Plenty of questions surround the Pirates this offseason, including whether or not Andrew McCutchen is — or even should be — a part of their plans for the 2026 season.
McCutchen, who has expressed interest in playing an 18th major-league season, has signed a one-year contract with the Pirates in each of the last three years. He’s done so with the intention of helping lead the team to a playoff appearance for the first time since he last did so back in 2015.
Over the last few winters, it wasn’t a matter of if McCutchen would return. It was just a matter of when he would sign.
Now, after back-to-back 76-win seasons and a 71-91 output in 2025, there isn’t exactly a clear-cut answer surrounding McCutchen’s future with a franchise he has now spent 12 years with between two separate stints.
During the Winter Meetings in Orlando, Fla. this week, Ben Cherington was asked about how the Pirates intend to handle discussions with McCutchen, as they simultaneously work to improve their roster with offensive upgrades at other positions.
“Respect is the word I go to (with McCutchen),” Cherington said. “Respect him, certainly respect the career, the Pirates contribution, the contribution to baseball. His legacy is secure. So start with respect. And that leads to just dialogue, communicate. I think the big thing right now is we’ve got some work to do. We have some work to do and more to learn about what our team looks like. And I think as we work through that, continue to be respectful to him and share what we have, the information we have, and he will with us, I’m sure, and we’ll see where that takes us.”
While it seems there are pieces to the offseason puzzle that the Pirates must put into place before deciding if McCutchen fits into their plans for 2026, it’s not as if the 39-year-old is unworthy of consideration.
He’s not the same player he was during his first stint with the team when he was a five-time all-star (2011-15) a four-time Silver Slugger (2012-15), a Gold Glove Award winner (2012) and a National League Most Valuable Player (2013). But there’s still something left in the tank.
McCutchen led the Pirates in on-base percentage (.333) and walks (67), and ranked among the team leaders in just about every offensive category. He did, though, finish with career-low slugging percentage (.367) and OPS numbers (.700) while seeing his batting average dip below .240 for the fourth time in the last five years.
At some point this offseason, the Pirates — and McCutchen himself — have to make a decision. The organization is in a position where major upgrades are needed in terms of the lineup. They’ve already shown interest in and been connected to designated hitter options such as Kyle Schwarber, Josh Naylor and Ryan O’Hearn this winter, plus Bryan Reynolds seems like an internal option given his declining range and defensive metrics in right field.
Then, in the case of McCutchen, he’s in a position, at the latter stages of his career, where he wants to compete for a World Series ring. Does he truly believe that’s something he could do in Pittsburgh, or would it make more sense for both sides to move on?
A decision doesn’t have to be made anytime soon. There are other priorities and things can play out before McCutchen’s future is ultimately decided. But both sides eventually have to determine whether or not another year in Pittsburgh makes sense.
“The relationship between the Pirates and Andrew is important, and we want to do what we can to preserve that,” Cherington said. “And he has expressed that he’s interested in continuing to play. So we really respect that, too.”