The Pirates are averaging 73 wins per year since Paul Skenes joined the club, including a 71-91 finish to the 2025 campaign. With 4 years of control left in his rookie timeline, the pressure to build a contender should be boiling over internally. We’ll believe that when we see it however.

A Bright Spot
Pitching to sell. SP Mitch Keller was a name to watch this past deadline, and will certainly come up again this winter. Pittsburgh can benefit both in what they can receive in return for his services, but also in freeing up his $15.4M tax hit, and maybe taking a stab at free agency. Maybe.

A Big Concern
Scoring Runs. The Pirates were dead last in runs scored, home runs hit, and team OPS last season. While there isn’t one way to slice an onion, scoring runs seems to be something a good team should be good at doing.

Related Links
2026 Pirates Financials
MLB Offseason Guides

Pending Free Agents

McCutchen is a shell of what he used to be, and is tied to the franchise forever, but allowing him to move on to a contender this winter probably makes the most sense for both sides. Pittsburgh needs MLB-ready, everyday bats both on the field and on the bench next season. Pham is a perennial latch-on then trade free agent.

Arbitration-Eligibility

Bart fell back down to earth in 2025 after a mini-breakout campaign the year prior. Pittsburgh might be looking to see if Henry Davis can stick full-time in 2026, which may mean a release/trade for another catcher or two. As whole here though, this is a contributing group that accounts for less than $18M of projected tax next season.

Guaranteed Salary

Keller seems to be the big trade chip this winter, while getting Reynolds back on track at the top of the batting order will be a key to Pittsburgh’s quick turn-around. He’ll need 2-3 new, MLB-ready bats to protect him properly.

Team Tax Projections

Pittsburgh heads into the offseason with a projected $81M CBT payroll, affording them around $163M of space to work with. From a practicality standpoint, the Pirates are two offseasons away from getting serious about taking trade calls for Paul Skenes. The idea of winning with him has to begin today, no matter the cost.