Pittsburgh Pirates: Expectations for Ben Cherington’s Second Offseason

(Photo by Justin K. Aller/Getty Images)
(Photo by Justin K. Aller/Getty Images) /
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The Pittsburgh Pirates are clearly in the midst of a rebuild as they finished 2020 with the worst record.  What should fans expect from the General Manager this offseason?

When Ben Cherington was hired last offseason, Pittsburgh Pirates fans were anxiously awaiting him to “blow it up”.  Fans of the Pirates wanted Cherington to announce that the team would be going through a rebuild.  Instead, Cherington said that he would aim to improve the team and continue to do so at every opportunity.

The Pittsburgh Pirates then came out and secured the first overall pick for the 2020 Draft.  It is pretty clear that the organization is in the middle of a rebuild.  Nowadays, when teams overhaul their front office and coaching staff, a rebuild is what comes next.  Even big market teams like the Chicago Cubs and Houston Astros did it toward the beginning of the team decade.  Even this year, the Boston Red Sox saw themselves finish with the fourth worst record in baseball with a new coaching staff and front office.

This is a process, Cherington has said that numerous times since taking the job last November.  There is/was a talent gap in the Pittsburgh Pirates organization.  He has worked hard to try to resupply the farm system, and did so last offseason dealing away Starling Marte.  However, that ended up being the only move, albeit a significant one at that.  Coming back in the deal were two top 10 prospects, both of whom are expected to be in top 100 prospect conversation for this upcoming year.  Many expected Cherington to settle and get the best catching prospect he could for Marte, instead he did what any successful GM does and took the best value offered.

Cherington of course also added a lot of talent through the draft and international signing period.  The Pittsburgh Pirates acquired the second best pure hitter in the 2020 Draft Class in Nick Gonzales.  They also recently added one of the top International pitchers available, 19 year old Po-Yu Chen of Taiwan.  So while Cherington has not made a ton of moves on paper, he has been able to bring back notable value.

This offseason should be a busier one fo Ben Cherington.  Cherington often commented on how he felt behind the rest of league after being hired.  It was already mid November when he was confirmed as the next General Manager, a time when a lot of organizations are putting together their offseason game plan.

Also, entering a new organization is challenging.  Cherington was coming from the American League, and likely spent little time concerning himself with the Bucs organization.  Entering a new system and the motivation to do it the right way likely led Cherington to be rather conservative.  A player like Marte, who has been a well known outfielder in this league for a while now, has an easier value to define.  On the flip side, a player like Adam Frazier who is not as well known and has less of a track record, would be harder to value.

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Cherington needed the 2020 season to really evaluate some of the other talent on the team, not only for productivity but for their value as well.  Cherington did not want to just make deals to make deals and not get the proper value before being able to evaluate the players himself.  So now that he has had that time, Cherington probably will be more aggressive.  He should have a better understanding on who is part of the future, who is not, who is worth what, and a better grasp on the Pittsburgh Pirates farm system.