It's the MLB offseason, which is traditionally the time Bob Nutting and Ben Cherington slumber. However, Pirates fans and even players are holding the front office to the fire after another wasted season. Paul Skenes had a Cy Young-caliber campaign, and Pittsburgh owns one of the best pitching staffs in baseball. None of it mattered.
Skenes and the Pirates clubhouse have made their feelings known. As Nutting does most winters, he claims he's open to spending more on the on-field product. I'll believe it when I see it. Nutting and Cherington have long said they're committed to building a winner, and that there are many ways to achieve just that. One of those solutions is not, however, sitting on their hands and hoping cheap, young talent can outplay their potential. It should also not be to take on expensive contracts other teams don't want for a reason.
Ken Rosenthal of The Athletic dropped a nugget from the MLB GM Meetings that should give Pirates fans some hope, but not too much. Per Rosenthal, the Pirates (and Marlins) want to spend in free agency and via trade, taking on deals that other teams have deemed too expensive.
The Marlins and Pirates are telling agents they'd like to be aggressive and spend a little bit, says @Ken_Rosenthal.
— Foul Territory (@FoulTerritoryTV) November 11, 2025
"That can be in free agency, or it can be in the matter of taking on salaries in trades." pic.twitter.com/R5aAqrIVa2
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The Pirates offseason plan might not be what they claim
There's always a chance the Pirates listened to their players' exit interviews, and the comments made in the media to Noah Hiles of the Pittsburgh Post-Gazette (more on that shortly), and decided to change course. However, in an interview with FanSided, Hiles admitted last month that he wouldn't be surprised if the Pirates payroll went down, rather than up.
"I don’t expect payroll to be much higher, if at all. I wouldn’t even be shocked if it was lower on opening day. Revenue wasn’t what they thought it would be in 2025, and this owner isn’t spending more to fix it. Whatever money they do have to work with must go toward the outfield and third base. Bats. Slugging. Those two things are the focus," Hiles said at the time.
Again, Hiles answered those questions at the end of the season. Nutting is notoriously cheap, and the team struggled to sell seats and merch last season. If their revenue dipped, then it'd be on Nutting and his $1.1 billion net worth to put some money into the team, for a change. I cannot stress enough how little good faith Nutting has in the city of Pittsburgh, and it's why anything he says (or leaks) to the media should be taken with a grain of salt the size of Mt. Washington.
Who could the Pirates target if they're (actually) willing to spend money?
I (again) do not believe the Pirates here. This is an organization who literally threw some of its fans' prized possessions into a dumpster (see: Bucco Bricks fiasco), replaced the Roberto Clemente logo with a Surfside advertisement, and has just one winning season in the last 10 years. Prior to 2013, they went 20 straight seasons with a losing record. This franchise is abysmal, and I applaud any and all fans who have survived that stretch. They deserve more, and it shouldn't come in the form of other teams' bad contracts, or a free-agent reach or two.
If the Pirates are willing to spend, they must sure up the lineup. Nolan Arenado is available and on one of the worst contracts in baseball. Could the Cardinals trade him to a division rival with a prospect attached? It's doubtful, as Arenado would have to waive his no-trade clause. As far as free agents go, keeping Tommy Pham around would be a nice start. The Pirates also shouldn't let Andrew McCutchen walk, if they can avoid it.
In free agency, they could take a swing at Rhys Hoskins, who should have a decent market but be relatively affordable by Pirates standards. Eugenio Suarez would be a massive addition, but let's not kid ourselves, Nutting would have to take out a second mortgage to afford him. Why not Kiké Hernandez, who has plenty of postseason experience and is a classic glue guy who could keep this team together through tough stretches? Gleyber Torres just had a bounce-back season for the Tigers. If his price comes down at all, the Pirates could sign him to a multiyear deal, as their current starting second baseman is...Nick Yorke!
Why none of this will keep Paul Skenes around
We appreciate the effort, assuming it's even sincere to begin with, but adding a nickel and dime to the payroll here and there won't be enough to keep Skenes around beyond his contract end date. The good news for Pirates fans is that Skenes is under contract through 2030, and affordable via arbitration for quite some time. Assuming Cherington doesn't actually trade him — a ridiculous rumor for any organization not from Pittsburgh that surfaced last July — the Pirates will have plenty of chances to build around him. He'll also get more frustrated with each subsequent winter that goes by without the Pirates actually doing that.
In many ways, Skenes and Pirates fans have a lot in common. Pirates fans are among the most loyal in baseball. Skenes is one of the best pitchers in the sport. Both are hungry for a winner and will be left with an empty stomach unless Nutting opens his wallet for a change. I'll leave you with this sentiment from Hiles, who answered my question regarding how the Pirates could win back their fans.
"Overall, the only thing that fixes this is winning. This year was a disaster in all areas. The first day of the offseason was equally bad. Fans are more upset than ever, which is truly saying something. They want to see a winner, and don’t believe that can happen if the Pirates continue this same approach they’ve had for years, which looks to be their plan again in 2026," Hiles said.
Winning changes everything. If Nutting and Cherington truly want to be revered in this city, it will not come in the form of incremental payroll adjustments. Postseason success is the only language Yinzers speak, and it's been far too long since the baseball franchise lived up to that expectation.