Littlefield has acquired a reputation throughout MLB as a difficult trading partner, in that his demands during negotiations are often seen as grossly excessive.

 Littlefield has traded 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 has repeatedly asked for lower-ceiling "major league ready" prospects in return. As a result, the Pirates have a plethora of mid-to-late 20's, 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.

 Even his most successful trade was of a somewhat dubious nature. In 2003, Littlefield approached the San Diego Padres with a trade proposal in which the Pirates would receive Xavier Nady, Oliver Perez, 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.[3] 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. Unfortunately for the Pirates, in order to do so he had to surrender struggling star pitcher Oliver Perez, who has become a better pitcher for New York, as well as veteran reliever Roberto Hernandez and the compensatory draft pick the Mets received when Hernandez left as a free agent that offseason.

 Among his worst 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 of 2002. Herges was promptly released in spring training, while Young has developed into one of the best young pitchers in baseball. Similarly, the 21-year-old Leo Nunez was traded to Kansas City in December of 2004; in return, the Pirates received 39-year-old Benito Santiago. Nunez was used as a reliever in 2005 and 2006, and in 2007 has emerged as one of Kansas City's most promising starters; Santiago had 6 hits with the Pirates before being released one month into the 2005 season. The inability to obtain significant returns on trades has been a staple of the Dave Littlefield era, and a key reason why the franchise has lost for 15 consecutive years.

 On July 31, 2007, Littlefield made one of the most confounding trades in baseball history. He traded outfielder Rajai Davis to the San Francisco Giants for pitcher Matt Morris. The move has been widely criticized, as Morris, who was 7-7 with a 4.35 ERA at the time of the trade, is slated to make $9.5 million in 2008. Many were surprised that the Pirates would take on such a large contract (especially without having the Giants pick up part of it), as their 2007 Opening Day payroll was just $38.5 million. At the time of the trade, the Pirates were 42-62, 14.5 games out of first place.