David Michael Littlefield (born June 16, 1960) is a former Major League Baseball executive, who is currently a scout for the Detroit Tigers. 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. He took over as GM for Roy Smith, who had assumed the position on a temporary basis after the firing of GM Cam Bonifay on June 11.
Early years
In 1984, Littlefield was an assistant coach for the Orleans Cardinals of the Cape Cod Baseball League.
Pittsburgh Pirates
2003 Rule 5 draft
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. The Cincinnati Reds, picking seventh, had all five Pirate players listed on their draft board and were frustrated to see them all go too soon, and an anonymous executive from another American League team said that his team had also planned to take a Pirate prospect, refraining only because in his words, "There wasn't anything left."
Trading record
Littlefield acquired a reputation throughout MLB as a difficult trading partner, in that his demands during negotiations were often seen as grossly excessive. It was rumored that Littlefield turned down a trade offer in 2005 with former GM of the Philadelphia Phillies, Ed Wade, in which the Pirates would swap pitcher Kip Wells for the Phillies' Ryan Howard. There were also unconfirmed reports that Littlefield turned down trading Howard for pitcher Kris Benson a year earlier.
Littlefield was criticized for trading players such as Jason Schmidt, Jason Kendall, Sean Casey, Aramis Ramírez, Chris Young, Gary Matthews, Jr., and Kenny Lofton for little or nothing in return. 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. As a result, when he left, the Pirates had a plethora of mid-to-late 20s, borderline Major Leaguers, and very few young, impact prospects within the system. This strategy runs contrary to that of successful low-payroll teams like the A's, Twins, and Marlins.
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. The Padres refused to surrender Nady, so Littlefield and the Pirates agreed to accept Jason Bay instead. 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. Two years later, Littlefield was successful in trading for Nady in a deal for inconsistent pitcher Óliver Pérez as well as veteran reliever, and soon to be free agent, Roberto Hernández and the compensatory draft pick the Mets received when Hernández left as a free agent that offseason.
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. Herges was promptly released in spring training, while Young was hailed as one of the best young pitchers in baseball four years later after having been traded from the Montreal Expos to the Texas Rangers and, finally, to the San Diego Padres, where he had an outstanding season in 2007 then struggled afterward. 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. Núñez has had some successful stretches for the Royals; Santiago had 6 hits with the Pirates before being released one month into the 2005 season. Some argue trading away future impact players has severely hindered the Pirates in recent years.