Ben Cherington Dishes On Pirates’ Offseason Goals And New Strategy

The Pittsburgh Pirates are ready to make some noise this offseason. After telling teams at last week’s GM meetings that they’re looking to spend more this winter, they reportedly targeted Josh Naylor before he re-signed with the Seattle Mariners and have been linked to Kyle Schwarber.

The Pirates appear to be acting more aggressively this offseason and with a greater sense of urgency. They apparently have some money to spend this winter and are looking to improve on a disappointing 2025 campaign, especially offensively.

Pittsburgh GM Ben Cherington recently spoke with MLB.com’s Alex Stumpf about the team’s goals and strategy for this pivotal offseason.

Cherington said the Pirates are still in the “information-gathering phase,” which makes sense given how early it is in the offseason. That said, “Cherington suspects Pittsburgh will dedicate an equal amount of attention towards trades and free agency this winter,” Stumpf writes.

That could entail the Pirates’ first multi-year free agent deal in nearly a decade, as they haven’t signed one since late 2016.

“It’s bound to happen,” Cherington said. “We have tried. It’s bound to happen. The odds have increased a little bit each offseason with the combination of the strength of our pitching — and the opportunity to win with that pitching foundation — and a little bit more flexibility. I think a combination of those two things gives it a better chance, but we’ll find out.”

Cherington has emphasized that he has more financial flexibility to work with than in years past, which should help Pittsburgh add some talent this winter. After building one of the best homegrown pitching staffs in baseball, the Pirates are now focused on bolstering their lineup.

“Bottom line is we want to add to our position-player group, and we’re going to explore all ways to do it,” Cherington said.

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