Cherrington Penciled in As Pirates’ GM For 2026

I’m not the expert on the Pittsburgh Pirates. What I am is a fan of the team. This is plenty for me.

As MLB’s postseason is off and running, many teams are planning for spring training. However, before February arrives, the Winter Meetings will take place in Orlando on December 7 and 8. This is traditionally the time when team general managers engage in wheeling and dealing. Depending on how much ownership decides to allocate to player payroll, in most cases, this will determine which players a team will pursue.

Will the Pirates be raising payroll? I don’t know. Will Cherington and his staff be in hot pursuit of one or more legitimate bats? Don’t know. Will it be in Orlando that additions or subtractions to manager Don Kelly’s coaching staff get announced? Not a clue. You see, I’m clueless because I’m not employed by the Pirates, and Cherington isn’t calling my number for advice on any ideas that he is contemplating.

Being on the outside looking in, I know my role as a writer. I can make educated guesses on who and what I think may take place, but it’s all opinion. For me, getting to ask ballplayers about subjects that others aren’t showing interest in to pursue is my specialty. I enjoy speaking with coaches and others with the team, but not in uniform. There are many fascinating people with interesting stories to share.

It doesn’t matter to me if Cherington was going to be fired at the end of this past season. Not at all. I’m not the owner. The sun will rise tomorrow (especially here in Bradenton), and the Pirates’ front office is at work piecing together next season’s club. There are many talented “insiders” who are well plugged in on what may or may not be in the Pirates’ pipeline. I’m content with being a fan with a press credential. No politics necessary. What the team’s principal owner, Bob Nutting, decides on for next season is a given.

What I wouldn’t be qualified to do is label either Cherington or any other Pirates’ personnel a “dead man walking”. With the decision to bring back Kelly as manager, a well-deserved honor, and Cherington, who is under contract, I believe, for the next two seasons, it’s time to move on from beating this drum. My advice to those still harping about Cherington not being fired is to let it go. There are a million stories about the organization to search out and report on.

Looking in from a distance, some fans, media members, and others who are dwelling so deeply on how the Pirates could improve in 2026, my advice is to relax. Have some fun. The promise that spring training offers is nothing short of baseball excitement. Take in the moment. Before you realize it, the players of today could be future inductees to the Pirates’ Hall of Fame. Time flies. I know. Coming from the Cooperstown, N.Y. area, so many of the Hall of Famers, who were once young and whom I cheered on as a child at Shea Stadium, Yankee Stadium, and Doubleday Field during Hall of Fame Games, are now far older than they appear on their baseball cards.

Baseball is a game. Watch it being played instead of dissecting it and contemplating how it should be played. There are those in authority and those who can sit in the bleachers and observe. Life’s complicated at times. Pittsburgh Pirates baseball should be seen in its most simple form – a release from reality.

Go Bucs.