Even when the Pittsburgh Pirates don't do anything, they wind up taking an L. In the wake of another brutally disappointing trade deadline, just about the only thing Pittsburgh has to focus on is trying to convince ace Paul Skenes to sign a long-term extension. And to the team's credit, they seem to be making an effort to do just that, having reportedly approached Skenes' camp in recent days.
But unfortunately, it seems like those efforts have approximately zero chance of bearing fruit. Convincing Skenes to push back his free agency for the sake of a team that refuses to pay for a competitive roster around him was already being described as "a longshot, uphill battle" ... and that's before the Boston Red Sox inked Roman Anthony to an extension of their own on Wednesday afternoon.
BREAKING: Outfielder Roman Anthony and the Boston Red Sox are finalizing an eight-year, $130 million contract extension, sources tell ESPN. The deal, which is pending a physical, includes a club option and will keep Anthony under team control through 2034.
— Jeff Passan (@JeffPassan) August 6, 2025
Per ESPN's Jeff Passan, the star rookie has agreed to an eight-year, $130 million extension, one that will buy out four years of his free agency and could climb as high as $230 million if certain escalators are reached. It's a great deal for the Red Sox, who lock up a player who already looks like a budding superstar at a price that might seem risky now but could wind up being a massive bargain in short order. It's also devastating news for Pirates fans, who now have a better idea of just how unlikely it is that Bob Nutting matches Skenes' asking price.
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Roman Anthony extension is just one more sign that Paul Skenes isn't long for Pittsburgh
Anthony is a very, very exciting player, a former top prospect who hasn't missed a beat since coming to the Majors back in June. But Skenes is the better and more proven player right now, and he plays a more important and lucrative position. So if Anthony is getting $130 million over eight years, the price for Skenes would figure to be something north of $200 million. And if you think the Pirates are going to pay that price, I've got a bridge in Pittsburgh to sell you.
As a friendly reminder, this is a franchise which hasn't cracked a $100 million payroll since 2017, a borderline criminal streak that has cost Pittsburgh dearly on the field. There's a very good chance that Nutting's miserly ways have already convinced Skenes not to sign away his future for any price, but even if he's still open to sticking around, what would make anyone think that Nutting could afford it?
Assuming Pittsburgh's payroll continues to hover around $90 million a year, around a quarter of that number would be taken up by a Skenes extension. There's simply no evidence to suggest that the Pirates would find that workable, no matter how badly fans wish it were otherwise. It's only a matter of time before these contract talks inevitably break down, and from there, the trade speculation will only ramp up. You know, unless Rob Manfred finally forces Nutting to sell the team to someone who actually cares.