The Pittsburgh Pirates traditionally do not spend a whole lot of money in Free Agency. This also suggests that the team traditionally does not sign many players of prominence.
Unfortunately for the Pittsburgh Pirates and their fans, many of the free agents that the Organization has brought in have not really worked out. That tends to happen when you play pretend and do not actually invest in the team but rather just trying to fill holes with aging veterans or busted prospects. Obviously though, through the years the team has made some deals bad or good.
However, that has been the curse that has hung over the Pittsburgh Pirates for the better part of the last 30 years. The reality is these moves have traditionally not worked out for the Pittsburgh Pirates. Even during their few competitive years, from 2012-2016, the team struggled to bring in outside talent.
The Pittsburgh Pirates deserved to be criticized for the way their team operates especially in free agency. Up until this year, the Bucs were hardly even handing out Major League contracts let alone aggressively pursuing upgrades. Maybe it is because they have been burned in the past, spending resources and not getting any positive results from the deal. Why spend now if you are not going to win? Still, every team in Baseball needs to be successful in some capacity in Free Agency. The Pittsburgh Pirates have not had this success, let's take a look at their 15 signings that wound up being failures.