Ben Cherington’s latest payroll promise has Pirates fans rolling their eyes

Reporting from the MLB general manager meetings earlier this week, FanSided's Robert Murray provided an update that sounds almost too good to be true: Not only will the Pittsburgh Pirates have "more flexibility" to add to their roster than they have in any of Ben Cherington's years with the club, but they also expect to explore both trades and free agency to upgrade the roster.

Pirates fans have heard this song before — and they know exactly how it ends. Ben Cherington’s claim that Pittsburgh has “more flexibility than we’ve had in other offseasons” sounds nice on paper, but for a fanbase conditioned by years of half-measures and false promises, it rings hollow for several reasons.

When Cherington says “flexibility,” he isn’t saying “money.” That word is intentionally vague — it could mean anything from room under the luxury tax (irrelevant for Pittsburgh) to having fewer long-term contracts (which they’ve always had). In practical terms, it usually means they can shuffle payroll around –– not that they’ll actually increase it.

Until ownership opens the checkbook — not just for extensions like Bryan Reynolds’, but for genuine free-agent impact players — “flexibility” is corporate camouflage for "status quo." Pirates fans have seen it used every offseason as a buzzword to justify bargain hunting.

Pirates fans won't believe Ben Cherington's "payroll flexibility" claim until they see it

Mark Feinsand of MLB.com did report that the Pirates are estimated to spend about $30-40 million to add to their payroll in 2026. But it's unclear whether that estimate accounts for arbitration raises or factors in the departures of Ke'Bryan Hayes, David Bednar and Isiah Kiner-Falefa from last season.

Still, the fact remains that since Cherington took over as GM in 2019, the Pirates have not signed a single multi-year free agent. Their total MLB payroll has stayed in the bottom five each year, and their biggest winter “additions” have been reclamation projects and short-term stopgaps rather than core pieces.

So when Cherington says they’ll “explore both trade and free agency,” fans hear: “We’ll window-shop in free agency, then trade a reliever for a bench bat.” The front office’s history simply doesn’t back up any bolder interpretation.

Even if Cherington wanted to push harder, the same obstacle remains — owner Bob Nutting’s unwillingness to spend real money. “Flexibility” under Nutting has always meant shaving costs, not expanding them. Fans know that as long as the owner refuses to reinvest profits into payroll, the GM can’t credibly promise a leap forward.

With Paul Skenes winning the Cy Young and Konnor Griffin emerging as the sport’s top prospect, this is the moment for the Pirates to spend. If Cherington truly believes in “building around a young core,” it’s time to prove it — not through more quotes about “flexibility,” but through an actual offseason statement (like adding a legitimate third baseman or outfield bat). Until that happens, skepticism isn’t cynicism — it’s earned experience.

Pirates fans have every reason to doubt Cherington’s “flexibility” rhetoric because it’s a rerun of every November platitude from the Nutting era — a promise of possibilities that rarely, if ever, materialize into real investment.