Pirates Offseason Plans: What to Expect in 2026 (2026)

Get ready, Pirates fans, because the team’s offseason moves are far from over—and they’re aiming to shake things up big time. But here’s where it gets controversial: while many expected a focus on outfield additions, General Manager Ben Cherington has hinted at a surprising shift toward bolstering the left side of the infield instead. Could this be the game-changing strategy the Pirates need? Let’s dive in.

Cherington recently revealed the team’s ambitious plans: “Ideally, we’d strengthen both our starting rotation and bullpen, while also adding at least one more position player.” That position player is likely to be an infielder, with Jared Triolo—who impressed in the final months of the 2025 season—poised to take on third base or shortstop. Nick Gonzales is another shortstop contender, and Cherington teased a “really good younger prospect we’re excited about,” though details remain under wraps. And this is the part most people miss: the Pirates have also been quietly circling free-agent third basemen Eugenio Suárez and Yoán Moncada, adding another layer of intrigue to their infield strategy.

On the pitching front, the Pirates have a solid foundation with Paul Skenes, Mitch Keller, Braxton Ashcraft, and top prospect Bubba Chandler. However, only Skenes and Keller have logged 140 innings in a season, leaving room for another starter. Here’s where opinions might clash: the team has been in talks with free agents Jose Quintana and Tyler Anderson, both left-handed veterans who could bring much-needed experience to the rotation. But is relying on older arms the right move for a team eyeing long-term success? Jared Jones, who dazzled in his 2024 debut before undergoing elbow surgery, is expected to return in 2026, adding another wildcard to the mix.

As the Pirates continue to reshape their roster, one thing’s clear: this offseason is anything but ordinary. What do you think? Are the Pirates making the right moves, or are they overlooking key areas? Let us know in the comments—we’re all ears!

Excited for the 2026 season? Start planning your trips to PNC Park now: https://www.mlb.com/pirates/tickets?affiliateId=mlbcomarticle-inline-linkpit. And if you loved this deep dive, check out SiriusXM MLB Network Radio for more insider insights—get 3 months free at www.siriusxm.com/mlbnr.

Pirates Offseason Plans: What to Expect in 2026 (2026)
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