I'm inspired by a similar post by Bronx Banter about the Yankees. Bronx Banter's was about the last 20 years, but there's so much more about the Pirates to hate, so I'll restrict myself to 2001-2006. With the Pirates' season getting worse by the day, it seems to be an appropriate time to wallow in their ineptitude.
With a few exceptions, I don't have any particular problem with these players as people, but rather with the thought processes that led to their acquisitions and their continued employment.
20. ABRAHAM NUNEZ: A perfectly capable glove man who Lloyd McClendon used as his top pinch-hitter because Nunez could switch-hit. This was like deciding that a jockey would be a good fighter in the WWF because of his tendency to wear colorful clothing. For his career, Nunez has a .204 OBP and a .222 SLG as a pinch hitter. In 243 at bats. In 2004 alone, he had 62 pinch hit at bats.
19. BRYAN BULLINGTON: Bullington has pitched less than two innings with the Bucs, which is kind of the point. The Pirates made him the top pick in the 2002 draft, passing on B.J. Upton. Bullington then lost velocity as a pro, stumbled through the high minors, and ended up hurt. He's currently 25, on the DL, and unlikely to ever contribute much as a Pirate. And he was supposed to be a safe pick.
18. BENITO SANTIAGO: Santiago's tenure with the Pirates was short and pointless. The Pirates took on salary and traded a real prospect in Leo Nunez to get Santiago, then 40, from the Royals before the 2005 season. Santiago got hurt, and by the time he was ready to return, David Ross and Humberto Cota had taken his job. Santiago was cut after six games with the Pirates and has never played in the majors since then. Memo to the Pirates: do not trade prospects or overpay for players who can easily be replaced by the likes of David Ross!
17. CHAD HERMANSEN: Hermansen was already a lost cause by the time the decade began, but that didn't stop the Pirates from wasting hundreds more plate appearances on him. Hermansen was a legitimately excellent prospect at one point, but he stopped hitting while he was still in the minors. The Pirates' coaching may have ruined him.
16. MIKE BENJAMIN: If Benjamin were washed up, how could you tell? His career batting line was .229/.277/.339. Despite this, he spent four terrible years with the Pirates and even received a multi-year deal from the club after the 1998 season.
15. J.J. DAVIS: A toolsy prospect who led the Pacific Coast League in slugging in 2003, Davis has probably caused me more personal grief than anyone else on this list. I thought he had a very good chance of becoming a productive, cheap regular for the Bucs. I'm still not positive I was wrong about that, because the Pirates sabotaged his career so thoroughly. Out of options in 2004, Davis made the team with a good spring training. After that, however, he was either on the bench, hurt, or "hurt" (at one point, the Pirates wouldn't activate him even though he claimed to be healthy). Davis didn't help himself by looking clueless when he did play, but with the non-opportunities the Pirates gave him, he was very unlikely to succeed. In the minors, he often took time to adjust to a new level, though he eventually hit well at the highest levels of the minors. By the time the Pirates finally got rid of him, they'd killed an entire year of his development.
14. JOSE MESA: Mesa was hard to watch even when he helped the Pirates win. Last year, he didn't do that very often. The Pirates overpaid for his services, which didn't stop them from overpaying for Salomon Torres last offseason. Handing out millions to non-elite relievers like Mesa, Torres and Brian Boehringer hasn't worked for the Pirates, and it's unlikely to unless they first build a contending team around hitters and starting pitchers.
13. JOE RANDA: Another example of Dave Littlefield's veteran fetishism. Littlefield signed Randa to a $4 million contract even though Randa was on the downslope of his career and the Pirates had a better, younger third baseman in Freddy Sanchez. Randa didn't hit, got hurt, wound up on the DL, and finally lost his starting job. Randa has been a complete waste of money so far.
12. RYAN VOGELSONG: It isn't Vogelsong's fault that he was dealt for Jason Schmidt, who eventually became one of the best pitchers in the National League. But Vogelsong's tenure with the Pirates has been horrifying, and what's even more horrifying is that it seems it will never end. Vogelsong was a disaster as a starter, and he's nearly as bad when relieving. The Pirates rarely bother to put him in games that matter, earning him the nickname "White Flag."
11. TIKE REDMAN: Despite an undistinguished minor league career - after 2002, the Pirates dropped him from the 40-man roster and no one bothered to pick him up - Redman was allowed to worsen the Pirates' offense with his slap-hitting ways for the better part of two years, often from the leadoff spot. His defense was as hard to watch as his offense - he possessed good speed in center field but took terrible routes to the ball. All this was allowed to happen because Redman was handed the center field job in 2003 after Kenny Lofton's departure, and Redman had a huge, batting-average-driven fluke of a half-season. Beware small sample sizes.
10. CHRIS STYNES: One of the worst of Dave Littlefield's bargain-bin free agents, Stynes played horribly in 2004, got dumped by the summer, and caused the Pirates to deal for Ty Wigginton. Speaking of which...
9. TY WIGGINTON: There was no reason to think that Wigginton could be any more than a stopgap at third base, but that didn't stop the Pirates from making him the centerpiece of the awful Kris Benson trade in 2004. He didn't hit at all for about a year, got into a couple of cool collisions, got sent to the minors, and actually hit decently when he came back at the end of 2005, although the Pirates didn't notice. In any case, Wigginton played hard but didn't have enough range to play third well, and he didn't hit nearly enough to compensate. Players like him are a dime a dozen, and with Rob Mackowiak already around, there was no reason for the Pirates to trade a coveted starter to get Wigginton. I'm probably ranking him a bit too high on this list, but that Benson trade really bothered me.
8. RAUL MONDESI: Mondesi was signed for no particular reason before the 2004 season, but at least he was cheap. He quit the team for reasons unknown - his official reason had to do with a bizarre series of events involving his family. The Pirates let him go and he soon signed a new contract with the Angels, suggesting that the real problem was that he didn't want to play for the Pirates. Who could blame him?
7. JOSE HERNANDEZ: Hernandez first joined the Pirates in 2003 as a player the Pirates just had to have in the Aramis Ramirez trade. He was no substitute for Ramirez, hitting .223/.282/.326 for the remainder of 2003. Jim Tracy brought him back in 2006, and he has played just as badly, occasionally while taking playing time from Craig Wilson.
6. JIMMY ANDERSON: Let's see. Anderson threw junk, had no out pitch, and never got big league batters out for any sustained period of time. In spite of all this, he made 89 starts for the Pirates. As far as I can tell, the Pirates considered Anderson a prospect in the first place because he posted low ERAs in the minors. If the Pirates had understood DIPS at the time, Anderson might never have played for them, and he certainly wouldn't have lasted in the rotation for three years.
5. JEROMY BURNITZ: The Bucs signed Burnitz for the 2006 season for a ridiculous $6.7 million. This was especially ridiculous because the signing actively made the team worse by keeping Craig Wilson out of the starting lineup. Now that it's late June, Burnitz is playing less and less. He was showing signs of decline last year with the Cubs, and those signs are getting bigger this year. Jim Tracy publicly criticizes younger players like Ryan Doumit and Jack Wilson for on-field mistakes that arguably aren't even their fault, but he defended Burnitz for not running down the line, which was obviously his fault. Figure that one out.
4. KEVIN YOUNG: Young was good in 1997 and 1998 and downright excellent in 1999, but he was awful from the minute his four-year, gazillion-dollar contract kicked in at the beginning of the 2000 season. By the 2001 season, he was blocking Craig Wilson. Here's what Baseball Prospectus had to say about the contract in 1999:
I'd say they pretty much nailed that one.
3. PAT MEARES: Another four-year contract. This one was even more inexplicable than the Young deal. Here are Meares' numbers in the three years before he signed with the Bucs:
Hand injuries aside, where is the evidence that this guy should've been a major league starter, much less the recipient of a four-year contract?
2. RANDALL SIMON The Pirates traded a semi-propsect in Kody Kirkland to get Simon before the 2003 season, even though Simon was a bad offensive player even during his 2002 semi-breakout with the Tigers. The Pirates then acquired the much better Reggie Sanders and Matt Stairs, meaning Craig Wilson had nowhere to play. Simon was, predictably, bad, but at least he was funny, gathering the Bucs a lot of attention when he used a bat to smack a teenage girl dressed as a sausage. He wasn't bad enough, though, to avoid helping the Cubs get to the playoffs after the Bucs traded him to Chicago in the middle of 2003. Then the Bucs left Chris Shelton and Jose Bautista unprotected in the 2003 Rule 5 draft so that they could re-acquire Simon along with Stynes and Mondesi. The Pirates planned to block Wilson yet again with Simon and Mondesi, although that fortunately didn't happen, because Jason Bay started the year hurt and Mondesi soon quit the team. Simon was beyond horrible in 2004, earning his release. He was awful to watch - he swung at everything (often hitting slow rollers to second), was bad on defense, and was incredibly slow.
1. DEREK BELL: In an act of desperation, Cam Bonifay signed Bell to a ridiculous two-year, $9.75 million contract. Bell spent all of 2001 either injured or playing horribly. Then in 2002 Spring Training, he declared that he'd never had to compete for a job before and that he'd go into "Operation Shutdown" if he had to compete for one. He apparently didn't notice that the Pirates possessed two substantially better options in Craig Wilson and Armando Rios. The Pirates ate Bell's contract and he disappeared - until 2006, when he was arrested for cocaine possession.
DISHONORABLE MENTIONS: Omar Olivares, Mark Redman, Jason Boyd, Daryle Ward, Carlos Rivera, Joe Beimel, John Van Benschoten, Kris Benson, Jody Gerut, Matt Herges, Armando Rios.