The Pittsburgh Pirates finished the 2026 season with an 82-80 record, staying in the playoff race until the final weeks of the year.
While the starting rotation is mostly set with right-handers Paul Skenes, Braxton Ashcraft, Jared Jones, Bubba Chandler, and Mitch Keller, general manager Ben Cherington indicated the front office is keeping an open mind about upgrades.
“We have a roster that’s pretty solid. How do we upgrade it? This offseason, that’s a little less specific to a single position and more where are the opportunities?” Cherington said at Major League Baseball’s general manager meetings in Las Vegas, as reported by the Pittsburgh Post-Gazette.
Despite keeping broad options open, the Pirates are actively targeting left-handed pitching. Sources told the Pittsburgh Post-Gazette that the team is trawling the left-handed reliever market, while remaining open to a left-handed starter or a swingman southpaw if the fit is right.
This market interest stems partly from roster composition, as top left-handed setup man Gregory Soto is a free agent. That leaves Brandon Eisert and Evan Sisk as lefty complements to Mason Montgomery, alongside former top-100 prospect Hunter Barco and Connor Wietgrefe ahead of a likely 2027 debut.
Nearly half of all at-bats in 2026 were taken by left-handed hitters—the highest mark in baseball's modern era since 1961—showing a league-wide trend toward southpaw counters.
Mitch Keller enters the winter following a 2026 campaign cut short by a right shoulder injury that landed him on the injured list in August. Cherington addressed questions regarding Keller’s All-Star potential versus potential trade flexibility.
“If there’s ways to make the team better through the rotation, then we’re going to pursue that,” Cherington said, adding that “there’s nothing that’s out of bounds.”
Cherington also expressed confidence in Keller’s recovery and upcoming workload for 2027.
“At the same time, we know what Mitch is capable of. Best outcome for him, best outcome for the Pirates, is he comes in and he’s clearly one of those guys we’re counting on 32 times a year. I’m betting that’ll be the outcome that we get,” Cherington said.
Re-signing free agent Brandon Lowe remains a top priority for the franchise after his strong performance last season. Cherington said that trades may provide the best avenue for improvement while preserving financial flexibility to retain Lowe.
The front office also aims to structure the 2027 roster so that Ryan O’Hearn primarily plays first base and designated hitter, minimizing outfield duty for O’Hearn. Meanwhile, young contributors like Esmerlyn Valdez and Rafael Flores Jr. received praise, though Cherington cautioned that Valdez has “some earning to do” before securing an everyday role.
Ahead of the Nov. 20 non-tender deadline, sources indicate the Pirates plan to tender contracts to the vast majority of their 11 arbitration-eligible players. The lone exception could be outfielder Akil Baddoo, who was claimed off waivers from the Milwaukee Brewers on November 2 and is projected by MLB Trade Rumors to receive $1.3 million.
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