Teams that would make the best offseason trade partners with the Pittsburgh Pirates

With the World Series now over, MLB teams can move on and focus on the upcoming offseason. The Pittsburgh Pirates need to be active this fall and winter. There’s too much talent on the 40-man roster not to capitalize and make some impact moves this offseason.

The Pirates should have plenty of opportunities to add to and streamline the roster, aiming at winning more than 76 games, the unfortunate total they've reached in each of the last two seasons. They have a ton of pitching talent, but which teams would make the best potential trade partners for the Bucs?

3 teams who Pirates can trade pitching talent to this offseason

Boston Red Sox

One team that may be on the lookout for starting pitching is the Boston Red Sox. The Sox are coming off an 81-81 season. They, like the Pirates, had a dismal second half of the season. The Red Sox only went 37-41 after the start of July. Their pitching definitely let them down as part of those second-half struggles.

Red Sox arms owned a 4.49 ERA, 4.55 FIP, and 1.33 WHIP from July 1 onward. They have a decent core of pitching, as they had five starters make double-digit starts, and only one was older than 30. Granted, none were younger than 25, either.

Still, they also do not have much in the way of pitching depth in the upper levels of the minor leagues, even after acquiring Quinn Priester. Developing pitching is Craig Breslow's specialty, and it's time for him to really get to work.

Both MLB Pipeline and Baseball America only list two pitching prospects among the Red Sox’s top ten prospects and none in their top five. Their top eight prospects on Pipeline are position players, and their first seven on BA are also position players. Another thing many note is that they have an overabundance of left-handed batters.

Another area in which the Red Sox could use some depth is behind the plate. Connor Wong is coming off a solid season, but one that only looks nice on the surface, as he had a poor second half and some worrying underlying numbers. Former Pirates first-round pick Reese McGuire served as their backup catcher this season, and he is now a free agent. Deadline acquisition Danny Jansen is also now a bat for hire.

The Red Sox, meanwhile, have some position players that they could trade. Triston Casas would make a great fit for the Pirates, assuming the Red Sox would be willing to trade the 2023 Rookie of the Year candidate. Masataka Yoshida would also be a good option at DH/LF, though his contract is hefty. They’d likely be the first names the Red Sox would consider moving, making room for top prospect Roman Anthony in the lineup.

Baltimore Orioles

The Baltimore Orioles failed to improve upon a 101-win season from 2023. They still had a good season, winning 91 games, but they went from having the third-most wins in baseball heading into July to winning just two more games than the Pirates after that, eventually getting swept by the Kansas City Royals in the Wild Card series.

Many of those second-half struggles stemmed from their pitching. As a unit, they had a 4.50 ERA, 4.16 FIP, and 1.33 WHIP from July through the end of the season. The Orioles only had one starter last year who made double-digit starts, had an ERA+ of over 100, and is under control for next season. That’s 34-year-old Albert Suarez. They did acquire Zach Eflin at the deadline, who is under control for next year, and will have a healthy Grayson Rodriguez look to continue to improve his game. However, Corbin Burnes is a free agent, and Kyle Bradish underwent Tommy John surgery in June, which likely eliminates him for a good portion, if not all, of 2025.

The Orioles could use another MLB-ready or near-MLB-ready starting option, especially given they do not have many in their system. Both MLB Pipeline and Baseball America only list three pitching prospects among their top 10. Their top pitching prospect is Chayce McDermott, who had a good season at Triple-A but is their only top ten pitching prospect to have played above High-A.

Meanwhile, they could look to move some of their young position player talent. Four of their top 10 prospects on Pipeline are outfield prospects. Two of their outfield spots are taken up by potential Rookie of the Year winner Colton Cowser and stalwart Cedric Mullins. Anthony Santander is a free agent, but Heston Kjerstad showed off some potential in his brief MLB sample size and looks like he could take over right field, if he isn’t traded.

They could also look to move a player who already has Major League experience, like Ryan Mouncastle. The Orioles’ top prospects are Coby Mayo and Samuel Basallo. Both can play first base, and Basallo would have a hard time breaking into the Major Leagues as a full-time catcher, given Adley Rutschman's presence. Certainly something to think about, as the Orioles approach a pivotal offseason of their window.