Pirates Skipper Could be Fighting for Job, But is it Fair?

As the Pittsburgh Pirates continue to deal with some of the adversity that they've faced over the 2026 campaign, there are many ways that they can right the ship. For one, the Pirates have a lot of questions to answer this offseason, and a lot of it probably starts with Don Kelly and Ben Cherington. 

At the end of the day, Cherington hasn't made the playoffs in a long time, and Kelly, as a new manager, didn't always push the right buttons this past season. I don't want to blame either of them too much, since other factors are at play, including ownership not spending as much as it needs to.

It's unfortunate that Kelly and Cherington have to deal with some other things, but as long as ownership doesn't plan on spending a whole lot, this is what the Pirates are going to be. 

I would even go as far as to say that they could bring in some of the best general managers and managers in Major League Baseball to run things, and not everything would go as planned if they don't spend money.

It'll be interesting to see what direction they go in, but one writer believes that if they can get back to .500 and have a winning season while competing for a playoff spot over the final few weeks of the season, it's possible they could be back for another year.

“The Pittsburgh Pirates are probably goners with respect to reaching their first MLB postseason since 2015. They entered Thursday action 5.5 games back of Arizona for the final wild-card spot and had just a 1.5% chance of advancing, according to Fangraphs.

“The club might yet be able to save its general manager’s job, though. If manager Don Kelly and Co. can slip over the .500 mark to complete a winning season for the first time since 2018, then his boss, Ben Cherington, can still credibly point to progress toward another step in 2027 after six consecutive losing campaigns to start his tenure since his late 2019 hiring,” Adam Bittner wrote.

I personally don't think it would be the right idea to move on from Cherington and Kelly at the moment, definitely not Kelly. I can see the argument for moving on from Cherington, but I think he deserves some grace because he has to push buttons due to the lack of resources.