders walk at the end of the season, which seemed questionable at the time given his success in 2003. The Cardinals signed Sanders to a two-year, $6 million deal in hopes that his powerful bat would pay off in St. Louis. However, Sanders never found the level of success he enjoyed during his sole season in Pittsburgh and ultimately contributed a mere 4.2 WAR over his final four seasons in baseball.