The Pittsburgh Pirates are doing something this offseason that fans haven’t seen in a while - they’re opening up the checkbook. For a franchise long known for its tight spending habits, this winter has brought a noticeable shift in approach, and it’s turning heads across the league.
Let’s start with what they’ve already done. Pittsburgh was in on some big names early - designated hitter/outfielder Kyle Schwarber and first baseman Josh Naylor were both on their radar before ultimately signing with the Phillies and Mariners, respectively. And while the Pirates didn’t land those particular targets, their interest alone was a sign that the front office is thinking bigger.
Then came the signing of Ryan O’Hearn. The 32-year-old first baseman inked a two-year, $29 million deal - not only a solid addition to the lineup but also the first multiyear free-agent contract the Pirates have handed out since Ivan Nova’s three-year, $36 million deal back in 2016.
That’s nearly a decade without committing to a free agent beyond a single season. So yes, this feels different.
And they’re not done. Reports surfaced Wednesday linking the Pirates to left-hander Framber Valdez, one of the top starting pitchers still on the market. For a team that’s often sat out the higher end of free agency, this level of activity is a clear signal: the Pirates are no longer content to sit on the sidelines.
But while the spending spree is encouraging, it also brings a looming question into sharper focus - what’s the plan for Paul Skenes?
At just 23 years old, Skenes has already established himself as one of the most dominant pitchers in baseball. Since debuting in 2024, he’s been nothing short of electric.
A two-time All-Star, Skenes won NL Rookie of the Year in his debut season, finished third in Cy Young voting that same year, then captured the Cy Young outright in 2025. He even cracked the top 10 in NL MVP voting.
The numbers back it up: a 1.96 ERA, 0.948 WHIP, and 386 strikeouts over 320.2 innings. That’s ace-level dominance, full stop.
And here’s where things get interesting. Skenes is set to reach arbitration after the 2026 season, which means his salary is about to climb - significantly. For a team that’s historically been cautious with payroll, that could become a major inflection point.
According to a report from 93.7 FM The Fan’s Dan Zangrilli, the Pirates and Skenes began discussing a potential extension back in August. Since then, though, there hasn’t been much noise. No leaks, no updates, no indication of serious momentum.
That silence shouldn’t last. If the Pirates are serious about building a sustainable contender - and their recent moves suggest they might be - then locking up their franchise cornerstone has to be priority No.
- Skenes isn’t just a great pitcher; he’s the kind of player who changes the trajectory of an organization.
Every time he takes the mound, the Pirates have a real shot to win. That’s rare.
That’s valuable. That’s worth investing in.
And beyond the on-field impact, there’s a ripple effect. When a team shows its commitment to keeping elite talent, it sends a message to the rest of the league - and to future free agents.
Think about what happened in Toronto when Vladimir Guerrero Jr. signed long-term. That deal didn’t just lock in a superstar; it helped make the Blue Jays a more attractive destination for other top-tier talent.
The Pirates could follow that same blueprint. If they continue to pursue top free agents while also securing their homegrown stars, they’ll be in a position to compete - not just for one season, but for several.
So yes, it’s encouraging to see Pittsburgh spend. But the real test of their commitment to winning isn’t just about who they bring in - it’s about who they keep.
And in Paul Skenes, they’ve got a generational arm already in the building. Now it’s time to make sure he stays there.