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Offseason Outlook: Pittsburgh Pirates

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By | at October 14, 2026 2:48pm CDT

The Pirates took a step forward in 2026 but still missed the playoffs for an 11th consecutive season. They’re now set for a notable set of salary increases in arbitration and could lose one of the best bats available this winter to free agency.

Guaranteed Contracts

Other Financial Commitments

2027 financial commitments: $57.5MM
Total long-term commitments: $256.5MM through 2032

Arbitration-Eligible Players (service time in parentheses; salary projections via MLBTR contributor Matt Swartz)

Free Agents

Although the Bucs once again fell shy of the playoffs, there were undeniable positive strides for the organization in 2026. An already strong rotation looks even more formidable following the performances from some key young arms. Konnor Griffin, the game’s top prospect, debuted at 19 years of age and held his own (but missed a good chunk of time on the injured list). The revolving door at catcher hasn’t necessarily halted but could be trending in that direction. And while an 82-80 record isn’t especially exciting in a vacuum, it marks an 11-game improvement over 2025 and stands as the Pirates’ first winning season since 2018 (when they also won 82 games).

Those trendlines, it seems, will be enough to get general manager Ben Cherington another crack at building the Pirates’ first postseason team since 2015. Cherington is under contract through the 2027 season, and while owner Bob Nutting hasn’t definitively declared he’ll finish that contract out, the GM himself indicated late in the season that all of his conversations with Nutting have focused on how they can improve the club for 2027 and beyond. Manager Don Kelly, meanwhile, was only in his first full season on the job in 2026. He’s expected back, too.

Much of Kelly’s roster in 2027 will look the same. Griffin will return at shortstop. Spencer Horwitz and Ryan O’Hearn will have first base and designated hitter covered. O’Hearn will probably see some time in the outfield corners, but the outfield has Bryan Reynolds, Oneil Cruz and breakout slugger Esmerlyn Valdez, with former top prospect Jhostynxon Garcia still on the periphery of the group. Endy Rodriguez looked to be breaking out behind the plate before hip surgery ended his season. Nick Gonzales had a career-best season at the hot corner and can handle that position or slide over to second base, depending on what happens with the team’s most notable free agent: Brandon Lowe.

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