It would be hard to craft a definitive list of the biggest mistakes the Pirates made over the past 16 losing seasons. But if you were going to compile a roster of the players who most contributed to the team's pitiful record, here are some contenders.
1B: Kevin Young -- Young served two tours with the Buccos from 1992 to 2003, with a one-year break in Kansas City. His second Pittsburgh stint started well, with a full-season career-high .300 batting average in 1997. But after the Pirates pitched him a four-year, $24 million deal, Young's numbers went south. By the time he was cut in '03, he was batting a measly .202.
2B: Bobby Hill -- In 2003, the Pirates picked up Hill and two other players by trading Kenny Lofton and Aramis Ramirez to the Cubs. "When we made the deal, I told everyone it wasn't as one-sided a deal as people thought," Cubs general manager Jim Hendry told MLB.com at the time. Two years later, the Pirates knocked Hill down to the minor leagues. Ramirez, on the other hand, has been an All-Star twice.
SS: Pat Meares -- The Pirates pumped more than $16 million into Meares' pockets, and got little in return. In 2002, after two-and-a-half seasons of mediocre production, management put Meares on the disabled list for the season because of a hand injury. Meares fought with the team to get back onto the field, but dropped his grievance in October, agreeing to finish his contract on the disabled list in '03.
3B: Joe Randa -- Pittsburgh sometimes serves as the Vegas of baseball, a place where fading stars are given a final turn in the limelight. Take past-his-prime Joe Randa: The Pirates gave him $4 million to trot it out one more time in 2006. Randa, who was 36 at the time, played in 89 games that season, recorded 55 hits, and retired in November.
OF: Raúl Mondesi -- Mondesi signed with the Pirates before the 2004 season, but played only 26 games before leaving to settle a legal dispute. In an interview from the Dominican Republic, Mondesi told the Pittsburgh Post-Gazette that former major-leaguer Mario Guerrero was threatening to seize his property, and scaring his family in the process. The Pirates released Mondesi on May 19 -- though he later protested that although he left the country, that didn't mean he was unwilling to play in Pittsburgh.
OF: Derek Bell -- After the Mets let Bell slip away at the end of the 2000 season, the Pirates signed him to a two-year deal. In his first season he hit .173 and, as the Post-Gazette's Robert Dvorchak put it, "became the personification of everything that went wrong under [general manager Cam] Bonifay's five-year plan." Bell managed to top that in 2002 by collecting a check while refusing to compete for his position in what he called "Operation Shutdown."
OF: Jeromy Burnitz -- The Pirates offered the former All-Star a fat $6.7 million to end his career at PNC Park. In 2006, Burnitz hit .230 with just 49 RBIs. Give the guy credit for having a sense of humor, though: In a May 2006 Post-Gazette interview, Burnitz admitted, "This is the first team I've been on in a couple years where I'm Joe High-Paid Free Agent. That, in and of itself, should tell you the big picture that the team's in."
C: Benito Santiago -- Santiago was an NL Rookie of the Year, three-time Gold Glove winner and five-time All-Star. Problem is, that was all well before he came to Pittsburgh. By the time the Pirates acquired him in 2004, Santiago had been in the league nearly 20 years. He'd also been in a car crash and had his hand broken by a wild pitch. Santiago played in just six games before leaving the major leagues for good.
P: Take your pick. -- Matt Morris, Ryan Vogelsong, Bryan Bullington, Jimmy Anderson ... the list goes on.