This story was excerpted from Alex Stumpf’s Pirates Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
This is shaping up to be the most important offseason the Pirates have had in some time. Paul Skenes, the 2025 National League Cy Young Award winner, is entering his final year of pre-arbitration control, and Pittsburgh boasts one of the best young rotations in the game. The club needs an offense that can support that staff.
It looks like the Bucs should be able to take a couple swings at improving that lineup. MLB.com’s Mark Feinsand listed them as a potential surprise spender this offseason, reporting that they could spend between $30 million and $40 million. General manager Ben Cherington confirmed to Feinsand at last week’s General Managers Meetings that the team does have some room to work.
“We need to win more games and believe we have some flexibility to pursue some things in free agency and trades,” Cherington told Feinsand. “We aim to add to the offense and will be disappointed if we don’t. What that looks like, we don’t know. We’ll pursue lots of stuff, for sure.”
The Pirates have some flexibility and plenty of areas that need to be addressed. How can they do that?
WHERE SHOULD THEY LOOK?
Cherington suspects Pittsburgh will dedicate an equal amount of attention towards trades and free agency this winter. The club always explores options on both sides, but Cherington hinted last year that he thought the Pirates would be more active on the trade front. They did make one big deal, acquiring Spencer Horwitz, but there wasn’t much of a trade market, hence the pivot to free agents come January.
With free agency seemingly being more of an option now, there is a question worth addressing. Can they sign someone to a multiyear deal? The Pirates haven’t signed a hitter to a multiyear free-agent deal since John Jaso nearly a decade ago, and they haven’t signed a free agent to a multiyear deal since Iván Nova in December of 2016.
Of course, the Pirates have tried to sign free agents to longer deals over Cherington’s time as general manager, but if they are able to communicate with players and agents that they are open to multiyear deals, it should expand the pool of players they could potentially sign.
“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.
“Bottom line is we want to add to our position-player group, and we’re going to explore all ways to do it.”
WHAT’S ON THE SHOPPING LIST?
Cherington said the Pirates are still in the “information-gathering phase,” so it’s still early to identify specific names. But we can paint with some broad brushstrokes for now.
The Pirates’ greatest areas of need are in the outfield and left side of the infield. Depending on what happens with Andrew McCutchen, getting another bat for a designated hitter would help, too.
They have pitching prospects (and Mitch Keller) to make a trade, while teams like the Angels and Red Sox seem in position to trade outfielders for pitching. Could that be a good pairing?
WHAT ABOUT KONNOR?
There’s a wild card when it comes to planning out the left side of the infield: Konnor Griffin, MLB Pipeline’s No. 1 prospect in baseball. It doesn’t make sense to sign multiple infielders to multiyear deals if he’s going to be on the 2026 radar.
So, is he? Cherington admitted they “have to think about it” when considering their offseason plans.
“Typically you would see a player like that and think they would benefit from some more time at the upper levels of the Minor Leagues,” Cherington said. “We haven’t made a decision. The great thing about Konnor is, when we put a challenge in front of him, he’s met that challenge. To some degree, we’re going to keep doing that, and to some degree, he’s going to tell us a little bit about what the timeline is.”
