Five Intriguing Facts About New Pittsburgh Pirates GM Ben Cherington

The Pittsburgh Pirates recently hired their new General Manager, Ben Cherington. While we wait for Cherington to determine the direction the team will take during the off-season and into the 2020 season, let’s look at some intriguing facts about the new hire.

1. Ben Cherington is the first GM the Pirates have hired that has won a World Series

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. The World Series ring speaks for itself in Boston, and it is very difficult to find any negative remarks about Cherington’s tenure in Toronto. Hopefully, Cherington can use his experience and professionalism to turn this Pirates franchise around.

4. Cherington Preferred coming to Pittsburgh over the Giants and the Mets

Last year, the San Francisco Giants and the New York Mets were both highly considering Cherington for their open GM positions. Cherington, however, removed his name from both job searches and chose to stay with Blue Jays front office. The following year, Cherington jumped at a GM opportunity with the Pirates – to paraphrase Cherington, he said multiple times and in many ways that the Pirates were the right fit.

The Mets’ Opening Day payroll in 2019 was $149 million. The Giants’ was almost $200 million on the nose. Cherington will never have that kind of money to work with in Pittsburgh. Whether it is because Cherington wanted to try something new, try something challenging, or just likes the city of Pittsburgh, no one can deny that Cherington really wants to be in Pittsburgh.

5. Cherington is a Farm Rebuilding Wizard

Before coming to the Pirates, Cherington worked for the Red Sox and the Blue Jays. As fellow author Nicholas Caporoso wrote, Cherington drastically improved both of these farm systems during his tenure. When Cherington took over in Boston in 2012, the team had a pretty robust farm system. Most people would assume that the team’s World Series run in 2013 would have depleted that farm system, setting the team up for failure in the near future. This is quite common and is shown with teams like the White Sox in 2005, the Royals in 2015, and even the Cubs in 2016. That was not the case in Boston. In 2015, Cherington’s final year in Boston, the team had the 2nd highest ranked farm system in the MLB according to MLBPipeline – only two years removed from the World Series. The farm system was set up so well, that the Red Sox were able to ride it to another World Series in 2018.

A similar trend emerges during Cherington’s 2016-2019 stint as Vice President of Baseball Operations in Toronto. In 2016 Toronto’s farm was at the very best average. Right now, Toronto’s farm is the 5th ranked farm in MLB. Right now the Pirates have a depleted farm system, hopefully, Cherington’s magic touch can replenish the organization’s talent void sooner rather than later.