Is GM Ben Cherington Planning to Stay the Course?

11-9-24 – By Josh Booth – @bridge2buctober on X

This offseason, Pittsburgh Pirates’ General Manager Ben Cherington finds himself at a pivotal crossroads. Having dedicated the past five years to meticulously rebuilding the team, Cherington now faces a “prove-it” year. That comes with a decision: stick to the plan or take a 90-degree turn?

Will Cherington be willing to top Francisco Liriano’s top free agent contract (3y $39M in 2014) to sign a high-impact free agent? Or will the GM orchestrate a marquee trade to improve the offense? Cherington’s tenure with the Pirates has been marked by patience and a commitment to building from within. The farm system now includes a wealth of promising pitching prospects. Pitchers like Paul Skenes and Jared Jones have led the headlines at the major league level. However, the offensive side of the picture is in stark contrast, testing the patience of a fan base hungry for success.

Be that as it may, it appears the pressure is mounting for Cherington and company to show tangible results. Who ever you would like to blame for this is up to you. Unlike blame, our opinions don’t carry much weight when it comes to deciding what they decide to do.

Our conversations and observations have led most of us to believe that this GM has one more shot to prove he’s done enough to remain in this position. While we are so adamant that changing the plan right now is the only way to go, it is entirely plausible that GMBC plans to stay on course with what he’s done.

“Year six,” right? Everyone involved knows that it’s time. Whether you’ve been saying that for a couple years or you are on the same page as this front office. Pirates’ fans have their minds made up what a successful offseason looks like, and it has nothing to do with the number of wins this club has in September 2025. For this front office, it is ONLY based on the number of wins in October 2025.

It took five years to build whatever you call the state of this organization. If GM Ben Cherington believes in the development of this system, his strategy could look a lot different than mine and yours. What does he prove if he makes a 90 degree turn and does something entirely different from the strategy? He proves he was wrong and wasted years in the position. But if he stays the course and in September 2025, this team reaches 85 wins and is in a playoff race, he proved himself right.

A long time to find real answers, I know. Don’t worry, we’ll all still share our opinions. That’s what sports are for, right?

Come what may, this offseason represents a defining moment for Ben Cherington and his future with the Pittsburgh Pirates. Whether he chooses to stay the course to attempt to prove it or pivot towards drastic moves to make big changes to attempt to keep his job, Cherington’s actions in the coming months will be under a microscope. His success, or lack thereof, may decide his fate as the GM.