Pirates GM Ben Cherington said last week that he had “more [financial] flexibility than we’ve had in other offseasons I’ve been in Pittsburgh,” and subsequent reports indicated that Bucs ownership could approach the $40MM mark with their spending plans this winter. This willingness to spend has translated to some early interest in two of the best hitters on the free agent market, as ESPN’s Jeff Passan reports that the Pirates have interest in Kyle Schwarber, and also had interest in Josh Naylor before Naylor re-signed with the Mariners.
The exact nature of the Bucs’ talks with Naylor weren’t specified, yet Passan indicated that the Pirates were prepared to offer Naylor more than $78MM. This would’ve been, by a wide margin, the priciest free agent deal in Pirates history. Francisco Liriano’s three-year, $39MM deal from December 2014 remains the biggest guarantee the perennially low-spending Buccos have ever given to a free agent.
Naylor re-upped with the Mariners for five years and $92.5MM. Beyond just the money, there was plenty of mutual interest between Naylor and the M’s in continuing their relationship, as evidenced by the fact that Naylor agreed to a new deal so soon after the free agent market opened. Seattle looks well-positioned to keep contending throughout Naylor’s tenure, so it likely would’ve taken a drastic overpay from the Pirates to convince him to leave the Mariners for a Pittsburgh club that has struggled through seven straight losing seasons.
Along these same lines, Schwarber is expected to receive plenty of offers from big-market contenders, including his former team in Philadelphia. MLB Trade Rumors projects Schwarber to receive a five-year, $135MM contract, even though he is entering his age-33 season and is essentially a DH-only player at this point in his career. Schwarber’s huge power, consistent production, and reputation as a clubhouse leader will very likely outweigh concerns about his age, and the Phillies (like the Mariners with Naylor) are prioritizing bringing Schwarber back into the fold.
This being said, the fact that Schwarber and Naylor are even being mentioned in connection to the Pirates is eye-opening, and perhaps indicative of how uncharacteristically aggressive Pittsburgh may be in trying to upgrade its lineup. While the Pirates have been rebuilding for the bulk of Cherington’s tenure, his last couple of offseasons have seen the GM spread out his limited spending capacity over multiple players, with the idea of addressing several needs rather than making one single big strike. The tactic makes sense on paper, but it hasn’t really worked in practice, as the Bucs have remained under the .500 mark.
With this in mind, Pittsburgh might now be more open to adding one clear-cut star bat to its lineup, even if it means going outside the team’s usual financial comfort zone. The very top of the free agent hitting market (i.e. Kyle Tucker or Bo Bichette) is likely still out of the question for the Pirates. But, if Schwarber and Naylor are on the radar, players like Cody Bellinger, Pete Alonso, Eugenio Suarez, Kazuma Okamoto, and any number of other available bats could now conceivably be within Pittsburgh’s spending range.
Bucs fans can be forgiven for taking a “we’ll believe it when we see it” stance on the Pirates’ pursuit of major free agents. That said, Paul Skenes’ immediate impact as arguably baseball’s best pitcher has created more pressure on the team to return to contention while Skenes is still under team control. Skenes and the Pirates’ collection of promising young arms was let down by a dismal offense in 2025, so adding hitting is the obvious top priority on the team’s offseason checklist.
The common theory going into the winter was that Pittsburgh was again going to trade from its stockpile of hurlers to obtain some much-needed hitting help. Cherington had already flatly shot down any possibility of Skenes being dealt, but conceivably any of the less-experienced arms could be dealt for an equally promising young bat. As for the Buccos’ more seasoned pitchers, the Athletic’s Ken Rosenthal and Will Sammon reported today that Johan Oviedo is drawing trade interest, and Mitch Keller has been mentioned in trade rumors for months.
Keller is also the Pirates’ second-highest paid player, so dealing the right-hander would free up more payroll room for further moves. This could mean more exploration at the higher end of the free agent market, or the Pirates could conceivably take on some salary in a trade for a more expensive hitter. Trading Keller for a similarly-priced hitter would be the smoothest way to accomplish this goal, though such an easy match isn’t obvious on the trade front.
The fact that the Pirates were looking at Naylor doesn’t necessarily mean that the team isn’t satisfied with incumbent first baseman Spencer Horwitz, as Horwitz could be moved to DH in the event that another first baseman was added. It also could mean that Pittsburgh was more broadly looking at any available top bat, and figuring out the positional fit can come after the fact.
One position that probably won’t receive much attention is shortstop, as top prospect Konnor Griffin is expected to be in the majors at some point in 2026. This could even be as early as Opening Day, as Passan writes that “the Pirates are strongly considering giving [Griffin]…the opportunity to win their big league shortstop job” in Spring Training. It would be a bold promotion for a 19-year-old who has only one year of pro ball under his belt, and Griffin’s resume consists of 21 Double-A games and zero Triple-A games.
Nevertheless, Griffin is viewed as perhaps the best prospect in baseball, and he looked so impressive in 2025 that he already appears to be on the verge of his MLB debut. Putting Griffin on the Opening Day roster and keeping him in the majors throughout 2026 could eventually earn the Pirates a bonus draft pick via the Prospect Promotion Incentive program, should Griffin win Rookie of the Year honors, or if he has a top-three finish in NL MVP voting during his pre-arbitration years.
