The Boston Red Sox have not had the greatest year, despite expectations from the fanbase. Injuries have plagued the roster with more than 10 injuries since the beginning of the season, and most of them have been their pitchers. It's one of their biggest holes this season, and it'll have to come with sacrifices.
GM Craig Breslow believes that they can "bolster" at the deadline and believes heavily in this team...perhaps maybe too much. But regardless, if he thinks this way and wants to commit to the bit, he'll have to pay a pretty penny for it. Is it foolish? Probably. But give Breslow some credit for wanting to fill holes on the team.
Their biggest holes on the team are threefold: They need a true power hitter in the lineup, they need an excellent secondary pitcher, and they will also need to fix the bullpen. Let's focus on the pitching aspect of things.
If Breslow wants to build on this team, he'll need to keep Aroldis Chapman as their closer. He's been lights out all season, and they'll need to bring in someone to complement him, especially with Justin Slaten now moving to the 60-day injured list.
As a "buyer", Breslow will have to send over a prospect to promise a team a better tomorrow. Teams like the Royals, Orioles, and Rangers are the top three teams in baseball that have excellent bullpen pieces, including those who eat up the later innings.
Royals' closer Carlos Estevez is under contract until 2027 and is having a career season, leading the league in saves with 22. Orioles closer Felix Bautista, despite some control issues, is still a very threatening pitcher with a 1.8 HR rate and a 2.60 ERA. The last one is Hoby Milner, who's been excellent these past two years and is pitching for Texas. He leads the Rangers' bullpen in strikeouts (37) and has an ERA of 2.01. He's also a lefty submarine pitcher, which puts batters on their toes just from his delivery alone.
But with starting pitching, the best candidates are in the National League. Originally, Sandy Alcantara seemed like a bounceback candidate after returning from Tommy John, but his 2025 has been one of nightmares, including an ERA over 6. However, his teammate Edward Cabrera is an extremely intriguing counterpart. He's posted a 3.78 ERA and is leading the team in strikeouts (and in fact, would be second in that category for Boston, too). He's the perfect candidate for the Red Sox if they want to buy at this year's deadline.
However, these pitchers will be fighting other, and more potent, playoff contenders like the Dodgers, Yankees, Astros, and the Mets. However, the Red Sox have an advantage. Most contenders will be willing to give up prospects, not active players on their roster. The Red Sox have the depth to make it happen, with bats like Romy Gonzalez, Rob Refsnyder, and Abraham Toro, or pitching depth like Richard Fitts, Hunter Dobbins, Lucas Giolito, and Greg Weissert.
Players like Greg Weissert or Lucas Giolito, or even Hunter Dobbins won't get the Red Sox closer to the playoffs; that's already been proven with their 40-43 record. It's time to shake things up. But that's not the "pretty penny"; it's the prospects that'll cost the Red Sox. Prospects like Luis Perales or James Tibbs (from the Devers' trade, #6 team prospect), or Jhostynxon Garcia (also known as "The Password"), and possibly more.
The big "if" is if the Red Sox can improve with these players. Most of these players mentioned are under contract for more than one year (except Hoby Milner, UFA in 2026), and are Breslow-like pieces that he'd want.
Estevez is under contract until 2027, as aforementioned, Felix Bautista will be hitting his second year of arbitration, but is serious trade bait for the last-place Orioles, and Edward Cabrera will be entering arbitration next year as well, albeit in his first year. Most of these pieces the Red Sox can build upon for the next few years if they don't make the playoffs, thus, are "safety" picks in case things don't go as planned.