December 2003

     The Pirates became the laughingstock of the league during the Rule 5 draft when other major league clubs raided the Pirates unprotected list for prospects. The ball club in Pittsburgh made sure to protect the likes of Tony Alvarez, Carlos Rivera, J.J. Davis, Jason Boyd, Mark Corey and Corey Stewart who they refused to give up on, but none of which reside on their roster right now. However they deemed Chris Shelton expendable and did not protect him leaving him for the Detroit Tigers to steal in the Rule 5 draft. Somehow despite hitting .340 with 17 homeruns in less than 100 games in single A ball and then .359 with 21 home runs in 95 games in AA ball and clearly being the best hitting prospect in the organization, the Pirates deemed five other plays that had less than a percentage point chance of reaching the majors to be more valuable.

Analysis/Grade: The Rule 5 draft proved to be pure simple incompetence. The Pirates even traded back for a prospect they lost in that draft. The inability for anybody in the organization to properly evaluate what the Pirates already had on hand reached a breaking point. Shelton is the best young hitter in the American League right now and on pace for a record year in homeruns and RBIs. F

            December 23, 2003

Littlefield agreed to terms with IF Chris Stynes on a one-year deal. Stynes saw his career end as did Pirate fans as the journeyman infielder hit .216 with only one homerun in 74 games played.

Analysis/Grade: This furthered the trend of Littlefield wasting money on veterans whose careers are winding down and have no future upside residing within them. Stynes was a terrible pick up and the Pirates allowed him to forgo retirement for one more season while holding down the young Pittsburgh talent. D-

            February 23, 2004

The cold stove in Pittsburgh consisted of Randall Simon’s second stint with the Pirates (much worse than the first) and bringing aboard locker room cancer Raul Mondesi. Raul would flee the country to avoid being on the Pirates any longer (I am not making this up) and Littlefield would be forced to place him on his restricted list as of May 11. After being placed on the list Mondesi returned to the states and joined the roster of the defending world champs Anaheim Angels.

Analysis/Grade: Both free agent pickups provided close to nothing for the Pirates and the Mondesi situation painted an even bleaker picture of what the baseball hell of Pittsburgh was truly like. D-

            July 30, 2004

Dangling ace pitcher Kris Benson over all the contenders heads, the Pirates finally decided to unleash him on the Mets even though they could not get nearly what they wanted in return. In exchange for Benson the Pirates received Ty Wiggington who turned out to be the worst hitting Pirate during the rest of his stint in Pittsburgh and Jose Bautista a critical part of the Pirates future who was previously lost to the Rule 5 draft debacle.

Analysis/Grade: Wiggington was a good bat but the Pirates never utilized him correctly and bringing Bautista back was a great move but simply a cover-up of a previous blunder. There were even whispers about possibly contending right around the trade deadline in Pittsburgh but dumping Kris Benson ended all that speculation immediately. Benson would post a record of 20-15 with his next two teams. B

            November 27, 2004

Littlefield had to get rid of some of the Jason Kendall contract he was still buried under. He alleviated some of this by sending Kendall to Oakland for Mark Redman. Redman would go 5-15 with an ERA at 4.90 while in Pittsburgh.

Analysis/Grade: Kendall’s contract was something he had to get rid of and anything in return would have been a plus. However I do not know if a 5-15 record counts as something in return. B

            December 2004

The free agent market of 2004-2005 was anything but a hot stove for the Pirates. They brought on aboard the likes of Matt Lawton, Benito Santiago and Daryle Ward. The overweight un-athletic Ward would bat .249 and .260 in his two seasons in Pittsburgh while averaging less than 14 homeruns a season. They lured Santiago out of retirement for all of six games to see him bat .261 in 23 at bats and then retire. Lawton would bat a decent .273 and get on base at a .380 clip but he just took up a lot of money and was gone in a year.

Analysis/Grade: The free agent pickups continue to be laughers. These players are not even looked at by contending teams but the Pirates provide a market for aging past the prime .240 hitters who are terrible clubhouse influences. These guys more than anything show the younger Pirates how much of a business the game and how to rake as much money as possible out of the system. The Pirates would have finished last with them or without them; it just would have been a lot cheaper without. C

            May 11, 2005

Littlefield nabbed Michael Restovich who would play all of 52 games for the Pirates and bat .214. This transaction is self-explanatory and deserves no analysis or grade.

            July 31, 2005

The trading deadline and Littlefield’s anniversary came and once again the Pirates had to make some moves. They dumped Matt Lawton to the contending Cubs in exchange for Jody Gerut who shortly thereafter found himself on the restricted list.

Analysis/Grade: Another off-season pickup gone before August and Gerut proved to be a player trying to milk the beleaguered Pirate organization for all its worth while taking his time on the disabled list. C-

            November 2005

After firing Lloyd McClendon the Pirates avoided possible managers such as Art Howe, Ken Macha and Jim Leyland during the new manager search. The Pirates settled on Jim Tracy and his pitching coach Jim Colborn.

Analysis/Grade: The early word on Colborn is that he tinkered with mechanics of young Pirate pitchers that were not broken and now finds himself in a big mess. Tracy has the Pirates well on their way to a 100-loss season while of course the entire onus can not be placed on the manager. Leyland, a top candidate that was overlooked for the job currently has the Tigers as the best team in Major League Baseball. Then again with the roster in place it was tough to see what even the best manager could have pulled off. C

            December 2005

The Littlefield era became even more cluttered with overpaid veterans during this off-season. Sean Casey came aboard for over $8 million and Joe Randa for $4 million. Randa (1 HR 7 RBI) replaced recently released Ty Wigginton (10 HR 33 RBI) for a lot more money.

Analysis/Trade: Randa would also prevent young talents Freddy Sanchez and Jose Bautista from seeing considerable playing time because the Pirate motto says you can not bench a $4 million investment this early in the season. This further illustrates that baseball is not all about having a high payroll. Its just having a low payroll does not allow room for errors such as these. D

            January 2006

The tradition within the Pirates refuses to change as Jeremy Burnitz is brought aboard after his previous administration in Chicago advised him to retire. The one-year deal made him the second highest paid slugger on the team. Currently this season Burnitz is batting below the Mendoza line and has whiffed 37 times.

Analysis/Grade: The Pirates continue to allow for a market to exist for players amounting to a cancerous clubhouse presence that can not still play the game of base ball. The Pirates are either desperate to get rid of money or sincerely believe that players of Randa or Burnitz’s caliber can contribute. This shows either incompetence, inability to assess talent or just the institution that is the Pittsburgh Pirates provides an atmosphere that nourishes underperformance. D-

            Littlefield came in to a bad situation but he done nothing to make it better, he has simply added to the Pirates resume as one of the top 10 worst franchises in professional sports. The money situation is constantly tight but the looking at these past transactions it does not seem money is all that important. It comes down to the young talent in the organization and spending money to retain them (Young, Ramirez, Shelton, Benson) rather than spending money on veterans who are going to be one and done in a Pirates uniform. The minor league system is not being built up properly and most of the players down there are aging and career minor leaguers. Even if there were incredible young talents ready to emerge from AAA or AA taking a look at Littlefield’s track record would dampen any positive future outlook. Some of the veterans Littlefield does bring in have solid career numbers yet incredibly under perform while in Pittsburgh. This is a combination of older players watching their careers wind down and the institution of the Pirates makes it easy for below average performance. This is another result of bad locker room personalities constantly being brought into the mix by management.

            To compare Bonifay and Littlefield as general mangers is not easy. Bonifay excelled in the draft and is the reason any of the minor league clubs have talent on them. However his terrible judgment when it came to contract negotiations still haunt this ball club as they continued to be mired in debt from his era. Littlefield has not brought that misfortune here yet but his drafts have been very below average including passing up B.J. Upton to take Bryan Bullington who he hoped would “make a solid number there starter”. Neither would ever be able to turn this organization around but with this organization it usually takes more than a decade to realize that and for any change to come about.