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Boston Red Sox closer Aroldis Chapman pitching vs the Tampa Bay Rays.

Red Sox Trade Deadline Preview: Likelihood of Each Name Being Traded

The Boston Red Sox have been on a roll recently, riding an 11-game win streak going back to the series against the Los Angeles Angels on Fourth of July weekend. The pitching has been stellar, the offense has turned around, and the team’s looking up as they just got back to a .500 record on Friday night. But the Trade Deadline is quickly approaching. Despite the logical thought process being not to ruin a good thing when it’s going, according to ESPN’s Jeff Passan, General Manager Craig Breslow and the front office aren’t ruling out a fire sale just yet. 

Now, as previously said, it would be quite weird to lean into selling in a down year for the American League, especially when the team is on the brink of making the playoffs right now. They should be doing the opposite. But with the deadline around the corner, let’s look at the trade candidates (based on ESPN’s Top 100 list) and speculate on the likelihood of them being traded. 

Writer’s Note: Two noteworthy pieces of information here.

  • Danny Coulombe (originally 95th) had been DFAd on July 12th and therefore is not eligible on the list now that he’s a free agent.
  • All statistics provided are as of Friday, July 17th. 

Chances of Red Sox Players Being Traded

Aroldis Chapman

ESPN Rank: #10

Stats: 20 Saves, 2.12 ERA, 38/12 K/BB (3.2 Ratio) 

The reigning AL Reliever of the Year is the hottest Red Sox asset on the market right now, and for good reason. If a contender needs a high-end reliever/closer, Chapman is exactly the type of guy needed. While the reliever is in his age-38 season, he is still one of the best closers in the league, in the last year of his contract.

Being the exact type of reliever to push a team into contention, the assumption is the Red Sox would need a lot in return, and it’s uncertain if they would get a lot for a two-month rental. The Red Sox may also believe they are that team and might keep him. It’s uncertain right now.

Trade Probability: 25%

Sonny Gray 

ESPN Rank: #11

Stats: 11-1 Record, 2.54 ERA, 85/24 K/BB (3.5 Ratio) 

The Red Sox found a hidden gem this season when they traded for Sonny Gray. That might be a bit of an obvious point for a former Cy Young candidate, but in his age-36 season, it’s fair to assume that no one expected this type of season out of him. He’s become one of MLB’s premier pitchers this season and one of the most valuable assets on the trade market.

 

There have been talks about trading him just to get something of great value back. He’s in the last year of his contract with team control, with a mutual option for the 2027 season. Ideally, it would be to a contender so it’s beneficial for both sides of the deal, but the Red Sox may have some reservations. Gray’s currently) They’re the only right-handed pitcher in the rotation right now, so removing him from the equation isn’t exactly ideal. Still, the thought process of getting something for him rather than nothing may be intriguing to the front office. 

Trade Probability: 35-40% 

Willson Contreras 

ESPN Rank: #12

Stats: .285 BA/.378 OBP/.547 SLG, 21 HR’s, 62 RBIs

Contreras was also a player coming over from the Cardinals this offseason. Unlike Gray, however, he is under team control for two more seasons after this (2028 team option). He is having a career year this season with the Red Sox, with his 21 home runs being only three shy of his career high in a season, with 66 games remaining. Of course, when they were struggling, Contreras would have certainly been an option on the market, as yet again, a contender needing a bat could’ve used him.

But things are different now. Contreras has been a huge part of the offense’s turnaround during this hot streak. Also, news came out over the All-Star Break that he is unwilling to waive his no-trade clause for at least this season and wants to continue in 2026 with the Red Sox. So that should solve that problem there. 

Trade Probability: 0%

Garrett Whitlock

ESPN Rank: #31

Stats: 4-1 (17 Holds), 2.12 ERA, 38/6 K/BB (6.3 Ratio) 

Another solid reliever for Boston, Whitlock has been a standout bullpen piece on the market despite missing a few games earlier this season. A team needing a set-up man would be great for Whitlock. Ideally, the plan would be to trade him to the opposite league, but for example, a team like the Chicago White Sox could be in the market for him with Seranthony Domínguez and Jordan Hicks slightly struggling.

Boston Red Sox reliever Garrett Whitlock pitching vs Chicago White Sox.
Jul 7, 2026; Chicago, Illinois, USA; Boston Red Sox pitcher Garrett Whitlock (22) pitches against the Chicago White Sox during the eighth inning at Rate Field. Mandatory Credit: Patrick Gorski-Imagn Images

However, Whitlock’s fate on the team is likely entirely dependent on Chapman’s. If he is traded, Whitlock might not be, and vice versa. However, and this can’t be stressed enough, if they are remotely in contention for a playoff spot or higher by the deadline, they should not move them unless the promise of someone who can help this season and the future comes back in return. 

Trade Probability: 15%

Jarren Duran

ESPN Rank: #42

Stats: .193 BA/.256 OBP/.346 SLG, 13 HR’s, 48 RBI’s

The former MVP candidate in the 2024 season has slowly declined and is struggling this year. Of course, the main question is: where does he stand with this team? Sure, former number one prospect Roman Anthony is probably the future in left field. But with no sign of when Anthony will return from injury, it’s unsure of who will take over in left. The bat of Duran could most likely be replaced with Masataka Yoshida, with his bat improving recently. However, when comparing the two defensively, Duran has six DRS compared to Yoshida’s -3 DRS.

Boston Red Sox trade candidate Jarren Duran hitting RBI single vs Tampa Bay Rays.
Jul 17, 2026; Boston, Massachusetts, USA; Boston Red Sox left fielder Jarren Duran (16) hits an RBI single during the sixth inning against the Tampa Bay Rays at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images

Now, when Anthony comes back, Duran should be fair game after the season. But until then, it’s a bit questionable what to do with him. Despite the bad batting average, he is second on the team in terms of RBIs, behind Contreras’s 62. But if they were to trade a position player at the deadline, he seems like the most likely. 

Trade Probability: 65%

Isiah Kiner-Falefa 

ESPN Rank: #63 

Stats: .277 BA/.344 OBP/.361 SLG, two HR’s, 13 RBI’s 

Kiner-Falefa is just one of several utility infielders on the Red Sox roster right now, but he’s a rental with World Series experience. That’s the kind of guy a contender wants in the locker room. It could be understandable, and Boston doesn’t really have a place for him when he comes back from injury, due to the rise of Anthony Seigler, among other infielders. So while it’s unknown if anyone’s deeply interested, he would seem like the easiest asset to move off of. 

Trade Possibility: 50%

Patrick Sandoval

ESPN Rank: #83 

Stats: 0-0 record, 2.08 ERA, five K’s in one start in 2026

Sandoval has been absent with injuries for most of his Red Sox tenure, but is finally back (set to start again on Saturday). He’s more of a depth rotation piece to be perfectly honest, but he has shown through his rehab and his single start this season that he could provide some value to a team, having a short but solid outing against the White Sox. And seeing as the Red Sox have too many left-handers currently, he might be another name that gets flipped pretty easily. 

Trade Probability: 60-65% 

Masataka Yoshida 

ESPN Rank: #98

Stats: .269 BA/.344 OBP/.403 SLG, Four HR’s, 17 RBI’s 

When it comes to the outfielders, as mentioned with Duran, it comes down to these two in terms of who will probably stay. This is another case, like Whitlock and Chapman, where it’s unlikely that they trade both now, especially with Anthony still out.

Boston Red Sox DH Masataka Yoshida hits single vs Tampa Bay Rays.
Jul 17, 2026; Boston, Massachusetts, USA; Boston Red Sox designated hitter Masataka Yoshida (7) hits a single during the sixth inning against the Tampa Bay Rays at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images

But as mentioned, Yoshida’s a better hitter this season while taking the DH role for the time being. In the past, despite being an above-league-average hitter, the Red Sox have deemed his contract hard to move. That might lean them towards keeping him over Duran this season if they have to choose, despite maybe being easier to move than before. 

Trade Probability: 30-35% 

The Last Word 

Trade Deadline season is approaching fast, and it will be interesting to see what the Red Sox do. Again, the reports of selling at the deadline seem far-fetched amid this current winning streak, But these players are all in some trade talks one way or another, so whether or not something happens will be intriguing.

 

Main Photo Credit: Bob DeChiara-Imagn Images

About Will Avila

Will Avila is a writer for Last Word on Baseball, specifically focused on the Boston Red Sox. He previously interned at youbloom, a music company where he wrote sample blurbs for the marketing department to explain about the company. Will graduated from Wheaton College (MA) with a degree in Business and Management. He is currently in the application process for graduate school to get his journalism degree.