When the Boston Red Sox return from the All-Star break on Friday, they’ll be riding a 10-game winning streak with 12 games to go before the trade deadline.
Over the past month, the Red Sox have pulled themselves from a middling team that couldn’t get out of its way to a playoff contender, sitting three games back of first place in the American League East.
Even before the Red Sox took off, chief baseball officer Craig Breslow committed to adding to the team.
“I think we’ve talked a lot about looking to the future, at some point, the future has to be now,” Breslow told The Athletic on June 27. “We went into 2025 expecting to compete for the division and expecting to make it to the playoffs. We haven’t played as well as we’re capable of, but that goal still exists, and we’re not so far away that we should be thinking about 2026 or 2027.”
Since then, the Red Sox (53-45) have gone 13-3 and pushed Breslow firmly into the buyer’s market.
So now a few big questions loom as the second half gets underway:
Can Red Sox avoid a second-half swoon like last two years?
The Red Sox surged into the All-Star break last year, going 9-3 leading up to the break before falling off with a rough road trip after the break. The trade deadline did little to help the team as the additions of starter James Paxton and relievers Lucas Sims and Luis Garcia were quickly injured, and the Red Sox fell out of contention after being 11 games over .500 in early July.
This year’s team is different with the additions of rookies Marcelo Mayer and Roman Anthony, surrounded by a healthy Trevor Story and a veteran Alex Bregman, who is constantly pushing the group forward. At the same time, starter Garrett Crochet has bolstered the rotation.
That’s not always enough, though. The Red Sox have one of the most demanding schedules in baseball after the break and hit the road right out of the gate with six games against the Chicago Cubs and Philadelphia Phillies before returning home for three against the Los Angeles Dodgers.
They’re not going to keep the winning streak going indefinitely, but if they can keep winning series and minimizing errors, they’ll give themselves a chance of sticking around in the playoff hunt.
What kind of pitching will Red Sox get?
We know the Red Sox plan to add, but now it’s a matter of who.
With Hunter Dobbins out for the year and the Red Sox seemingly still uncertain about Tanner Houck’s role, adding a starter has become even more of a priority.
The team would like to add a No. 2 starter to slide between Crochet and Brayan Bello, if they can find one for the right package, an admittedly tricky proposition at the deadline versus over the winter.
Minnesota’s Joe Ryan has been linked to the Red Sox recently, though it’s unclear whether the Twins are willing to trade him. Miami’s Edward Cabrera and Sandy Alcantara could be options. Alcantara, a former Cy Young winner, is coming off Tommy John surgery and had a rough start to the year, a key reason for an ERA north of 7.00, but he has performed better over the past month.
Cabrera is having his best season thus far, but also has a lengthy injury history, and just had an MRI over the weekend for a sore elbow.
Meanwhile, adding to the bullpen is always a priority. While there have been suggestions that the Red Sox could trade closer Aroldis Chapman and get a haul in the process, that would be a significant blow to the club, and if they plan to compete as they’ve said, they’d need to add to replace him. Reliever Jordan Hicks has closing experience, but adding to the bullpen rather than subtracting seems more likely.
St. Louis’ Ryan Helsley has been tied to the Red Sox, but the Cardinals seem hesitant to commit to a buyer or seller strategy. Helsley is a free agent this winter, so he would represent a pure rental reliever. However, he would certainly bolster the bullpen in a setup role.
Will Red Sox trade an outfielder?
The Red Sox already made their most significant trade of the season — and perhaps the biggest trade in baseball this year — sending Rafael Devers to San Francisco on June 15. That undeniably altered the makeup of the team. While it hurt in the immediate term, it didn’t take the Red Sox more than a couple of weeks to find their footing offensively with so many interchangeable players in the lineup.
However, there are almost too many players.
Of course, injuries crop up as the Red Sox have seen all too often this season, but it’s been a daily jigsaw puzzle for Cora to manage playing time, particularly among his outfielders.
Breslow said he doesn’t feel that he needs to trade an outfielder, but managing playing time while keeping players fresh and on time at the plate are all factors the team needs to consider.
At the moment, the outfielder group includes: Jarren Duran, Wilyer Abreu, Ceddanne Rafaela and Roman Anthony as everyday regulars, but Cora also needs to find time for Rob Refsnyder. Meanwhile, the team has said it wants Masataka Yoshida to play the outfield, too, occasionally.
Refsnyder and Yoshida have split playing time at designated hitter. However, there are still four outfielders for three spots, and it’s forced Cora to move his best defensive player, Rafaela, to second base at times to get every bat in the lineup.
The San Diego Padres have expressed immense interest in Duran, though there isn’t a precise fit in terms of trade return with starters Dylan Cease and Michael King about to hit free agency this winter. If the Red Sox do trade Duran, they’d only do so for a controllable starter. General manager A.J. Preller has been creative in the past, though, and could work a trade with another team to then flip that player (likely a pitcher) to the Red Sox for Duran. It seems anything is on the table.
While Anthony is considered all but untouchable, Abreu and Rafaela could be trade pieces, but there hasn’t been as much talk about either of them. Meanwhile, now that Rafaela has found a rhythm at the plate, his eight-year, $50 million deal signed last year looks much better than it did shortly after it was completed and he struggled for consistency.
One other thing to consider is the farm system.
Breslow has shown to be aggressive when trading prospects, as he did in trading the team’s 2023 and 2024 first-rounders, Kyle Teel and Braden Montgomery, in a package for Crochet this past winter. At the deadline last year, he traded infield prospect Nick Yorke for pitcher Quinn Priester, who he then traded this spring for an outfield prospect and a draft pick ahead of the third round this year.
It wouldn’t be surprising, given the outfield crunch at the big-league level, if top outfield prospect Jhostynxon Garcia were part of a trade package. In 40 games at Triple A, Garcia is hitting .292 with a .905 OPS and nine homers. He was Boston’s lone representative at the All-Star Futures Game over the weekend, but there’s not a clear spot for him on the roster.
He could be a key piece in a trade if the Red Sox want to hold onto their proven, young big leaguers.
(Photo of Jarren Duran: Jaiden Tripi / Getty Images)
