Red Sox For Sale: Boston’s Top 3 Pieces to Move If They Are Sellers at the Trade Deadline

The Major League Baseball calendar has turned to June and as the Boston Red Sox prepare for the summer heat, they may be starting to feel like a crossroad is coming their way in terms of how to approach this year’s trade deadline, which occurs later than usual on August 3. 

On one hand, you have the fact that the American League still stinks, with just five teams over .500 at the time of writing this, one of whom is the Chicago White Sox. After that, the 27-36 Red Sox find themselves just four games back of the final playoff spot, currently held by the sub-.500 Texas Rangers. Boston, of course, would also have to leapfrog the Astros, Twins, Orioles, and Athletics to get there, but the task isn't as surmountable as you may believe. 

On the other hand, though, they have still struggled to gain any momentum in the crowded AL playoff picture thanks to consistent sub-.500 play as a whole, including a league worst 10-21 record at home, and 13-19 record against teams above .500. If this play continues as we inch closer to the trade deadline, and no ground can be gained on any of the aforementioned teams the Red Sox are chasing, it would be a borderline disservice not moving on from the following names.

Ranking Red Sox's 3 Best Trade Pieces

Aroldis Chapman

20 G, 0-1, 0.46 ERA, 19.2 IP, 26/9 K/BB, 1.99 FIP, .134 AVG, 13 Saves, 0.8 fWAR 

Maybe the most obvious name on the list of players the Red Sox should be looking to deal if they are sellers is their All-Star closer Aroldis Chapman. Chapman is currently on a one-year, $13.3 million contract with a conditional mutual option for 2027, which becomes guaranteed with 40 IP in 2026 plus a passed end-of-year physical. The deal also comes with a $300,000 buyout, and he has already begun garnering interest as USA Today Sports’ Bob Nightengale reported last month that the “San Diego Padres are eyeing the veteran reliever on the trade market.”  

While it would without a doubt be tough to see Chapman go and probably signal the waving of the white flag on 2026, his dominant performance and expiring contract makes him a chip the Red Sox must cash in on if they find themselves out of the playoff race come August. Chapman himself is no stranger to a deadline move, as fans will recall he was dealt at the 2016 trade deadline from the Yankees to the Cubs in exchange for RHP Adam Warren, outfielders Billy McKinney (ranked No. 5, in the Cubs system), and Rashad Crawford, and a 19-year-old shortstop by the name of Gleyber Torres who was not only Chicago’s top prospect, but the No. 24 prospect in all of baseball. 

Now, even though the Yankees were shipping out a 28-year-old version at the time as opposed to the 38-year-old one that the Red Sox would be moving on from, his production this season isn’t all that far off from where it was back then as Chapman finished 2016 with a K% of 40.5%, a whiff% of 36.8%, and a chase% of 32.5%. Fast-forward 10 years and outside of an understandable drop in average fastball velocity from 101.1 to 97.4 mph, his K% (34.7%), whiff% (33.3%) and chase% (32.2%) all still register as great to elite. If the Red Sox are serious about moving Chapman, then the asking price, even with his age and contract situation, should still be high. If the Padres are the team to come calling for instance, then one of their top two prospects -- catcher Ethan Salas (No. 51 in MLB) or left-handed pitcher Kruz Schoolcraft (No. 90) -- would be a great prize,

As for a potential framework to go off of from last year’s deadline, while more upper-echelon arms closer to Chapman’s stature like Jhoan Duran and Mason Miller were moved, the deal to look at that fits a similar situation, i.e. a big arm on an expiring deal, is the Ryan Helsley trade. The Mets acquired Helsley, who had a 3.00 ERA and 41 strikeouts over 36 innings from the Cardinals for two top-20 prospects according to MLB Pipeline in infielder Jesus Baez (No. 8) and right-handed pitcher Nate Dohm (No. 14), as well as right-hander Frank Elissalt. 

If he does in fact become available, teams will be lining up for Chapman’s services and the Red Sox would be foolish to come away with anything other than a king’s ransom if a bidding war breaks out.

Sonny Gray

11 G, 7-1, 3.20 ERA, 56.1 IP, 44/16 K/BB, 3.94 FIP, .252 AVG, 0.8 fWAR  

The second of Boston’s expiring contracts that makes the most sense to move on from is veteran starter Sonny Gray. Much like Chapman, there is a mutual option for 2027 with a luxury tax cap hit of $25 million and buyout of $10 million that gets forfeited if the Red Sox exercise the option but Gray opts out. While he hasn’t been the strikeout pitcher he was advertised to be when the Sox acquired him from St. Louis this offseason, seeing his K% drop from 26.7% to 19.9%, he’s seemingly reinvented himself as a pitch-to-contact pitcher who’s excelled at avoiding hard contact with a Hard-Hit% of 33.8%, good for the 76th percentile and a far cry from his 40.7% and 48th percentile finish in 2025. 

Also similarly to Chapman, Gray is no stranger to being dealt at the trade deadline. Back in 2017, a 27-year-old Gray was traded from the Athletics to the Yankees for outfielder Dustin Fowler (No. 4 in the Yankees system), infielder Jorge Mateo (No. 8) and right-hander James Kaprielian (No. 12), none of whom were considered Top-100 prospects in MLB Pipeline’s eyes, but were each able to put together seasons in the big leagues throughout their careers, with Mateo seeing the most success and longevity. 

When it comes to moving Gray and what to realistically expect to get back, the Red Sox can use their own framework from what they gave up to get him: Young, controllable arms with big league experience like Richard Fitts, and those with upside potential like Brandon Clarke (No. 5 in the system). They could also look to a deal from last year’s deadline, when the Rangers acquired fellow veteran right-hander on an expiring contract, Merrill Kelly, from the Diamondbacks. Kelly, who owned a 3.22 ERA over 22 starts at the time, was sent south for left-handed pitchers Kohl Drake (No. 5 in the Rangers system), and Mitch Bratt (No. 9), along with right-handed pitcher David Hagaman (No. 13).

If a team comes calling offering up three top-20 prospects for the services of Sonny Gray, or a similar package that includes a young player who can help the Red Sox now, Craig Breslow should jump at the opportunity to collect on a veteran arm with no long-term future in Boston.

Isiah Kiner-Falefa   

31 G, .267/.327/.333, 85 wRC+, 4 SB, +5 OAA, 0.7 fWAR

This final trade piece may come as a surprise to those looking to see Jarren Duran or Willson Contreras on this list. While those deals would make sense -- a Duran trade would finally put an end to the outfield logjam if and when Roman Anthony returns, and you could possibly get a haul the way Contreras is producing -- don't expect the front office to blow up the foundation they built over the last few years just because of one bad half of baseball.

Enter an alternative option on another expiring contract who has had trade deadline experience before: Isiah Kiner-Falefa. Such a trade may have seemed like a laughable proposal coming out of a March/April run that saw him hit just .229 with an OPS+ of 44 and wRC+ of 38, but the man who said he was fighting for his career found a way to drastically turn things around in May, slashing .385/.467/.513/.979 with one home run and eight RBIs. He forced his way into a lineup starving for production and may get some looks from contenders after all. 

When Kiner-Falefa was brought in on his one-year, $6 million deal by the Red Sox, the belief was he’d be a solid utility infield option that also possessed a strong veteran leadership presence and postseason experience fresh off a trip to the World Series with the Toronto Blue Jays. Look around the current playoff landscape as of today and you’ll see plenty of young or inexperienced teams such as the Cardinals (26.7 years old on average), White Sox (27.4), Pirates (27.5), and Athletics (27.5), all in the top 10 of the youngest teams in the league, volleying for playoff positioning and potentially looking for a veteran who knows what it takes to win in the postseason. Factor in some of the more experienced squads like the Dodgers, Braves, and Padres who may just look to fill out their rosters with an additional piece, and Kiner-Falefa could be a name that surprisingly works for a lot of teams. 

In terms of what he could bring the Red Sox back in return, the Blue Jays and Pirates may have painted the picture back in 2024, when he was dealt from Toronto to Pittsburgh for minor-league utility man Charles McAdoo, who since the deal has turned into a top-30 prospect with the Jays (No. 25).

If Boston truly does fall out of contention as we approach the August 3 trade deadline, it is imperative they identify which players they see as long-term pieces that can help the club’s future and which ones, especially these three listed, they should move on from in order to set themselves up for the most success moving forward.