Pirates insider's offseason roadmap to upgrade Pittsburgh is more of the same unless this changes

The Pittsburgh Pirates enter the 2025-26 offseason with the same desperate need to upgrade the offense that they had last year (are we even a little bit surprised?).

There are certainly ways for the Pirates to add bats, from free agency to trades, and Jason Mackey of the Pittsburgh Post-Gazette recently laid out several of those options in an offseason roadmap for the Pirates' front office. Among them include trading for Brandon Lowe or Jordan Westburg and signing upcoming free agents like Harrison Bader or Max Kepler.

All sound like great starting points. But a credible plan to upgrade the Pirates only exists if ownership — specifically Bob Nutting — allows spending that reflects a team trying to win, not just exist. Without that, every trade or free-agent idea is just window dressing for a franchise that refuses to take the next step.

Pirates insider's offseason roadmap to upgrade Pittsburgh is more of the same unless they increase payroll

At the end of the day, the Pirates’ financial ceiling dictates every move. Even the most creative general manager can’t build a playoff-caliber roster if the budget caps him at the bottom of MLB spending. When your payroll sits near $70 million (or less), there’s simply no room to add a legitimate, middle-of-the-order bat, retain productive veterans or strengthen depth with proven role players.

A realistic offseason roadmap requires flexibility – something the Pirates have never allowed Ben Cherington to operate with. Without it, every “plan” starts from a place of artificial scarcity.

Free agency is simply not an option on a bargain-bin budget. Without payroll growth, the Pirates’ free-agent targets will remain limited to bounce-back candidates (who almost never pan out), one-year stopgaps and low-cost veterans trying to revive their careers. Meanwhile, the types of players who could actually change the team’s trajectory all cost real money. You can’t patch every hole with “value signings” and expect sustained success.

Even if the Pirates wanted to go the trade route instead of free agency to upgrade their offense, that involves more than giving up prospects. A trade for an established hitter usually comes with an $8-15 million salary hit – and if you’re not willing to pay market rates, your trade options are limited to struggling players or post-prime veterans. That’s not how you build a contender.

Raising payroll isn’t just about buying talent; it’s about changing the organizational mindset. It signals to fans, players, and the rest of MLB that the Pirates are finally serious about competing. Until that happens, any “offseason roadmap” is just theoretical – a wish list written under false financial pretenses.