The recent release of Matt Morris from the Pirates, forcing the team to eat about $11 M in the process, puts an end to the Dave Littlefield era of horrible roster moves.  As a Pirates fan, I celebrated last fall when Littlefield received the axe, relieving the Pirates from his 5+ years of horrible leadership.

While I don't believe in celebrating when people lose their jobs, I feel that when you were horrible at your job for over five years, a change is long overdue.  To give you an idea of how bad Littlefield was, and using the recent Morris release as a reason to post thislist, I will give to you the very best worst of Dave Littlefield.

The Draft

In 2002 the Pirates had the first overall pick, with BJ Upton being the consensus best player in the draft.  Littlefield selected Bryan Bullington with the first pick, then followed that up by announcing that Bullington could eventually be a #3 pitcher in the majors.  Players taken after Bullington:  BJ Upton, Zack Grienke, Prince Fielder, Jeff Francis, Jeremy Hermida, Joe Saunders, Khalil Greene, Scott Kazmir, Nick Swisher, Cole Hamels, James Loney, Jeff Francoeur, Joe Blaton, and Matt Cain.

In 2006 the Pirates had the fourth pick, and selected Brad Lincoln.  Pitchers who went off the board after Lincoln:  Brandon Morrow, Andrew Miller, Clayton Kershaw, Tim Lincecum, Max Scherzer, Ian Kennedy, and Joba Chamberlain.

In the 2007 draft the Pirates had the fourth pick, with a big need for offense in their minor league system.  Catcher Matt Wieters was widely considered the best offensive pick available for the Pirates, but was a Scott Boras client, which means he would command big money.  The Pirates selected Daniel Moskos, who they projected to be a relief pitcher in the majors.  Wieters went next to the Orioles and signed for a $6 million bonus.

The Trades 

Littlefield also had a horrible history with trading players.  His first trade sent rising star pitcher Jason Schmidt to the Giants for Ryan Vogelsong and Armando Rios.  John Vander Wal was also sent to the Giants in a part of the deal.  Vogelsong eventually became a mop up pitcher out of the bullpen, while Rios failed in center field.

In 2003 Littlefield traded rising star Aramis Ramirez and Kenny Lofton to the Cubs.  In return he received Jose Hernandez (yes, the strikeout king), minor league pitcher Matt Bruback, and a player to be named later, which Littlefield claimed the fans would love.  That player ended up being Bobby Hill, who eventually became a bench player and is probably out of the majors at this point.

Before the 2003 season Littlefield traded two pitching prospects to acquire reliever Matt Herges.   One of those prospects is current Padres ace Chris Young.  As for Herges, he was released from the team during spring training.

At the 2004 trade deadline the Pirates traded Kris Benson to the Mets (back when Benson was decent), and in return received Ty Wigginton (to be their long term answer at third base) and pitching prospect Matt Peterson.  The Pirates also sent Jeff Keppinger in the deal to re-acquire Jose Bautista (more on Bautista later.)  The worst part of this deal was that the Devil Rays traded Victor Zambrano for Scott Kazmir on the same day.  Littlefield could have taken Kazmir, since Benson was the better pitcher, but wanted to get Bautista back (again, more later.)

Before the 2004 season the Pirates traded pitching prospect Leo Nunez to the Royals for aging catcher Benito Santiago.  Santiago was horrible for the Pirates and was released after only a month.  Nunez is now a solid reliever for the Royals.

In the 2007 season the Pirates, after passing on Matt Wieters, presumably because of the high cost to sign him (signed with the O's for $6 M) traded Rajai Davis to the Giants for Matt Morris, taking on the entire $14 M due to Morris at the time.  Also at the time Morris was sporting a 7+ ERA, and would serve no help to the Pirates, who weren't expected to contend in the 2008 season.

Trades that worked despite Littlefield

Littlefield managed to pull off two deals that worked.  In the first deal he sent star outfielder Brian Giles to the Padres in exchange for Jason Bay and Oliver Perez.  Bay became a star for the Pirates, while Perez had a breakout year in his first season with Pittsburgh.  The problem is that Littlefield wanted Xavier Nady, and settled for Bay.  At the 2006 trade deadline Littlefield sent Perez, who was struggling and still under the Pirates control for a few more seasons, and solid reliever Orlando Hernandez (who would fetch a comp. pick if he was signed by another team the following season) for Nady.  Not such a bad move, but the Pirates sold low on Perez, and Perez responded by rebounding in New York.

In the 2003 season Littlefield traded solid left handed reliever Scott Sauerbeck and future closer Mike Gonzalez to the Red Sox for Brandon Lyon and Anastacio Martinez.  Lyon was the key piece in the deal, but upon reporting to the Pirates, was discovered to be damaged goods.  In a move to save face, the Red Sox agreed to another swap to right the original deal, this time accepting Martinez back, along with Pirates pitcher Jeff Suppan, who was 10-7 at the time, and Lyon.  The Red Sox returned Mike Gonzalez (who would go on to eventually fetch Adam LaRoche) and sent top prospect Freddy Sanchez.  It took the Pirates two years to realize that Sanchez was not a bench player, and was actually a prime talent, eventually going on to win the NL batting title in 2006.

Fudging up the waiver process

Littlefield was horrible at managing the roster, most importantly during the 2003 off-season.  During the Rule 5 draft, Littlefield left Chris Shelton, Jose Bautista, Jeff Bennett, Frank Brooks, and Rich Thompson unprotected, and watched them go as the top selections in the draft.  Shelton had a solid start with the Tigers before eventually fading back to a AAA player.  Bennett has been a decent reliever in the majors.  Bautista was probably the biggest loss, as the Pirates were without a third baseman, thanks to the Aramis Ramirez blunder, which forced the need to trade for Bautista at the 2004 deadline.  The Pirates protected players like Mike Lincoln, Abraham Nunez, and Joe Beimel, and also had three roster spots open.  They signed Randall Simon, Chris Stynes, and Raul Mondesi with those spots, with none of those players having an impact the following year.

Littlefield also lost a lot of talent on waivers.  In 2003 he waived Bronson Arroyo, who went on to have success with the Red Sox.  In the 2003 off-season he waived Duaner Sanchez and Matt Guerrier, who are both solid relievers in the majors to this day.

The major issue with Littlefield was his need for a quick fix.  He didn't know how to be a General Manager for a small market team.  He was constantly looking for average major league ready talent, rather than going for the high risk, high reward prospects.  This explains spending $14 M on Matt Morris, but passing on signing Matt Wieters for $6 M.  This also explains trading for Ty Wigginton rather than Scott Kazmir.  To recap, the Pirates lost the following players under Littlefield: 

-Chris Young (SD)
-Aramis Ramirez
-Bronson Arroyo
-Kris Benson
-Jason Schmidt
-Leo Nunez
-Rajai Davis
-Kenny Lofton
-Duaner Sanchez
-Matt Guerrier
-Jeff Bennett
-Chris Shelton
-Jeff Suppan
-Oliver Perez
-Orlando Hernandez
-Scott Sauerbeck

The notable Pirates players who are here now due to these deals: 

-Jason Bay
-Freddy Sanchez
-Xavier Nady

This doesn't even factor in the amount of talent the Pirates lost through the draft, going for the low risk, low reward players in the first round, rather than taking the stars that were drafted after their picks.  The Pirates are left with $11 M due to Matt Morris, and once that is paid, the Pirates can officially be finished with the Dave Littlefield era.  I am extremely happy over that.