Pirates' offseason spending may not be as aggressive as it looks

On the surface, this winter looks like the long-awaited pivot for the Pittsburgh Pirates. The transaction log is busy, the 40-man roster is churning, and general manager Ben Cherington has been more vocal than usual about wanting to be “active” in free agency. Names are coming in and out of the organization, and it’s easy to look at the flurry and assume the Pirates are finally ready to spend like a team that expects to contend in the near future.

But look a little closer, and the aggressive veneer starts to crack. A lot of what the Pirates are doing right now is about cleaning up the margins and clearing future money off the books, not suddenly behaving like a big-market heavyweight. Payroll for 2026 is already projected to land well below where it sat in 2025, thanks in large part to prominent departures and a lack of expensive commitments replacing them. If this front office is planning a true step forward with the checkbook, it hasn’t fully shown up yet — and until it does, it’s fair to wonder whether this offseason will end up looking more like another careful reset than a real spending spree.

What the Pirates’ roster purge really says about their offseason plan

The latest round of roster shuffling drives the point home. In one swoop, the Pirates pushed outfielders Alexander Canario and Ronny Simón, plus right-handers Colin Holderman and Dauri Moreta, off the 40-man via DFA. None of them are franchise pillars, but they’re the kind of serviceable big leaguers or depth options contenders usually like to keep around. 

At the same time, infielder Cam Devanney was cut loose to chase an opportunity with the Hanshin Tigers in Japan’s NPB. On paper, it’s routine front-office maintenance. Put alongside a shrinking payroll, though, it reads less like a team adding layers and more like one quietly shaving down the edges.

That pattern extends beyond the back end of the roster. The Pirates’ financial flexibility is growing in large part because they’ve moved on from higher-priced deals, including established, previously core pieces like Ke’Bryan Hayes and David Bednar. 

Between arbitration cases falling away and guaranteed salaries coming off the books, the club’s projected obligations for 2026 are significantly lighter than they were a year ago. That creates room to add, sure, but it also raises a question that Pittsburgh fans know too well: will that space be used to push the payroll into a new tier, or simply reset it to a lower level and call it “flexibility”?

Cherington has suggested that the Pirates will be more active in the free-agent market this offseason, and technically, that can be true without this turning into a real spending breakout. We’ve already seen their name floated around bigger bats. There were rumblings they were in on Josh Naylor before he landed with the Mariners, and there’s still reported interest in Kyle Schwarber. But interest and actual offers are two very different things. 

“More active” can still just mean a deeper class of one-year deals, a higher volume of mid-tier signings, or creative short-term bets that look good on a spreadsheet, but don’t really move the competitive window on their own. If the savings from letting go of key contributors and veteran contracts mostly get funneled into patchwork additions instead of true middle-of-the-order upgrades, the overall payroll can land comfortably below last season’s figure while the front office points to the number of signings as proof of ambition. It’s a classic small-market balancing act: talk big, stay in the rumor mill, do just enough to look busy, but not enough to fundamentally change the team’s financial identity.

That’s why, despite the headlines and transaction buzz, the Pirates’ offseason may not be as aggressive as it first appears. Roster shuffling, DFAs, and overseas releases make for an active transaction wire, but activity and investment are not the same thing.