The Pittsburgh Pirates, on paper at least, got extremely lucky when they hired Ben Cherington. Without a doubt, Cherington is the most decorated GM to be hired in Pirate history. The Pirates hired their first General Manager in 1946 – his name was Ray Kennedy. Between Kennedy and Cherington, the Pirates have hired ten GMs, not a single one had a World Series ring before coming to the Pirates. In fact, the majority of those GMs had not even held a GM position previous to being hired by the Pirates.
Cherington has high-level experience in two different organizations and saw success in both of those positions.