MLB will have its eyes on the Boston Red Sox this offseason because of their needs at the top of the free agent market, but also the high likelihood of them trading from their major league roster.
The trade market is a fascinating part of this offseason for Sox fans. The team has an outfield surplus that it will likely trade from to improve other parts of the squad. The advantageous part of trading one of their outfielders is that they are all on inexpensive contracts, meaning that any team around the league looking to improve won't have any qualms about adding them for financial reasons.
One surprising team may be finding itself in talks with the Red Sox. The Pittsburgh Pirates are looking to add this winter and are reportedly willing to increase their payroll. For the first time in years, it seems like the Pirates are looking to try and make a push for the playoffs, and that will come with some additions to the roster.
The Boston Globe's Pete Abraham suggested that Boston and Pittsburgh match up well for a trade (subscription required). Since they're seemingly willing to spend this season, given their links to top free agents like Kyle Schwarber, they may also be open to some bigger trades.
The Pittsburgh Pirates are expected to add at least $30 million in payroll for the 2026 season, per @BNightengale
— Just Baseball (@JustBB_Media) November 14, 2025
Baseball officials with access to their finances say they are one of MLB’s most profitable teams. pic.twitter.com/HsRAfoYC9m
Can the Red Sox and Pirates make a clear need-for-need swap?
PNC Park in Pittsburgh is much friendlier to left-handed hitters, something the Sox are overloaded with. The Pirates also have an abundance of pitchers, something the Sox are looking for.
While Paul Skenes is off the table in Pittsburgh, the Sox could pivot to one of Jared Jones, Mitch Keller, or potentially Bubba Chandler. While none are the number two starter the Sox are looking for, at least at the moment, they would all be floor raisers for the bottom half of the rotation.
As far as a possible return, any of Jarren Duran, Wilyer Abreu, or even Marcelo Mayer could headline a package. All three lefties would be immediate upgrades for the Pirates. If the Pirates are also looking to add to their payroll, they may also be willing to take on Masataka Yoshida. According to FanGraphs Roster Resource, Pittsburgh's opening day DH at the moment would be Endy Rodriguez, who had a negative fWAR last season. Yoshida would certainly be an upgrade there.
While the two sides aren't a perfect match, the Sox would have some pieces the Pirates would be interested in. The two front offices have worked together before, when they swapped Nick Yorke and Quinn Priester at the 2024 trade deadline. Going off of Abraham's analysis, the two teams could certainly swing a trade that would benefit both parties.