
The Pittsburgh Pirates have long been one of the least fruitful organizations in professional sports, and much of that has to do with the fact that they rarely open up their wallet.
Owner Bob Nutting's refusal to spend money over the years has prevented the Pirates from being able to take the next step, and it's the primary reason why there is so much speculation regarding Paul Skenes' future in Pittsburgh.
However, general manager Ben Cherington recently stated that the Pirates will be dedicated to trying to improve the roster this winter, which means actually going out and signing some bats to bolster an offense that was the worst in baseball in 2025.
But will Pittsburgh actually do it? Jim Riley of BALLCAP Sports has his doubts.
“I know there was talk out of the [GM] meetings about this team going out and addressing the run scoring and trying to improve the lineup there, but at the end of the day, I don’t think they’re going to get the green light from Bob Nutting to spend the money that is required," Riley said.
The Pirates currently rank 26th in the majors in payroll, and based on their history, it's hard to imagine them surging up the list anytime soon.

"I think they want to try to get the help that they need, but I don't know if it is going to be a significant enough piece," Riley added. "... I think ultimately, I think the fanbase will be disappointed this offseason. Feels like the desire is there, but the ability to execute on that desire ... I've got to see it happen first."
There are definitely some affordable avenues available for Pittsburgh this season, but another part of the problem is convincing players to actually sign with the Buccos.
Let's face it: the Pirates don't exactly have a rich history, so it may be difficult to sway veteran players to jump aboard. Pittsburgh may have to overspend in order to make that happen, and that seems rather unlikely.
The Pirates' best bet may be making some shrewd trades. They have been labeled as a potential destinations for outfielders Jarren Duran, Jo Adell and Taylor Ward, but whether or not they would actually be willing to part with the assets needed to get such a deal done remains to be seen.
Skenes made it clear after the season that he is expecting a more concerted effort from Pittsburgh this winter, but will the Bucs actually follow through? We'll see.