No matter what, Littlefield made two consecutive transactions that dumped all-star pitchers by designating Arroyo for assignment and trading Chris Young for Matt Herges. Those two moves have probably had more of a negative effect on the current franchise than any others, simply because this is an organization that claims to be built around young pitching and Littlefield dumped two young pitchers with a ton of potential for absolutely nothing.

2003 was also the year of the Aging Free Agents, as shown by Suppan. The first position player that Littlefield signed was Reggie Sanders, who ended up having one of the best seasons of his career in a Pirate uniform. Sanders’ 31 homeruns and veteran influence in the locker room were very important to the young team and Littlefield was an idiot for not resigning the outfielder after the 2003 season. Sanders is still an effective player with solid trade value now, three and a half seasons later. He’s one of those guys who is just good to have around on a young team or a winning team simply because he has a positive and calming influence on young players. The next Aging Free Agent was Kenny Lofton, who ended up having a decent half-season or so for the Pirates, but was traded later in the season. Sanders was definitely more important to the Pirates, but Lofton was a valuable stopgap for the Cubs, helping fulfill Steve Bartman’s destiny.

Littlefield released Matt Herges on March 26, effectively surrendering the Chris Young trade. This needs no more comment.

The next semi-important (but not at all) personnel moves occurred in May, as Jeff Reboulet and Pat Mahomes made their Pirate debuts. Both men were awful major league players (think Matt Kata and Josh Sharpless, but somehow worse) who never should have set foot on the dirt at PNC Park. They were, however, apparently the best options at the time. Oh well. They can’t have done too much damage simply because I don’t remember anything egregious involving either one of them. And calling up Mahomes got rid of Denys Reyes, who was the Blimp before the Blimp came to Pittsburgh.

Littlefield’s draft in 2003 was headlined by Paul Maholm in the first round and Tom Gorzelanny in the second round, two pitchers who are seemingly on their way to becoming mainstays in the Pirates’ rotation. The rest of the draft, however, featured a whole lot of nothing. Other notables included:

• Pedro Powell, who has 44 stolen bases but a .240 average at Lynchburg
• Steve Lerud, who was supposed to be one of the next catching prospects but has a .216 average and one home run at Lynchburg
• Craig Stansberry, who was born in Saudi Arabia and had some success with the bat and glove in the Pirate organization only to be released before this season. Stanberry has had significant success this year, as he has a .289 average with nine home runs, 54 RBIs and nine stolen bases at San Diego’s AAA team.
• Adam Boeve, the hitter who seems to be a somewhat interesting prospect (but not really), who was turned into another product of the Pirates’ hype machine due to his 56 homeruns in 2004-05 only to disappoint in 2006. He’s actually having a decent year this season and will probably pop up in Pittsburgh as a bench player for a short stint eventually.
• And Josh Sharpless, the local product who looks like a potential prospect if you look at his stats, but is legitimately awful if you see him in person. He is a AAAA pitcher.

The See If You Can Eat a Pizza Before Mike Williams Ends This Inning Game came to an official end on July 20. For the record, I only saw the feat accomplished once, but it occurred with a technicality because Williams didn’t get out of the inning. The pizza was still gone before the inning ended, though . . . As for important matters, the Pirates received Frank Brooks in the trade. Brooks was a AAAA reliever, essentially unimportant, but it always seemed like he could have been decent. The important part was just that the Pirates were no longer paying Mike Williams, who should have had a contract with UPMC concerning the baserunners he let on because I’m certain that he gave a significant number of people blood pressure problems.

The fun really began in earnest, however, on July 22. That was the day that Aramis Ramirez and Kenny Lofton were shipped out to Chicago, a place where Ramirez still terrorizes the Pirates, for Jose Hernandez, Bobby Hill, and a bag of balls better known as Matt Brubeck. The Pirates made the trade because they needed to save $6 million somewhere for the next season, and Ramirez and Kris Benson were the two players with the six million dollar contracts. The issue, though, is that Littlefield was somehow only able to receive three scrubs for one of the premier young third basemen in baseball. Honestly, that’s the type of trade that a small market team simply can not afford to make. If they were going to dump one of the players, it would have been much more beneficial to the team to dump Kris Benson, his faux-injury troubles, and his wife instead of Aramis Ramirez and his ideal #5 in the order bat. Think about Jason Bay’s stats the last two and a half seasons if he has Ramirez protecting him. They would be that much more impressive. This was simply an idiotic trade forced by cheap management where damage was increased because Littlefield picked the wrong player to trade away for nothing.

Littlefield proceeded to outsmart himself in his dealings with the Boston Red Sox. The first trade he made with the Ole Towne Team occurred on July 22, with Scott Sauerbeck and Mike Gonzalez (yes, that Mike Gonzalez) heading to Boston in exchange for relievers Brandon Lyon and Anastacio Martinez. It turned out that Lyon’s arm was ready for massive surgery, something that Littlefield apparently didn’t know about until the pitcher was already in Pittsburgh. This resulted in a grievance being filed by the Pirates against the Red Sox and what amounted to a trade-back occurring. In this trade, the Pirates threw Jeff Suppan (meaning they didn’t get the pitcher in 2004) in, along with the two pitchers that they received from the Red Sox in the first trade (Lyon and Martinez) and received Gonzalez and Freddy Sanchez, along with cash, from the Red Sox. If Brandon Lyon’s arm had been fully healthy, therefore, the Pirates would not have had Freddy Sanchez or Mike Gonzalez last season and the year would have been that much more miserable. Dave Littlefield received a huge break with that series of dealings, but the fact that he messed them up in the first place can not be underestimated simply because it was such an awful deal before Lyon’s injury.

The Brian Giles trade went down on August 31, the last possible day. The trade of the franchise’s cornerstone netted future All-Star Jason Bay and enigmatic pitcher Oliver Perez, along with Cory Stewart. Considering that Littlefield went into the negotiations trying to get Jake Peavy and Xavier Nady, the trade can be considered something (but only something) of a disappointment. It is unfair to call this trade one of Littlefield’s better ones, however, as any time a perennial all-star is traded, two very good prospects should be the minimum that is received in return. I give Littlefield a B on the trade and I have the right to change that grade at any point, depending on how Jason Bay is hitting, especially considering that the trade ended up being Brian Giles and Roberto Hernandez for Xavier Nady and Jason Bay due to the deals at last year’s trade deadline. Essentially, Giles netted the Pirates 2/3 of their starting outfield, and that is a successful (but not great, considering the potential he could have received) trade.

On October 1, the Pirates claimed Jason Boyd off of waivers. Wow. Yup, that’s a typical Pirate move. Pick up a reliever off of the waivers, stick him out there, realize after we have him that he is a terrible player, keep him around for a while because we’re paying him, disappoint the fans, release him at last and claim that the next option is better. Wash. Rinse. Repeat.

Another ugly day occurred on November 20, as three Pirates were claimed off of waivers: Walter Young (essentially a Ryan Howard who completely failed to develop), Duaner Sanchez (the reliever who never really got a chance here, but was somehow good enough for this season’s and last season’s version of the New York Mets), and Matt Guerrier (the stats say it all).

The next genius move was not offering arbitration to about five players (including Tavarez, Sanders, Stairs, and Pokey Reese). These guys could have at least gotten some supplemental draft picks and to not give any one of them arbitration is just lazy management and how to avoid making a small market winner in order to save money. It was just ridiculous.

The year ended on a fantastic note, as the Pirates signed Chris Stynes to be their everyday third baseman the next year. We all know how that turned out. If fans want to look at one year as being the downfall of this franchise, it has to be 2003. From letting potential draft picks walk away to dumping off budding superstars in order to save money, this season is the defining one of the Littlefield/Nutting/McClatchy regime.

And there are at least four more to go in the series.

His next move was to extend spring training invitations to about ten players, including Salomon Torres. That moves deserves an A, simply because Torres proved to be ready to return to be a successful pitcher in the major leagues. Brian O’Connor, Kevin Tolar, Jason Rakers, etc? Not so much.

On January 22, Littlefield named two “Special Assistant[s] to the General Manager.” What does that job entail? Does anybody really know?

Littlefield’s next move was to invite another slew of relief pitchers to spring training, including Brian Boehringer, Al Reyes, and Chris Spurling. Adam Hyzdu and Louis Polonia were also included in this batch, as Littlefield seemed to be good at finding potential and then not letting it develop at this point in time, whereas he just doesn’t even bother finding the potential now.

On January 30 he made one of the largest free agent signings in Pirate history (doesn’t that say something about the franchise), as Pokey Reese inked a two-year deal. Pundits at the time saw this as a turning point for the fortunes of the franchise, thinking that by signing a decent second-baseman the Pirates were about to become a player on the yearly meat market that is free agency. This conception is obviously wrong, as Reese is still Littlefield’s biggest free-agent signing (not counting Raul Mondesi) during his tenure as Pirate GM. The signing was just another aberration from Littlefield in his first half-year as general manager.

Next came the annual act of signing over the hill pitchers to contracts and inviting them to spring training, including Pat Rapp, Ron Villone, and Josias Manzanillo. Manzanillo and Villone both made minimal contributions, unless you count Manzanillo’s ability to jump ridiculously high off of the mound after he struck opposing batters out. But, then again, they could have made a jumping bobblehead or had a Jump like Josias night . . . oh the missed promotional opportunities with that.

Littlefield’s next move was actually an intelligent one, but it came around to bite him in the butt as he signed Aramis Ramirez to a contract extension through 2004, buying out his arbitration years. The contract included, however, a $6 million salary in 2004, leading directly to the franchise’s cornerstone being dumped at the 2003 trade deadline.

On March 13, the Warren Morris experience came to an end as the former Rookie of the Year candidate was finally released from the pain and misery of being a Pirate farmhand and Pirate fans were released from having to hear the name Warren Morris over and over again.

Littlefield’s first trade of the new year occurred on March 27, as he sent Damaso Marte and a minor-league catcher to the White Sox for farmhand Matt Guerrier, a solid relief pitching prospect. This was the first sign of a Littlefield-type move, giving up a strength for more relief pitching. The Marte trade was the first sign that this man may not quite know what he’s doing, after all. Granted, Guerrier turned out to be a pretty decent pitcher (that will be detailed later in this series), but Marte was obviously somewhat valuable and showed the signs of at least becoming a solid relief pitcher.

March 30 signified the end of the Derek Bell Era, as Operation Shutdown was put out of business. One of my life goals is still to get Derek Bell as a boat guide some day and just heckle him about his Pirate career.

Not much happened until July in terms of personnel moves, outside of the usual disabled list shenanigans that occur on any given team over the course of the year. The only interesting development was Littlefield’s calling up and sending down Bronson Arroyo, who has stated publicly (SI magazine) that the Pirates’ minor league coaches tried to convince him to change his pitching motion, leading to much worse performance from the now All-Star pitcher. More great instruction by the Pirates’ staff.

July of 2002 was relatively uninteresting in terms of trades, especially by the Pirates’ standards. Only two established players were traded, with Mike Fetters going to Arizona for prospect Duaner Sanchez (a very good trade by Littlefield, who seems to have a knack for picking relief pitchers) and the Chad Hermanson Experience finally came to an end.

The Hermanson trade was particularly interesting, as the Pirates traded the player who had once been the future of the franchise for Darren Lewis. This trade is only noteworthy because it occurred on July 31, 2002. Darren Lewis retired on August 2, 2002.

Now, the trade was probably made so that Littlefield could have a roster spot for Armando Rios and so that Littlefield could be done with Chad Hermanson, but still. When a player is retiring two days after you trade for him, that is not a good sign.

The only other noteworthy move in August was the release of the Flying Pitcher, Josias Manzanillo, on August 14 after struggling for most of the season (7.62 ERA).

One of the more humorous/eye-catching events of Littlefield’s tenure occurred on September 8th, as Sean Lowe game up one run in one-third of an inning during a 11-1 loss to the Florida Marlins and was then promptly granted his release after the game. This is the type of accountability that the franchise needs today.

November was a very fun month for the franchise, as the Pirates named Gerald Perry hitting coach and Alvaro Espinoza minor league fielding coach. Espinoza is still around somewhere, but Perry left with Lloyd McClendon and is now the hitting coach for the Chicago Cubs. Good enough for Lou Piniella, but not good enough for Jim Tracy, eh?

On November 20, Littlefield purchased the contracts of several minor-leaguers, who have all become contributors to the team, but that group included Walter Young. In order to do so, he released Armando Rios, therefore surrendering half of the Jason Schmidt trade, and designated John Grabow for assignment. Littlefield did not view a pitcher who is now a staple of the bullpen as being good enough for the team back in 2002, but viewed Walter Young as being important to the team.

Littlefield made another one of his trades on November 25, sending minor league reliever Adrian Burnside and two players to be named later to the Tigers for Randall Simon, who will be forever remembered for hitting the sausage (view the Top Baseball Fights post), not for hitting a top of the ninth inning homerun in Cincinnati to win a 1-0 game in his final season as a Pirate.

The fun really got started on December 16, however, as Littlefield removed the ever-present specter of the blimp formerly known as Jimmy Anderson from the friendly confines of PNC Park. Even more interesting about that day, however, was the fact that the Pirates had two players (D.J. Carrasco and Chris Spurling) picked in the Rule 5 draft, a prelude to the 2003 debacle. Even more ironic is the fact that both pitchers were relievers, exactly the type of guy that Littlefield has kept around through thick and thin over most of his time in Pittsburgh. Even more interestingly, however, is the fact that Ronny Paulino was picked in the second round by the Kansas City Royals. Yes, Littlefield almost let the player who would become his starting catcher leave for nothing except for $50,000. Wow.

Two days later, Matt Stairs signed a one-year contract, which actually turned out to be a decent deal for the Pirates. Any potential good will incurred by that signing, however, was promptly lost two days later with the Matt Herges trade.

Or maybe it should be called the Chris Young trade, as the Pirates traded the 6-10 pitcher, the one with the 1.97 ERA, to the Expos for Matt Herges, a relief pitcher who was released shortly thereafter. The idea of trading a pitching prospect, particularly one who has shown the potential to become a very good starter, for a mediocre at best relief pitcher is simply a terrible idea and goes against all of the most basics tenets of how to run a small market team.

Littlefield began to show that he just doesn’t get it with that trade.

The fun started immediately, as 2001 was the year when the Pirates held the Jason Schmidt Sweepstakes, Littlefield’s first big project. He ended up getting an outfielder with scary comparisons (Gerut and Nady) and a rag-armed pitcher for the future ace. Schmidt, therefore, was the first Pirate who Littlefield gave up for nothing and went on to succeed somewhere else. Littlefield’s other notable moves that trade deadline were trading for Tony McKnight, who could seemingly only pitch against the Pirates and was out of baseball half a season later, and getting Adrian Burnside and Mike Fetters from the Dodgers for Terry Mulholland. This was actually a pretty solid trade for Team Littlefield and is, therefore, unworthy of mention in this article.

Littlefield’s next major personnel moves came on November 28, 2001 as he hired Ed Creech as his scouting director (oh GOD!) and purchased the contract of J.R. House, therefore adding the potential quarterback who was not afraid of a linebacker but was afraid of a baseball, to the 40-man roster.

December 2001 was a particularly fun month for Littlefield, as he named Brian Graham Director of Player Development on the third, therefore messing up the next generation of Pirate prospects for years to come. This move, however, was not anywhere near the most important or the worst one that month. And, for once, these are two separate moves instead of the same move.

The most important move was shipping Todd Ritchie and his fluke good decent years to the White Sox, who had become sick of the Kip Wells experience, for Wells, Josh Fogg, and Sean Lowe. The move showed insight on Littlefield’s part as he managed to dump one or two good seasons for about ten years of Pirate starters, which is always a good trade. Kip Wells, though, is like Kris Benson except the team was willing to trade him before he could get pitching coaches fired. Fogg, meanwhile, is a typical back of the rotation innings eater who simply goes out and throws the ball over the plate, getting hammered occasionally and having a good start about once a month. This was a very good trade for Littlefield and the Pirates.

Littlefield, however, could not keep up his successful run as he traded Gary Matthews Jr. to the New York Mets later that month for future considerations, presumably to make way for the one and only Chad Hermanson. Yes, that Gary Matthews Jr. and that Chad Hermanson. Littlefield, therefore, guessed wrong and kept the wrong young centerfielder, choosing the homegrown kid over the one already in the majors.

2001 was actually a decent year for Littlefield, thanks to the Mulholland and Wells deals. He ruined the team’s future, however, by naming Brian Graham director of player development (HA!) and Ed Creech Director of Scouting (Yup, that’s worked out.).

There is plenty to knock here, but Littlefield certainly showed potential and seemed worthy of another year at the end of 2001.

With that said, we are going to start a new series counting down to the trade deadline called Littlefield’s Looneys, a play on the Leftfield Looneys. A new year will be posted every three days from here on out, detailing the trades and personell moves that Littlefield made that calendar year, from the Todd Ritchie trade to the Chris Stynes signing to his obsession with Randall Simon. The series will end up on July 31 and, surprise, surprise, a new year of trade deadline moves will have been consumated.A quick note on the date and calendar day. It is probably never a good idea to hire someone on a Friday the 13th, as Littlefield was. That’s simply not the way to start a new time in franchise history, even if you are the Pirates and anything seems like it could be a positive change. The schedule, therefore, will be:

July 16 – 2001

July 19 – 2002

July 22 – 2003

July 25 – 2004

July 28 – 2005

July 31 – 2006

Certainly to be followed shortly by a strong lashing of whatever moves Littlebrain makes at this trade deadline. Don’t forget to check back regularly for new stuff.