Pirates seek big upgrade after missing in pursuit of Schwarber (source)

ORLANDO, Fla. – It was a big swing in free agency, but alas, a whiff.

Kyle Schwarber is returning to the Phillies on a five-year, $150 million deal, a source told MLB.com. The Pirates were in the running for Schwarber this winter, offering him a four-year deal at $125 million, per a source.

Landing Schwarber always seemed like a long shot, but the offer the Pirates made was telling. The largest free-agent contract in team history is the three-year, $39 million deal Francisco Liriano signed during the 2014 offseason, so this offer was more than triple that deal in total dollars. All discussions this winter have centered around winning in 2026, and beating the eventual winning bid’s average annual value shows that there is money to spend and the Pirates are willing to be far more aggressive than they have in the past.

That’s good, because there are plenty of holes to fill on an offense that finished last in the Major Leagues in runs (583), home runs (117) and OPS (.655) in 2025.

“In a sort of perverse good way, our bar is such that we can improve in any number [of ways],” Ben Cherington said Monday at the Winter Meetings, when asked if there are traits he is looking for when acquiring hitters. “More on-base, more power, more contact. You name it, we need all of it. I think we need some combination of better depth. One through 18 position players, kind of what we have on the pitching side, so that there's that stiffer competition amongst the group, but also more certainty. We want both and are pursuing both.”

The most obvious needs for the Pirates’ offense are at third base and the outfield. Although they acquired Jhostynxon Garcia, the No. 85 prospect in baseball according to MLB Pipeline, from the Red Sox this month, the 22-year-old isn’t believed to be the definitive third outfielder for the club at this time.

Third base was always going to be a need after the Pirates traded Ke’Bryan Hayes to the Reds in July. They moved several controllable players at the Trade Deadline, including David Bednar and Bailey Falter, which did create some financial flexibility for this offseason, with the expectation being that they have $30 million-$40 million to spend. That could potentially increase if they trade Mitch Keller, who is due to make $16.5 million.

The Pirates have been quiet on the free agent market so far this winter, mostly waiting to see if Schwarber would accept their offer. Now, they’re going to have to pivot.

They have been connected to Jorge Polanco, one of the top infielders on the market, and are expected to have an offer on the table soon. While not a perfect fit in terms of positional need, he would be an upgrade in the infield, and the Pirates have some flexibility around the diamond thanks to Jared Triolo.

They also expect to be active on the trade front, where they still have starting pitching to deal. Though it’s perhaps not as pressing a need, the bullpen is also an area the Pirates would like to upgrade, getting another leverage arm and someone who can retire left-handed hitters, whether that’s a lefty or a righty with reverse splits.

Those are just some options in what has been a wide search for hitters, which Cherington believes will yield some bats.

"I am very confident we'll be able to execute between now and Spring Training,” Cherington said Monday. “I don't know when it will happen. I don't have a sense if it's going to happen in the next three days, next week or next month. Confident that we're going to be able to land some stuff that makes us feel better about the position player group and the depth of the lineup going into Spring Training. Believe that the best way to do that is to be engaged on as many fronts as possible. You chase 100 things, and three, four, five land. That's still the stage we're at."