The 2026 Pittsburgh Pirates are on the brink of being a special team, but their 50-47 record shows that they are a few pieces away from greatness. With a looming lockout going into the 2027 season, it is imperative that Ben Cherington get this deadline right to maximize the Paul Skenes era. Below are players I think the Pirates should target in tiers of “one can dream,” “plausible,” and “Get ‘Er done.”
One Can Dream
Tarik Skubal
It is no secret the Pirates desperately need pitching, particularly in the bullpen as they continue to lose games for the team. However, Skubal would be my number 1 target at the deadline for numerous reasons. I believe he can kill 2 birds with 1 stone in terms of helping the Bucs. The main reason to acquire Skubal is to immediately give the team the best 3-headed monster in baseball. A 5-game NLDS series feels much better if you have Skenes/Skubal/Ashcraft going. I also believe an elite starter will help alleviate the bullpen by making them pitch fewer innings. Here is my proposal to get half a season of Skubal:
Pirates Receive: Tarik Skubal
Tigers Receive: Edward Florentino, Jhostynxon Garcia, Reinold Navarro
Ernie Clement
The Pirates are hurting in terms of defense at 3rd base and need a solution at 2 infield positions if Brandon Lowe leaves town in the offseason. Ernie Clement can play both 2nd and 3rd and can play them at a high level defensively. With 2 years left of control, the Blue Jays would be hard-pressed to sell. There would be a bit of a logjam on the roster for playing time (it would make Jared Triolo a full-time bench player). However, Clement is an excellent short-term and long-term stopgap that would be very cheap to roster. He is another high-contact batting average type that would slot in well with the power-hungry, high-strikeout players on the team. Here is my proposal to get Clement in Pittsburgh:
Pirates Receive: Ernie Clement
Blue Jays Receive: Axiel Plaz, Wilber Dotel, Antwone Kelly
Plausible
Aroldis Chapman
With recent struggles from Gregory Soto and Mason Montgomery, the Pirates no longer have reliable lefty bullpen arms to turn to. While the Red Sox have roared back to be within striking distance of the playoffs in a weak AL, there is a good chance they are willing to chase value and sell off relief pitching. A Chapman reunion in Pittsburgh would make a lot of sense in terms of team needs, but the real question is if Bob Nutting will be comfortable taking on Chapman’s owed money for another year. Chapman has been elite this season, keeping his walk rate down and maintaining elite strikeout and ERA numbers. Here is my proposal for a season and a half of Chapman:
Pirates Receive: Aroldis Chapman
Red Sox Receive: Wyatt Sanford, Levi Sterling
Get ‘Er Done
Adrian Morejon
Morejon is my white whale for the deadline, as he’s been consistently one of the better relievers in the league without having his price tag inflated with gaudy save numbers. He would only be a rental, but he would immediately come in and be the best reliever on the team and someone the Pirates can count on to lockdown games. As the Padres free fall away from playoff contention they are increasingly more likely to become sellers. I think value wise Morejon is the guy you get instead of overpaying for Mason Miller. Here is my proposal for half a season of Morejon.
Pirates Receive: Adrian Morejon, Matt Waldron
Padres Receive: Rafael Flores Jr, Tony Blanco Jr
Luke Weaver
If the Pirates exit the deadline with Morejon and Weaver, they will have done amazing work to stabilize the backend of the bullpen. Weaver has been one of the few bright spots on the dumpster fire coming out of Flushing, striking out nearly 29% of batters and posting an ERA under 2. He also has an extra year of control, alleviating headaches for next season in terms of roster construction. He will be expensive, but he is also a reasonable target as the Mets will be one of the few true sellers at the deadline. Here is my proposal to get Weaver to Pittsburgh:
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