If Paul Skenes and Kyle Schwarber share a dugout during the 2025 season, it’ll almost certainly only be during July’s All-Star Game. Despite the Pittsburgh Pirates reportedly uncharacteristically trying to land Schwarber, the All-Star slugger opted to stay put and re-sign with the Philadelphia Phillies during the Winter Meetings.
We always try to give credit where credit is due, and the Pirates should be applauded for reportedly offering Schwarber a four-year contract worth roughly $125 million. Considering that the Pirates haven’t signed a free agent to a multi-year deal in nearly 10 years, the idea that they were open to signing Schwarber is notable, even if said pursuit failed.
Paul Skenes is still watching the Pirates after striking out on Kyle Schwarber
But just because the Pirates struck out on their top target doesn’t mean that they should stay put and get back to hunting through the bargain bin. For the sake of baseball and any hope that Skenes will eventually sign an extension with the Pirates, it’s time for Ben Cherington to use his Schwarber chase as a stepping stone to further upgrade their roster.
The worst possible thing that the Pirates could do after being spurned by Schwarber is to shrug and say, “Well, we tried to sign a free agent, and look what happened.” Schwarber turns 33 next spring and wanted to stay with an organization that he’s called home for four years and one where he’s been immensely successful. Even a penny-pinching club like the Pirates understands that such moves aren’t personal. It’s business, always business.
Where should Pirates turn after missing on Kyle Schwarber?
None of this is to say that the Pirates need to go all-in and open up the books to give a combined $250 million to Alex Bregman, Cody Bellinger, or Framber Valdez. At the same time, there are plenty of free agents worth seeking out and potentially signing to multi-year contracts.
Zac Gallen
We’ve repeatedly highlighted former Arizona Diamondbacks starting pitcher Zac Gallen as a possible bounce-back candidate, and it’s not unrealistic to suggest that he could command a two-year deal. Gallen was linked to the rival Chicago Cubs earlier this winter, but that deal has yet to be completed. The Pirates can outspend contending teams for Gallen, even on a one-year deal that could offer Pittsburgh the opportunity to flip the former NL Cy Young candidate at the trade deadline.
Willi Castro
Although Willi Castro posted -0.2 bWAR in 120 games for the Minnesota Twins and Chicago Cubs last season, -0.5 of that came over his 34 games with the Cubs. In other words, we won't let an awful two months change the narrative about Castro being a useful utilityman. Castro has played every position but catcher and first — and yes, that includes pitcher — since debuting with the Detroit Tigers in 2019.
Miguel Andujar
What about a reunion with Miguel Andujar, who previously played for the Pirates in 2022 and 2023? Andujar hit a career-high .318 with 10 home runs, 44 RBIs, and a .822 OPS in nearly 350 plate appearances with the Athletics and Reds last season. He would certainly be an excellent fit in the Pirates' lineup.
There's nothing wrong with Pirates making a small-market move
There is a misconception among baseball fans that teams like the Pirates, Rays, and Rockies hurt the sport by not spending in free agency, though that’s only part of the problem. Those clubs aren’t aggressive outside of when they’re trading their best players before they become free agents.
By no means is Andujar a name that will immediately turn heads, though that doesn’t erase the fact that he’s grown into a solid DH option entering his age-31 season. Suppose the Pirates sign Andujar to a contract in the ballpark of two years and $16 million. That’s the type of move Skenes and baseball fans should want to see an organization like the Pirates make in the offseason; it’s relatively risk-free, and it shows that a rebuilding team is at least somewhat interested in creating the impression that they care about winning.
No, we don’t think the Pirates are going to compete for the World Series next season. In fact, I’m still skeptical that they’ll come anywhere close to a .500 record. Nonetheless, I’m hoping — and I’m sure that I’m not alone — that the Pirates will prove that their quest to sign Schwarber was the start of a trend rather than an aberration.