Meet the Pittsburgh Pirates: Baseball's Most Dysfunctional Organization

On paper, the Pittsburgh Pirates should be ecstatic. Paul Skenes just delivered one of the most dominant seasons baseball has seen in decades, winning the Cy Young and immediately establishing himself as a top-three player in the sport. He’s overpowering hitters and commanding the zone at an insane pace, and he is giving Pittsburgh a legitimate chance to win every time he takes the mound.

Players like this don’t fall into organizations’ laps often - especially not Pittsburgh’s.

But instead of treating Skenes like the franchise-altering superstar he is, the Pirates are raising a much bigger, much more troubling question: do they actually plan to build around him?

A Payroll Moving in the Wrong Direction

According to Noah Hiles of the Pittsburgh Post-Gazette, the Pirates’ payroll might actually decrease this year. Not level out. Not increase slightly. Decrease.

For a team boasting a Cy Young winner entering his prime, it’s almost unthinkable. Most franchises would view this as the perfect time to invest, push forward, and surround their ace with legitimate support. The Pirates, instead, are coasting as if they’re terrified of the idea of upward momentum. There doesn't seem to be any plans for a major move, and there is no sense of urgency going into this offseason - a familiar sight Pittsburgh fans have seen over the last 3 decades.

The False Promise of “Spending More”

The front office has hinted that they may “take on more spending” this offseason. Normally, that would be a positive sign - until you hear what it might actually mean.

The phrase "yet to be determined" keeps surfacing, and that kind of ambiguity is rarely encouraging. There’s a growing concern that “spending more” won’t be about improving the team at all, but rather taking on bad contracts from other teams in exchange for mediocre prospects. This behavior is consistent with the Pirates over the last 30 years, and for their fans and Skenes, it's a slap in the face. Instead of adding proven talent or building a better roster, the team seems more interested in absorbing dead money that won’t help them win games.

A Generational Talent With No Real Support

Skenes is the type of pitcher you build a decade-long contender around: elite stuff, elite mindset, elite results. He’s the kind of ace who changes everything for a franchise.

But none of that matters if the Pirates keep surrounding him with incomplete lineups, below-average depth, and a front office that treats winning like an optional expense.

Skenes has given Pittsburgh a golden window. It’s up to the Pirates to do something with it. But right now, all signs point to them wasting it.