As bleak as things have been and continue to be around the Pittsburgh Pirates sinking ship on the North Side of Pittsburgh, optimists, fans and most Pittsburgh media members continue to point to the supposed better things on the horizon. Much of that stems from General Manager David Littlefield who replaced the beleaguered Cam Bonifay. David Littlefield was viewed as a savior and a sign of things changing around this franchise which had a losing record nine consecutive years upon the hiring of Littlefield. Closing in on his fifth year anniversary as Pirates G.M., the appropriately named Littlefield is now in charge of a ball club fresh off their thirteenth consecutive losing season and well on their way to a fourteenth. With that let’s take a look back at all his transactions he was overseen and analyze them in hindsight.

            July 30, 2001

With the ink on his new contract barely dry, Littlefield unloads RHP Jason Schmidt and OF John Vander Wal to San Francisco for RHP Ryan Vogelsong and OF Armando Rios.

Schmidt closed off his 2001 campaign in San Francisco by going 7-1 and then put up win totals of 13, 17, 18 and 12 in his next four seasons. He started in the 2003 all-star game (opposite of another ex-Pirate Esteban Loaiza) and was the ace of his team that advanced to the World Series. Rios came to Pittsburgh on two bad legs that plagued his short lived stint of 78 games in one and a half seasons. Vogelsong never lived up to his promise and posted ERAs of 12.00, 6.55, 6.50, 4.43 and currently 5.14 on this year’s squad. His role is that of a mop up relief to come in after the Pirates games are already out of reach.

Analysis/Grade: It did not take long for Littlefield to pick up right where Bonifay left off with terribly uneven trades. The terrible careers of Vogelsong and Rios only further enhanced the criticism over this trade. F

            July 31, 2001

Not fully content with acquiring Rios and Vogelsong, one day later Littlefield went out for more. Dealing closer Mike Williams to Houston, the Pirates landed another troubled arm. Tony McKnight lasted all of 12 games with the Pirates where he went 2-6 with a 5.19 ERA.

Analysis/Grade: Luckily for Littlefield Williams came back to Pittsburgh a year later. D

            December 13 2001

After the transaction log of the Pittsburgh Pirates consisting mostly of Armando Rios being sent to the Disable List for 15 and 60 day stints, Littlefield finally struck again. He cranked up the hot stove in Pittsburgh by acquiring Kip Wells, Sean Lowe and Josh Fogg for Todd Ritchie and Lee Evans in a deal with the White Sox. Wells compiled a record of 35-48 while with the Pirates. Josh Fogg was 39-42 but his ERAs ranged from 4.30 to 5.26 in his four seasons in Pittsburgh before being released. Ritchie’s career went into melt down mode after leaving Pittsburgh going 6-19 before retiring.

Analysis/Grade: Fogg and Wells provided the bulk of the innings for the Pirates over the next three years; however their consistently pedestrian numbers kept the Pirates mired in their cycle of 90-100 losses. Still was a great return for unloading Ritchie before his career began to wind down. B+

            January 2002

During that same off-season, Littlefield managed to lure back Mike Williams who would go on to set the franchise record for saves in a season and make an All-Star game. However he would also agree to contracts with Adrian Brown, Abraham Nunez, oft-injured Armando Rios (not giving up on his first trade of his Pirates tenure quite yet) and Sean Lowe. He also set to change the perception of free agents not wanting to come to Pittsburgh by signing Pokey Reese. In less than two seasons in Pittsburgh Pokey batted .253.

Analysis/Grade: The off-season made baby steps in attempting to change the conception of the Pirates off-season free-agent handlings. However none of them would pan out besides Williams to a certain extent. C

            February 28, 2002

Showing that the Pirates are serious about keeping around young home grown talent, the Pirates secure the cornerstone of their franchise, 3B Aramis Ramirez to a three-year contract. In hindsight however, the contract proved too much for the organization to handle which would lead to a debacle that deprived nearly any Pirate fan of ever having hope in the organization again.

Analysis/Grade: The effort and goal was there, and a statement at the time was made about the Pirates being serious when it came to keeping their own young talent around for the long term. We will get to the financial implications of the deal later bat at the time… A+

            July 31, 2002

To celebrate the one-year anniversary of giving away Jason Schmidt to San Francisco, David Littlefield made a relatively meaningless trade by sending OF Chad Hermansen to the Cubs for OF Darren Lewis. This discussion would not be complete without saying that Lewis announced his retirement from baseball two days later.

Analysis/Grade: Dumping Hermansen was about two years too late, they gave this career minor leaguer way too many opportunities to prove himself and he never quite did. The Lewis situation only highlighted the bleak picture of baseball in Pittsburgh. C-

            November 2002

Littlefield finally cut his losses with Rios by releasing him. But a locker room dividing situation over injured Pat Meares continued as Littlefield reinstated him from the 60-day disabled list.  Later that month 1B Randall Simon was acquired from Detroit in exchange for a group of minor leaguers. The free-swinging overweight first basemen most known for hitting a girl dressed up as a sausage in Miller Park batted .244 with the Pirates.

Analysis/Grade: Getting rid of Rios was a good move, but not settling the Meares situation divided the clubhouse even more. Simon added some pop to that lineup and the Pirates did not give up much in return. B

            December 2002

In a colossal waste of money, Littlefield overpaid RHP Brian Boehringer on a two-year deal. 2003 would see him post a 5.49 ERA and then collect his paycheck during 2004 while he was injured for nearly the entire season. In what would become an off-season tradition, Littlefield added another journeyman with a weak bat in OF Matt Stairs. Two days later Littlefield acquired Matt Herges from Montreal for two minor league pitchers. One of those was Chris Young.  Young would go on to post a record of 18-11 in over two seasons with Texas and San Diego. At only 27 years old and 6 foot 10 he has one of the most promising careers of any American League pitcher and is currently being paid only $500,000 a year. Matt Herges never made it past spring training.

Analysis/Grade: This is one of many examples of Littlefield and the Pirates inability to evaluate talent properly. This was not a salary dump, this was just poor evaluation of what they had. Young is one of those examples out there that shows it does not take a huge payroll to compete, just a little competence. F

            January- March 2003

The hot stove of 2003 was cranked up once again in Pittsburgh, maybe a little behind the other markets but nonetheless Littlefield was determined to spend. He brought in inning-eater Jeff Suppan as well as power hitter Reggie Sanders and Kenny Lofton.

Analysis/Grade: These veterans did greatly enhance the team and started them off with a respectable record. But in the end they were simply one year stop gaps that cost a lot of money and before you knew it gone. Lofton and Suppan played important roles in the pennant races. However Suppans was with Boston and Lofton with Chicago. A-

            May 14, 2003

The string of journeyman veterans coming aboard the Pirates roster for no apparent reason continued when Littlefield authorized the pickup and then minor league purchase of Jeff Reboulet.

Analysis/Grade: While pickups such as these do not hurt the franchise as some of the people they let go, veteran journeyman with no real contributions really dampen a clubhouse full of young promising talent. They also prevent the future of the ball club from seeing any serious playing time. D

            July 2003

Littlefield started off the July transactions by trading All-star and career save leader Mike Williams to Philadelphia for LHP Frank Brooks whose career began and ended with a 0-1 record and 4.67 ERA. The Pirates then acquired the services of Jose Hernandez whose sub .200 batting average continues to haunt them. In exchange for receiving the most prolific strikeout swinger of all-time the buccos parted ways with one of their off season stop gaps in Lofton but also with the cornerstone of their foundation and rebuilding process Aramis Ramirez for some cash and lifetime .262 hitter Bobby Hill. They also dumped Scott Sauerbeck and Mike Gonzalez for two absolute scrubs.

Analysis/Grade:  The Pirates played the most pivotal role in the 2003 pennant race by supplying the Cubs and Red Sox with most of their fire power. Mike Williams was the Pirates closer and he was gone and Gonzalez was the future closer and the Pirates tried to get rid of him. Gonzalez turned out alright but the Pirates only got him back because of a damaged goods technicality. It was by complete accident they still had Gonzalez in the fold, furthering the notion that the Pirates are incompetent when it comes to evaluating talent, especially their own. The dumping of Ramirez proved to be the darkest day of this century’s Pirates. Not only could the Pirates not afford to compete with higher market teams but they could not even maintain the contracts THEY signed for THEIR own talent. Receiving almost nothing in return showed that the ownership group had serious cash flow problems and was nearly unable to make payroll. McClatchy deserves some blame but Littlefield nor anyone else in the organization gets off the hook for this one. F

            August 26, 2003

Littlefield finally ended the speculation and dumped their highest profile bat 26 days after the non-waiver trading deadline but just before the trading deadline ended. In exchange for the best hitter on the team the past three seasons, Littlefield gained future National League Rookie of the Year Jason Bay as well as future ace of staff Oliver Perez. This deal looked solid at the time but Littlefield looked more and more like a genius as Perez turned out to be the ace of the staff with his high strikeout numbers and ability to draw a walkup crowd to a game. Jason Bay’s slugging numbers were unheard of for a rookie and he easily won Rookie of the Year. Giles was hitting above .300 while being as consistent as possible for a homerun hitter clubbing 39, 35, 37 and 38 homeruns with the Pirates. He went on to post similar slugging numbers with San Diego after the trade. Bay still hit solid but his numbers drastically declined from his rookie campaign and Perez would flame out over 2005 and 2006 posting ERAs of 5.85 and 6.98 while teetering on the brink of being sent down to the minor leagues.