Pirates interested in Kyle Schwarber showed interest in Josh Naylor

Pirates GM Ben Cherington said last week that he “more [financial] flexibility than we have had in other low seasons. I’ve been to Pittsburghand subsequent reports indicated that Bucs ownership could approach the $40 million mark this winter with their spending plans. This willingness to spend money has translated into some early interest in two of the top players on the free agent market, as ESPN’s Jeff Passan reports what the Pirates are interested in Kyle Schwarberand was also interested in it Josh Naylor before Naylor re-signed with the Mariners.

The exact nature of the Bucs’ talks with Naylor was not specified, but Passan indicated the Pirates were willing to offer Naylor more than $78 million. This would have been, by a wide margin, the most expensive free agent deal in Pirates history. Francisco LirianoThe three-year, $39 million deal from December 2014 remains the biggest guarantee the perennially low-spending Buccos have ever given to a free agent.

Naylor rejoined the Mariners for five years and $92.5 million. Beyond just the money, there was enough mutual interest between Naylor and the M’s to continue their relationship, as evidenced by Naylor agreeing to a new deal so soon after the free agent market opened. Seattle appears well-positioned to continue to compete throughout Naylor’s tenure, so it would likely have taken a drastic overpayment from the Pirates to convince him to leave the Mariners for a Pittsburgh club that has endured seven consecutive losing seasons.

Along the same lines, Schwarber is expected to receive many offers from major market contenders, including his former team in Philadelphia. MLB Trade Rumors projects that Schwarber will receive a five-year contract worth $135 million even though he is entering his age-33 season and is essentially a DH player at this point in his career. Schwarber’s immense power, consistent production and reputation as a clubhouse leader will likely outweigh concerns about his age, and the Phillies (much like the Mariners with Naylor) are making it a priority to bring Schwarber back into the fold.

That said, the fact that Schwarber and Naylor are even mentioned in connection with the Pirates is an eye-opener, and perhaps an indication of how unusually aggressive Pittsburgh can be in its efforts to upgrade its lineup. While the Pirates were rebuilding for most of Cherington’s tenure, his final few offseasons saw the GM spread his limited spending power among multiple players, with the idea of ​​addressing different needs rather than executing a single major move. The tactic makes sense on paper, but in practice it hasn’t really worked as the Bucs have stayed below the .500 mark.

With this in mind, Pittsburgh may now be more open to adding a clear star to its lineup, even if it means stepping outside the team’s usual financial comfort zone. The absolute top of the free agent market (i.e Kyle Tucker or Bo Bichette) is still likely out of the question for the Pirates. But when Schwarber and Naylor are on the radar, players like it Cody Bellinger, Pete Alonso, Eugene Suarez, Kazuma Okamotoand any number of other available bats could now be within Pittsburgh’s spending range.

Bucs fans can be forgiven for adopting a “we’ll believe it when we see it” stance on the Pirates’ pursuit of big-name free agents. That said, Paul Skenes“The 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 guns was let down by a dismal offense in 2025, so adding hitting is the clear top priority on the team’s offseason checklist.

The general theory entering the winter was that Pittsburgh would again trade its stock of pitchers to obtain some much-needed hitting help. Cherington had already flatly rejected any possibility of Skenes being dealt, but it is conceivable that any of the less experienced arms could be dealt for an equally promising young bat. As for the Buccos’ more veteran pitchers: The Athletic’s Ken Rosenthal and Will Sammon reported that today Johan Oviedo attracts trade interests, 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 space for further moves. This could mean more exploration at the top end of the free agent market, or the Pirates could potentially 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 achieve this goal, although such an easy match isn’t a given on the trade front.

Just because the Pirates looked at Naylor doesn’t necessarily mean the team is unhappy with the incumbent first baseman Spencer Horwitzas Horwitz could be moved to DH if another first baseman were added. It could also mean that Pittsburgh looked more broadly at every top bat available, and figuring out the positional fit could come as an afterthought.

One position that probably won’t get much attention is shortstop, as a top prospect Connor Griffin expected to play in the Majors sometime in 2026. This could even be as soon as Opening Day, as Passan writes that “the Pirates are strongly considering giving money [Griffin]…the opportunity to win their shortstop job in the big league during Spring Training. It would be a bold promotion for a 19-year-old with just one year of professional ball under his belt, and Griffin’s resume includes 21 Double-A games and zero Triple-A games.

Still, Griffin is seen as perhaps the best prospect in baseball, and he’s looked so impressive in 2025 that he already appears to be on the verge of his MLB debut. By placing Griffin on the Opening Day roster and keeping him in the Majors through 2026, the Pirates could ultimately earn a bonus draft pick through the Prospect Promotion Incentive program should Griffin win Rookie of the Year honors or if he finishes in the top three in the NL MVP voting during his pre-arbitration years.