Pittsburgh Pirates fans have seen this movie before. Actually, we’ve lived through the sequels, the prequels, the gritty reboot and the straight-to-DVD spinoff. Every winter, someone in the national media leaks that Pittsburgh is “in” on a marquee free agent, and every winter the Pirates step aside and say, “Oh no, you go ahead, we insist.”
So when Ken Rosenthal reports that the Pirates made a four-year offer “almost certainly” worth at least $100 million to Kyle Schwarber, fans don’t know whether to cheer… or check for hidden cameras. Because yes, that is real, actual money. That would’ve shattered the franchise record for a contract given to an external free agent. And yes, it suggests the Pirates can operate like a big-league operation when they feel like pulling up a chair to the grownups' table.
But let’s be brutally honest: Pirates fans are conditioned to treat these leaks like Bigfoot sightings. Intriguing? Sure. Encouraging? Maybe. Conclusive evidence that Bob Nutting has suddenly transformed into Steve Cohen overnight? Absolutely not.
Because until someone actually signs on the dotted line—multi-year, guaranteed money, not a one-year flyer or a waiver claim—this is all noise. And Pirates fans have ears ringing with fifteen years of noise.
The Pittsburgh Pirates have made an offer to Kyle Schwarber, per @Ken_Rosenthal
— SleeperMLB (@SleeperMLB) December 8, 2025
The offer is for four years and “almost certainly” worth more than $100 million pic.twitter.com/fvQshlo1NM
Pirates' reported offer to Kyle Schwarber sounds more like face-saving PR than real ambition
Let’s talk about the “offer.” On paper, four years and $100+ million to Schwarber sounds like a franchise-altering shift. It sounds like ambition. It sounds like the kind of move a team makes when it realizes it has Paul Skenes for only so many team-controlled seasons.
But you know what it also sounds like? A perfect way to say, “Look! We tried!” after yet another free agent got away. Because if we’re keeping score, this exact pattern already happened — literally weeks ago — with Josh Naylor.
The Pirates were reportedly “in” on Naylor. He was a perfect fit: left-handed thump, heart-of-the-order production, still in his prime. But he signed with the Seattle Mariners… and then it came out that the Pirates never actually made him a formal offer.
“In on Naylor” turned into “interested in Naylor” turned into “thought about Naylor,” which is always code for “no, we didn’t actually spend anything.” And now, suddenly, days later, we get the Schwarber report. A splashy dollar figure. A clear implication that the Pirates tried. A narrative-shifting headline.
But the beauty (for ownership) is this: it doesn’t matter whether Schwarber was never coming here. It doesn’t matter whether the Pirates knew they were a “long shot” from the start. Making the offer costs them nothing unless the player actually accepts it—and big-market clubs do this all the time.
For Pittsburgh, though, floating a nine-figure offer almost feels like the point. It allows them to say, “See? We’re serious buyers!” Except… no one signs. No one ever signs.
Pirates fans aren’t unreasonable. They’re not demanding a $350 million superstar. The ask is simple: sign –– just one –– real, legitimate, multi-year free agent. Break the seal. End the drought. Show you’re doing more than trying to win the PR battle at the Winter Meetings.
At some point, interest needs to become action. You don’t get a parade for a bid. You don’t get wins for a rumor. You don’t get fans back by almost spending money. You only get credit when you actually do it.
The offer to Schwarber is either a sign that the Pirates are truly ready to spend, a convenient headline to cover the fact that they never offered Naylor anything, or the classic playbook of floating a big number you know won't be accepted. Whichever of those is true, it doesn't change the real question: When will the Pirates finally sign a free agent to a multi-year deal that matters?
Fans don’t want to hear that the Pirates “tried” anymore. They want to see someone wearing black and gold at an introductory press conference. Until then, the skepticism isn't cynicism –– it's self-preservation.
Pirates fans want to believe. They desperately want this team to take advantage of the Skenes window, to build a real lineup around Bryan Reynolds and Oneil Cruz, and to prove that competitive windows actually matter in Pittsburgh. But until the Pirates close a deal—any deal—worth more than spare change, the Schwarber story will feel like just another winter tale told to make the faithful quiet down.
Talk is cheap. Rumors are free. Actual spending? That’s the part Pittsburgh hasn’t done yet.
