What’s Driving Pirates’ Surprising New Offseason Approach?

The Pittsburgh Pirates have been acting a bit differently this offseason than in years past, already pursuing Josh Naylor and Kyle Schwarber in the early days of free agency. This marks a major departure from past offseasons for the Pirates, who haven’t generated this much buzz in years.

Pittsburgh has signaled a willingness to spend more this winter, and several motivating factors could be in play.

One is that the Pirates have struggled on the field. They’ve endured seven straight losing seasons and haven’t made the playoffs since 2015, so being more aggressive in free agency could help them improve and contend for the postseason next year.

Pittsburgh’s attendance has suffered as a result, dropping by nearly 200,000 fans from 2024 to 2025 — an 11 percent decrease. That’s a concerning trend given that MLB attendance was up overall this year.

The Pirates may also be driven to put a better team around Paul Skenes. Despite having arguably the best pitcher in baseball, they’ve finished last in the NL Central in both of his first two seasons. If they continue to sputter, they risk alienating him and increase the likelihood that he demands a trade or leaves in free agency.

According to MLB agent Seth Levinson, there could also be an economic reason for Pittsburgh’s new approach, which may be impacting the Miami Marlins and other small-market teams as well.

“There is a possibility of a fight among clubs over revenue sharing, with the smaller markets seeing a greater contribution,” Levinson told The Athletic. “The payors (large-market clubs) will argue that insufficient revenue-sharing funds are being spent on player acquisition. Hence, it wouldn’t be a surprise if the smaller markets compete for talent in the free-agent market to convince the payors that they are committed to putting a better product on the field.”

Regardless of their reasons, the Pirates are making things more exciting for their fans this winter and could be on the verge of a major signing.

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