By now, Pittsburgh Pirates fans have learned to live in the land of “probably not.” Probably not signing a big free agent. Probably not keeping stars long-term. Probably not pushing all the chips in during a winnable window.
So when MLB insider Jeff Passan casually dropped that the Pirates were "in on" free agent slugger Kyle Schwarber — one of the most proven power bats of his generation — most fans reacted the same way:
“Sure. And I’m ‘in on’ owning a yacht.”
But now? Now it stings in a way only this organization could make possible.
Because while the Pirates were floating around these fantasyland Schwarber rumors, Schwarber himself went and dropped his own hint — that he might be interested in signing with his hometown Cincinnati Reds. A division rival. A team already trending up. A club whose ownership, while flawed, at least pretends to want to win.
Suddenly, those ridiculous Schwarber/Pirates rumors feel even worse.
Kyle Schwarber said he and his family will spend a lot of time back home in Middletown in the future.
— Charlie Clifford (@char_cliff) November 20, 2025
As the NL MVP runner-up gears up for free agency, he spoke with our @Porters_Videos about potential interest from his hometown Reds: pic.twitter.com/jvO1vsF1mZ
Kyle Schwarber to Pittsburgh rumors were always a fantasy, but Reds connection hurts more
Here’s the thing: Pirates fans knew they weren’t signing Schwarber. They know the payroll history. They know Bob Nutting’s track record. They know how a “rumor” becomes a “headline” becomes a “LOL, of course they didn’t do it."
But when you find out Schwarber might go to Cincinnati? Now, it’s not just a pipe dream that evaporates; it’s a pipe dream that comes back to punch you in the face.
The Reds signing Schwarber wouldn’t just be Pittsburgh missing out on a star. It would be the Pirates watching a division rival weaponize the kind of bat the Pirates refuse to pay for –– yet another example of the NL Central passing Pittsburgh in ambition.
If the Pirates had simply stayed quiet? If they’d avoided the “we’re in on Schwarber” posturing? None of this would sting. But they willingly stepped into this ring. They invited the comparison. They let fans dream — for 10 seconds, anyway — about real power in the lineup. They used the possibility of trying to sound aggressive instead of actually being aggressive.
Ben Cherington claims there’s “more flexibility" in the Pirates' budget. Insiders say the Pirates might spend $40 million. Ownership whispers big aspirations. Fans are told to believe. But Schwarber-to-Pittsburgh was never believable –– not because he's not a fit (he absolutely is), but because this organization refuses to play on that field.
Now, the fear is that the Pirates won’t just miss — they’ll watch a division rival get better while they sit out yet another bidding war.
The Reds have flaws, but at least they’re opportunistic. At least they try when a player makes sense. At least they act like a team that wants to climb. The Pirates? They act like a team trying to justify not climbing.
So yes –– Schwarber probably won’t end up in Pittsburgh. He probably never would have. But now that he’s potentially eyeing Cincinnati, it feels like the universe reminding Pirates fans of the cruelest truth: Even when Pittsburgh dreams big, someone else gets the payoff.
So, the Pirates didn't just lose Schwarber; they lost the illusion they could even try. Even if Schwarber doesn't end up in Cincinnati, he was never coming to Pittsburgh –– and the Pirates never gave him a reason to.
