The turnaround hasn't happened yet, and it's easy to wonder if it ever will. The Pirates went 71-91 this season following 76-86 finishes in 2023 and 2024.
The standings indicate that the Pirates are going backward. That is especially true if you believe in Bill Parcells' school of thought, which says you are what your record says you are.
History suggests that the Pirates are a bad franchise. They have had 29 losing seasons in the last 33 years, haven't won a division title since 1992, and have not played in the World Series since beating the Baltimore Orioles in 1979.
Yet, the Pirates believe Cherington can lead them to a .500 record and beyond in 2026. Despite his lack of success, Cherington is under contract through 2027, and Pirates team president Travis Williams explained the organization's reasons for confidence in the GM on Monday, following a news conference to announce the extension of manager Don Kelly's contract.
"Our belief and expectation are that this team is a lot closer than our performance and our records would suggest," Williams said. Our goal is to win in 2026 and to make the playoffs. Period. Full stop. And we know that with that in mind, we need to build on the momentum that we've already built, that we already have moving forward. We have the best young pitching staff in all of baseball. We have a great core of young position players, and in addition to that, we have one of the best farm systems in baseball, the top prospect in baseball."
Indeed, the Pirates possess the game's best prospect in 19-year shortstop Konnor Griffin, who finished the season at Double-A Altoona. They also have a talented young pitching staff anchored by odds-on National League Cy Young Award favorite Paul Skenes.
Yet the Pirates desperately need to improve an offense that was last in MLB in scoring and home runs this year, among other categories. Otherwise, it will be more of the same in 2026.
"We know that we need to be better," Williams said.