It is not a secret—Pittsburgh Pirates owner Bob Nutting has been synonymous with frugality. After all, their payroll is lean, the free-agent splurges have been rare, and the multiyear contracts for hitters are almost unheard of. However, it seems like the wave of change is here—and it starts with Kyle Schwarber.

Jeff Passan from ESPN, in fact, pitched Pittsburgh as the surprising suitor for the 32-year-old slugger. He is fresh off a 56-home run, 132-RBI season with the Philadelphia Phillies. And this is a huge change from Nutting’s ways because the org hasn’t committed to a big free agent bat since 2015! This chase would mean a multiyear deal and a serious chunk of change—at least $30-$40 million in a new payroll at minimum.

And Mark Feinsand and Bob Nightengale both reported that the Pirates are expected to add that amount of millions to the payroll to work with. GM Ben Cherington has been clear-cut—change is needed, and they are ready to bring it.

“We need to win more games, and believe we’ll have flexibility to pursue some things in free agency and trades… We need to add to the offense, and we’ll be disappointed if we don’t,” Cherington said. Well, the Pirates’ pitching core is led by none other than Paul Skenes, but their offense is among the worst in baseball.

For now, Kyle Schwarber fits the Pirates’ blueprint perfectly—from elite power to consistent production—and he brings that veteran leadership. His left-handed swing would play nicely at PNC Park, too, where the right field foul pole is slightly closer than at Citizens Bank. But even then, getting him won’t be cheap or easy, given that they will face tough competition from the Phillies, Red Sox, Mets, Blue Jays, and Reds.

And it’s not just one example with Schwarber that highlights the team’s changing ways. The Pirates explored Josh Naylor, too, apparently, before he re-signed with the Mariners. So right now, the Pirates do want to spend like a contender.

Even then, fans can be skeptical, and it is understandable; they remember years of promising players being traded or underutilized. The revenue-sharing dollars are being stashed and then reinvested, and the management seems more concerned about the profits than about the wins. Even then, given Skenes is anchoring a young rotation and is a franchise cornerstone, Pittsburgh might be ready to take the financial leap they need to.

But how can the Pittsburgh Pirates really add $30 million AVV?

Last off-season, the Pittsburgh Pirates didn’t even spend close to $30 million, and even then, their payroll ticked up from 2024. Not by much—just under $90 million—but that’s with arbitration settlements factored in. The team estimated payroll now sits around $64 million. So how could the Pirates really add $30 million AAV without repeating past mistakes? Well, if they approach this winter like the last one, they will be in trouble.

Back in 2024, the Pirates went all in for the short-term deals. Aroldis Chapman ($10.5M), Martin Perez ($8M), Andrew McCutchen ($5M), Michael A. Taylor ($4.5M), Rowdy Tellez ($3.2M), and Yasmani Grandal ($2.5M).

The total is 433.6 million across one-year contracts, and factor in the Mitch Keller extension, too. Sure, it got them competitive for all of one second, but the approach is not sustainable. But this off-season, the plan has to be different, and they can’t hand out their biggest contract to pitchers. One name that’s entering the conversation is Jorge Polanco. 

MLB Trade Rumors projected a three-year $42 million contract that’s $14 million per year—a price that feels hefty for Pittsburgh but seems well worth it. He brings power; he hit 26 home runs in 2025, and he is consistent—so he could give the boost to the lineup that the team so desperately needs.

Polanco could also complement the young stars like Oneil Cruz and Spencer Horwitz. It is for sure uncharacteristic for a franchise that’s been so frugal for so long to go above and beyond to spend, but even then, given that the Pittsburgh Pirates’ heads have themselves taken the stance to change things, maybe things will be different this time.