Dave Littlefield

David Michael Littlefield (born June 16, 1960) is an American former Major League Baseball executive, who is currently a scout for the Detroit Tigers.

In 1984, Littlefield was an assistant coach for the Orleans Cardinals of the Cape Cod Baseball League.

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.

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.

The most notable examples of this were in 2002 and 2007.

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".

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."

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

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.

Littlefield's other #1 draft picks were Paul Maholm (2003), Neil Walker (2004), Andrew McCutchen (2005), and Brad Lincoln (2006).

Lincoln was drafted two picks before now superstar pitcher Clayton Kershaw was drafted by Los Angeles

Under Littlefield's direction, the Pirates were less aggressive than other teams in signing players from Latin America.

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.

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.

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.

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.

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.

On July 31, 2007, Littlefield traded outfielder Rajai Davis to the San Francisco Giants for pitcher Matt Morris.

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.

Though he was frequently criticized for some trades that worked out poorly in the long run, Littlefield also managed to acquire the bulk of the Pirates' lineup through trades during his tenure.

Jason Bay, Freddy Sanchez, Adam LaRoche, José Bautista, and Xavier Nady were all acquired through trades.

In his final season as GM, only one of the seven players with over 400 at-bats on the team, Ronny Paulino, was not acquired through a trade.

At the same time, this group finished in last place in their division, so even his more successful trades weren't enough to field a contender.

During Littlefield's tenure, the Pirates were widely criticized for taking players that were perceived to be more signable than talented.

In 2007, Littlefield and the Pirates passed over the top-ranked college hitting prospect, Matt Wieters, and instead drafted pitcher Daniel Moskos.

The move was widely criticized, as Morris, who was 7–7 with a 4.35 ERA at the time of the trade, was slated to make $9.5 million in 2008.

After battling with injuries, Bullington was waived by the Pirates in 2008.

Moskos had an inconsistent career in the minors (only playing in the MLB for the 2011 season), while Wieters was a four-time All-Star and two-time Gold Glove Award winner who would play in the MLB for 12 seasons.