Ben Cherington enters his eighth season as Pittsburgh’s general manager in 2027, fresh off attaining a winning record for the first time in his tenure. The team finished with an 82-80 record in 2026, an 11-win improvement over the previous year.
With the GM Meetings in Las Vegas this week, the Pirates are beginning to look at ways to upgrade their roster once again.
“We believe whatever the record was, we know it wasn't good enough,” Cherington said on Tuesday. “I think we can look at it across the roster and be pretty open-minded about how we go about taking that next step.
“We've got a good foundation in place. We've got a lot of players already on the team that can be part of it, and we know we've got to get better. And so we can be pretty open-minded as to how to do that.”
Bringing back star second baseman Brandon Lowe through free agency could be a first step. The Pirates are still waiting on a decision from Lowe on the $23.15 million qualifying offer; the deadline to accept is next Tuesday.
Cherington noted that Pittsburgh must first let Lowe’s decision play out before determining how the club plans to pursue upgrading its roster. The Pirates have recently increased their interest in big-ticket free agents, going after Kyle Schwarber and Munetaka Murakami last offseason before signing Ryan O’Hearn to the largest deal for a free-agent hitter in franchise history.
“I don't feel like we're hamstrung or constrained,” Cherington said. “But it is a different offseason … there are different commitments on the books and a different arbitration class, and I think it will have some effect on how we approach getting better. But that part's not changing.”
The current roster is becoming more expensive each year with salary bumps due to players under contract (Bryan Reynolds and Mitch Keller), as well as increases coming for first-time arbitration-eligible players like Paul Skenes, Jared Jones, Nick Gonzales, Spencer Horwitz and Carmen Mlodzinski.
The result of Lowe’s decision will also impact the future infield dynamic. Pittsburgh has a solid core in the outfield, but adding to a young rotation and bullpen will be vital.
The Pirates are exploring options to improve left-handed pitching via free agency or trade, as first reported by The Athletic and confirmed by a source to MLB.com. Pittsburgh’s only current left-handed starting option is the inexperienced Hunter Barco. Out of the bullpen, Mason Montgomery will hold down the late innings, but Brandon Eisert and Evan Sisk are the only other southpaws with Gregory Soto hitting free agency.
When asked by MLB.com last week about the question of balancing lefties in a rotation, pitching coach Bill Murphy said he faced the same dilemma in Houston.
“For me, it just comes down to, you just want to have good pitching,” Murphy said. “I don't care if they throw righty or they throw lefty. They’ve got to be able to get out righties. They've got to be able to get out lefties.”
Cherington also expressed confidence that Skenes would bounce back from a down year by his Cy Young standards and confirmed MLB.com’s report last month of Mitch Keller being fully recovered from his Grade 3 right arm teres major muscle strain.
Cherington is bullish on what Pittsburgh’s pitching could look like in 2027.
“You look at 2026 and our total pitching performance, I think it's fair to say we gave up a few more runs than we thought we would and think we're capable of,” Cherington said. “We think we're capable of being better than that. I also think there's some things under the hood that suggest that maybe there's a little bit of bad luck in there because the strikeout rate and walk rates are really good.”