Top 5 Worst Contracts in Pittsburgh Pirates History (as selected by me):
#5: Derek Bell-2 Years, $9 Million
Reason: Hits .173 in 2001, goes into "Operation Shutdown" and quits during Spring Training 2002. Pirates pay entire $4.5 million for him not to play. Bell never plays again and is later arrested for cocaine possession.
#4: Kevin Young-4 Years, $24 million
Reason: Signs richest contract in franchise history in 1999. Has a solid year in 1999 (26 HR, 106 RBI). But production declines considerably for the remainder of the contract, before he bottoms out with a whopping .624 OPS in 2003.
#3: Matt Morris-3 Years, $27 million (Inherited contract from Giants)
Reason: In a stunning move, Dave Littlefield attempts to save his job by obtaining the services of Giants pitcher Matt Morris. San Francisco Giants general manager Brian Sabean is pleasantly surprised when the Pirates not only agree to pay all of Morris' contract, something that no other team was willing to do, but also send back OF Rajai Davis in return. Morris starts off the 2008 season 0-4 with 9.68 ERA and the Pirates release him on April 27. Morris is thrilled because he gets paid $10 million for the privilege of not having to pitch for the Pirates.
#2: Pat Meares-4 Years, $15 million
Reason: Following a good 1998 season with the Twins (9 HR, 70 RBI), the Pirates sign Pat Meares for the bargain price of $1.5 million. For reasons unbeknownst, then Pirates GM Cam Bonifay subsequently re-signs Meares to a 4 year, $15 million contract. Meares only plays 21 games for the Pirates in 1999 because of a hand injury. Meares then underwent surgery to repair the injury and returned for the 2000 season. Unfortunately, when he returned, he bore little resemblance to the mediocre player of year's past. In 2001, he played a scant 86 games and only had 4 HR, 25 RBI, and a .548 OPS. The Pirates then placed Meares on the DL for entire 2002 season. Meares filed a grievance against the Pirates, claiming that he was healthy enough to play and demanded his release. Meares dropped the grievance in October of 2002 and never played again. In the end the Pirates paid $15 million for a player who averaged 80 games per season and didn't produce even when he played.
#1: Jason Kendall-6 Years, $60 Million
Reason: $10 million for a hitter with 73 HR and a .755 career OPS.

Only the Pirates.