Pirates’ Offseason Offers Raise Eyebrows, Not Expectations
The Pittsburgh Pirates made some noise during the Winter Meetings - but not the kind that echoes through the league. Despite being linked to several high-profile free agents, including Kyle Schwarber and Josh Naylor, the buzz around the Bucs quickly fizzled once details of their offers emerged. According to league insiders, those offers were more smoke than fire.
Pittsburgh reportedly put a four-year, $125 million deal on the table for Schwarber and offered Naylor five years at $80 million. On paper, those numbers might seem aggressive for a team not known for opening the checkbook. But in reality, they weren’t enough to seriously shift the conversation - or the players’ interest.
Here’s the issue: if you’re a team like Pittsburgh, coming off a 71-91 season and riding a decade-long playoff drought, you’re not just competing with money - you’re competing with winning cultures, postseason opportunities, and market appeal. To lure away players entrenched in contending environments, you don’t just match offers.
You blow them away. That’s how the Nationals landed Jayson Werth.
That’s how the Tigers brought in Magglio Ordóñez and Iván Rodríguez. You pay a premium for relevance.
In this case, the Pirates didn’t. The suggested “real” offers - something in the ballpark of six years and $180-200 million for Schwarber, and six years, $120 million for Naylor - would’ve at least made agents pause.
Instead, the Pirates’ bids felt like a gesture, not a pursuit. A way to say, “See?
We tried,” without ever seriously entering the race.
A Familiar Pattern in Pittsburgh
If this all sounds familiar to Pirates fans, it’s because it is. The franchise has long been synonymous with conservative spending.
Since Bob Nutting became the principal owner in 2007, Pittsburgh has ranked in the bottom five in Opening Day payroll in 16 of 19 seasons. Their last multi-year deal for a position player in free agency?
Outfielder John Jaso for two years, $8 million - nearly a decade ago. Their last multi-year free agent deal of any kind came in 2016, when they signed Iván Nova for three years, $26 million.
This winter, there was hope that things might change. Talk of increased spending, rumors linking the team to big bats like Schwarber, Naylor, and even Pete Alonso - it all hinted at a potential shift in strategy.
But so far, the results have been more of the same. No splashy signings.
No seismic trades. Just familiar frustration.
And it’s not just about missing out on names - it’s about the optics. When a team with one of the league’s lowest payrolls makes headlines for being “in the mix” for marquee players, only to fall short again and again, it starts to feel performative. Offers that aren’t truly competitive don’t move the needle - they just move the narrative.
Where Do the Pirates Go From Here?
The Pirates’ 2025 campaign ended with them at the bottom of the NL Central, posting the fifth-worst record in baseball. It marked their 10th straight year without a postseason appearance and their seventh consecutive losing season - streaks that trail only the Los Angeles Angels in terms of futility.
That kind of track record doesn’t attract free agents. It repels them.
And unless the Pirates are willing to pay a premium to overcome that perception, they’ll keep watching talent choose other destinations. The front office can say the right things.
Ownership can hint at change. But until Pittsburgh becomes the highest bidder for a top-tier player - and actually lands him - the rest of the league won’t take them seriously.
And neither will the fans.
The Pirates have been linked to several big names this offseason, but so far, none have signed on the dotted line. That’s not just a missed opportunity - it’s a missed message.
This team needs offensive help, and they need it now. But unless the approach changes - not just in dollars, but in intent - it’s hard to see the Pirates breaking out of this cycle.
For now, it’s business as usual in Pittsburgh. And that’s exactly the problem.