[1] Previously, Littlefield was employed as senior vice president and general manager of the Pittsburgh Pirates, a position he held from July 13, 2001, to September 7, 2007.
[2] Littlefield received a large amount of negative publicity after the Pirates lost five prospects from their minor league system with the first six picks in the 2003 Rule 5 draft, even though they had unused spots on their 40-man roster and could have protected several of the players if they had chosen to do so.
Chris Shelton, who had recently been honored as the team's minor league player of the year, went with the first pick, and he was followed in short order by Rich Thompson, Frank Brooks, Jeff Bennett, and José Bautista.
[citation needed] While small market teams thrive on trading established veterans for packages of talented minor leaguers, Littlefield repeatedly asked for lower-ceiling "Major League ready" prospects in return.
[7][8] In 2003, Littlefield approached the San Diego Padres with a trade proposal in which the Pirates would receive Xavier Nady, Óliver Pérez, and minor league pitcher Cory Stewart in exchange for star outfielder Brian Giles.
[9] Bay immediately emerged as a star, winning the National League Rookie of the Year award in 2004, while Nady spent the next three seasons as a part-time player with the Padres and the New York Mets.
Among his most widely lampooned transactions to date was the trade of pitcher Chris Young, in whom the Pirates had invested $1.5 million, to Montreal for Matt Herges in December 2002.
Similarly, the 21-year-old Leo Núñez was traded to Kansas City in December 2004; in return, the Pirates received 39-year-old Benito Santiago in order to fill an immediate hole at the catcher position.
In 2002, the Pirates passed over Melvin Upton, Jr., widely regarded as the top prospect at the time, with the first overall pick—also passing over other highly touted prospects, including Prince Fielder, Zack Greinke, Khalil Greene, Scott Kazmir, Nick Swisher, Matt Cain, Cole Hamels and Jeff Francoeur—and drafted Bryan Bullington, who Littlefield said could be a "good #3 pitcher".
The Pirates were widely criticized for failing to employ a Latin American scouting director until hiring Rene Gayo nearly three years after Littlefield took over as general manager.
Some contend (particularly beat writer Dejan Kovacevic) that, as much as any other decision during Littlefield's tenure, the lack of emphasis on competing in Latin America was one of the most confounding and debilitating for the organization.