The Pittsburgh Pirates haven’t exactly been known for opening the checkbook in recent years, but as we gear up for the 2026 season, there’s a noticeable shift in tone-and maybe even in ambition. No, they’re not suddenly spending like the Dodgers, Yankees, or Mets, but they’re also not sitting quietly in the corner of the hot stove season anymore. With a generational talent in Paul Skenes anchoring their rotation, the Pirates are showing signs they’re ready to capitalize on their window.
Let’s start with the headline move: Pittsburgh is bringing in former Orioles DH Ryan O’Hearn on a two-year, $29 million deal. For most clubs, that’s a solid mid-tier signing.
For the Pirates? It’s a statement.
This is their first multiyear free-agent deal since 2016-a stretch that speaks volumes about the franchise’s approach over the past decade. That last round of multiyear signings came when the team was fresh off a run of three straight postseason appearances.
Since then, it’s been a long, slow slide into irrelevance, with only a few short-lived respites.
But this offseason feels different. Alongside O’Hearn, Pittsburgh also traded for All-Star second baseman Brandon Lowe and outfield prospect Jhostynxon Garcia.
They added some bullpen firepower with a one-year deal for lefty reliever Gregory Soto. These aren’t headline-grabbing, blockbuster moves, but they’re the kind of smart, targeted additions that can raise a team’s floor-and maybe even its ceiling.
O’Hearn, in particular, is a strong fit for a Pirates team that desperately needed thump in the lineup. Last season, Pittsburgh ranked dead last in the majors in home runs (117), slugging percentage (.350), and OPS (.655).
That’s not just bad-it’s historically bad. O’Hearn brings a level of offensive consistency the Pirates have sorely lacked.
He slashed .281/.366/.437 with 17 home runs and 63 RBIs across time with the Orioles and Padres last season, earning his first career All-Star nod thanks to a strong first half in Baltimore.
Lowe, meanwhile, brings proven pop from the second base position and a veteran presence to a lineup that’s been short on both. He’s the kind of player who can not only produce but also help set a tone in the clubhouse-something that matters for a young team trying to turn the corner.
And while Soto had his ups and downs last year, he still brings high-leverage experience and a power arm to a bullpen that needs more swing-and-miss stuff. In a division where margins are often razor-thin, having a reliable bullpen can be the difference between playing meaningful baseball in September or packing it in by mid-August.
Of course, the Pirates didn’t land every target. They reportedly made a run at slugger Kyle Schwarber, trying to pry him away from the Phillies, but he opted to stay put. Still, the fact that Pittsburgh was even in the conversation for a bat of that caliber says something about how they’re approaching this offseason.
The numbers don’t lie-this franchise hasn’t posted a winning record since 2018, and even with Skenes dominating on the mound in 2025, they still finished just 71-91. But now, with a Cy Young winner leading the rotation, a couple of All-Star-caliber bats joining the lineup, and a front office showing real signs of engagement, there’s finally a sense that the Pirates are trying to build something sustainable.
No one’s confusing this roster with a juggernaut just yet. But for the first time in a long time, the Pirates are acting like a team that wants to compete-and that’s a big win in itself.