There were a lot of reasons behind the Pittsburgh Pirates historic 20-year run without a winning season from 1993-2012. Some of it was due to money. Baseball’s refusal to implement a salary cap crippled small market clubs such as Pittsburgh. Poor management decisions also contributed. The Pirates were known to give out terrible contracts to players like Derek Bell and Pat Meares. That was money that could have been spent on younger, better talent. Some of the losing also came from not being able to evaluate talent like Jason Schmidt.
The Bucs also were not known for getting the most back in exchange for the talent they could not keep, which was the case with the Aramis Ramirez trade.