The Pirates have taken plenty of heat for failing to build a real roster around Paul Skenes or even considering sending him to a contender. Moreover, their already-low payroll, which was projected to drop even further in 2026, hasn’t helped their reputation. But the narrative might finally be shifting.

Reportedly, the Pirates actually plan to spend on free agents, something they really haven’t done in years. Their most significant needs appear to be on the left side of the infield and in the corner-outfield spots. And yes, this is a team that hasn’t given a multi-year deal to a free-agent hitter since 2015, when they signed John Jaso for two years and $8 million.

Now, though, there’s word that a top free-agent DH is on their target list… A move that could be a real game-changer, especially with Skenes already anchoring the pitching staff.

“Pirates are in on free agent Kyle Schwarber, per Jeff Passan. Pittsburgh offered Josh Naylor at least $80 million before he re-signed with the Mariners,” Talkin’ Baseball reported.

Yes, you heard that right… The same Pirates, unwilling to go big in any offseason, are pursuing one of the top names from this free agency.

For the unversed, Pirates GM Ben Cherington said last week that he has “more financial flexibility than we’ve had in other offseasons I’ve been in Pittsburgh,” and it already seems to be showing.

The team has expressed early interest in a couple of the top bats on the free-agent market, including Kyle Schwarber. And to achieve that, the Pirates seem to be ready to put $135 million!!!

And honestly, why not? Schwarber is coming off a 56-HR season with the Phillies and blasted 187 home runs across his four years in Philadelphia before hitting free agency. Kyle Schwarber isn’t just another power bat. He’s one of the most accomplished postseason hitters of his generation and a proven middle-order anchor wherever he’s gone. His left-handed, pull-heavy power also fits PNC Park extremely well.

Also, he is the one who pushed Shohei Ohtani harder than anyone in the 2025 NL MVP race. If not for Ohtani’s two-way dominance, Schwarber’s 56-homer season would have made him the clear favorite.

This extra spending room for Pittsburgh exists partly because they shed salary at the trade deadline, moving players like Ke’Bryan Hayes and David Bednar, and that decision now looks justified. The Pirates already have an impressive young pitching core led by 2025 NL Cy Young winner Paul Skenes, but their offense was one of the league’s worst last season, ranking dead last in slugging (.350), OPS (.655), and home runs (117).

With Hayes, Bednar, and several arbitration pieces off the books, Pittsburgh entered the winter with one of MLB’s lowest future payroll commitments. Paired with a significant attendance and revenue boost from Skenes’ Rookie of the Year and Cy Young breakout, the front office finally had both the financial runway and competitive urgency to pursue a true middle-order star like Schwarber.

So now the big question is whether bringing in Schwarber could finally flip the script for Pittsburgh.

The Pirates’ direct challenge to the Red Sox

While the statement sounds more dramatic than what actually happened in reality in 2025, the offseason appears to be the same.

Well, it’s not just the Pirates in the mix for Schwarber — the Red Sox are firmly in the chase, too. Boston knows exactly what he brings, having seen him put up big numbers and instantly become a clubhouse favorite after arriving from the Nationals at the 2021 deadline.

And this time, their pursuit is driven by real urgency. With Rafael Devers gone and another playoff miss behind them, the Red Sox badly need a proven middle-order force.

Schwarber already thrived in Boston once, delivering power, patience, and presence, which makes bringing him back one of their top offseason priorities.

And now, with Rafael Devers in San Francisco, the Red Sox badly need another big bat in the heart of their order.

So, if Boston managed to bring Schwarber back and re-sign Alex Bregman, they’d arguably become the American League favorite in 2026, regardless of how the rotation shakes out.

But the Pirates aren’t making it easy. With their sudden renewed optimism and some financial breathing room after shedding salary, Pittsburgh is ready to go head-to-head with Boston in the race for Schwarber.