Pittsburgh Pirates: Assessing the Best Free Agent Signings of the Past 25 Years

Which GM has the best track record of attracting talent to Pittsburgh?
Milwaukee Brewers v Pittsburgh Pirates
Milwaukee Brewers v Pittsburgh Pirates / Joe Sargent/GettyImages
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In this, the 25th offseason of the 21st century, Pirates general manager Ben Cherington has been the subject of criticism (or at least questioning) as fans clamor for a big free-agent signing, but how does Cherington’s time at the helm compare to his predecessors?

As a small market, Pittsburgh often does not figure as a major mover or shaker during the offseason, but like every MLB franchise, the Pirates have enjoyed a few surprising pickups and lamented their fair share of busts. Starting with the 1999-2000 offseason, I attempted to assess the value of each free-agent signing with a particular emphasis on on-field performance and return on investment.

Relatively few impactful free-agent signings occurred in the last few years of Cam Bonifay's reign, so the focus here is on Cherington, Neal Huntington, and Dave Littlefield. To qualify for this list, the signing had to have occurred between the end of the prior season and Opening Day (approximately April 1), and if a player re-signed with the team after exploring the free-agent market, I considered all consecutive years as one signing.

This exploration resulted in a few surprises and several blasts from the past. Without any further ado, I present the Pirates’ best and worst free-agent signings of the 21st century.