The Pirates are selling this year, and there is no doubt about it. It makes sense for them to deal all their one-year guys and listen on a few guys that have a couple years remaining on their contracts. Ben Cherington's only goal at this deadline should be getting guys that can help Pittsburgh win in 2026 and beyond.
Adding players that are MLB ready may be difficult using only rentals, but there are a few other guys tenured beyond 2025 that could also be traded to help the mission. These three players that fit that criteria should remain in Pittsburgh, and the Pirates must avoid trading them if they want to contend in 2026.
These three Pirates must not be dealt at the 2025 MLB Trade Deadline.
David Bednar
David Bednar has finally returned to his All-Star self and has not allowed an earned run in his last 10 outings. He has just one year left on his contract before he hits free agency, so he should be the Pirates closer in 2026 as well, instead of being dealt when his value is back up.
Even though Bednar may be able to land the Pirates a quality prospect, they should think about thier 2026 plans and keep him. Having an elite closer at the level that Bednar is throwing right now may cost over $10 million a year. Bednar may be around $7 million for next season, so really, keeping a closer that is affordable for Pittsburgh and can be dominant like he has been since being recalled from Triple-A makes a lot of sense for this organization.
Bailey Falter
Just like Bednar, Bailey Falter has gained a lot of value on the trade market and is very cheap. His ERA sits at 3.36 right now and, as a middle to back-end kind of starter, that is excellent. Southpaws traditionally do well at PNC Park, and the Pirates do not have many in their farm system. Hunter Barco has done well and Anthony Solometo is hurt. There isn't much to work with beyond that tier, so keeping Falter makes a lot of sense.
Andrew Heaney is definitely going to be traded, too, so re-signing him doesn't seem likely, especially since his solid start to the season will make his salary go up in free agency. The rotation feels stable with guys like Paul Skenes, Mitch Keller, Jared Jones (sometime in 2026), Bubba Chandler, and Mike Burrows. Those are all right-handers, so throwing Falter in that mix would work out well for this team.
Dennis Santana
Lastly is Dennis Santana, who has been a staple in this bullpen since being claimed last summer. Like Bednar, he has been elite and is a cheap option as a closer. As a duo in 2026 with Bednar, they could be one of the most effective eighth and ninth inning men, all while being paid less than $10 million combined.
To be successful, the Pirates must upgrade their offense, and if they can get away with having Bednar and Santana for the pirce of $10 million or less, then they can spend more on players to improve the offense. Even though Santana could bring back a solid return, keeping him may be more valuable to the team's success in 2026.