It’s Getting Late Early for the Red Sox, Who Must Start the Sell
The 2026 season hasn't gone as planned, and the Red Sox have some valuable trade chips. It's time to cash in and start planning for 2027.
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Following their first postseason berth since 2021, there was a lot of helium surrounding the Boston Red Sox entering the year.
There were definite concerns with their starting lineup, but the pitching on paper should pick up most of the slack. Improved defense, anchored by a corner-infield duo of Caleb Durbin and Willson Contreras, with an outfield trio comprised of any combination of Roman Anthony, Jarren Duran, Ceddanne Rafaela, and Wilyer Abreu.
On paper, this team was built for October when spring training began. Though 66 games in, they look destined for Cancún.
The pitching and defense held up; 11th in team ERA and third in outs above average. The offense, which marred with concerns entering 2026, has been worse than advertised.
Despite Contreras’ best efforts, a career-high 145 wRC+, the Red Sox are the No. 27 offense by that mark. An 89 wRC+ leaves just the New York Mets, Colorado Rockies, and San Diego Padres behind them.
Consequentially, that leaves the Red Sox in an all-too-familiar position: likely seller.
There’s still nearly eight full weeks until the August 3 trade deadline, so there’s hope Boston can turn it around in a weak American League. However, it feels like whenever momentum is building, the group takes several steps back.
Think back to their 2019 title-defense season. Even out of the All-Star break, they were near contention. They even did a soft buy at that year’s deadline. Unfortunately, they missed the postseason by 12 games.
The AL was tougher, especially with fewer teams making the postseason, but 2026 is following a similar pattern; it has cost several longtime employees their jobs, more to potentially follow.
For better or worse, this team seems destined to stay in its own way. Because of this, they have no choice but to start the sell now.
Stats were taken prior to play on June 11.
Start Small, Maybe Season is Salvageable
Reports indicate the Red Sox are already listening to calls on their players. We’ve seen guys significant as relievers Aroldis Chapman, Garrett Whitlock, and Justin Slaten come up. On the position player side, the only name to surface concretely is backup catcher Connor Wong.
Wong, the last man standing from the Mookie Betts trade in 2020, is healthy again in 2026 and his numbers showcase that. Through 82 plate appearances, he’s running a 99 wRC+ with 0.3 fWAR. Those are up from 39 and -0.7, respectively, in 2025.
The Red Sox are looking to trade from their catching depth, something they didn’t have a year ago. With the emergence of Mickey Gasper, hitting .273 with a .321 on-base percentage, there’s less need for Wong. Especially since Gasper has experience with young left-handers Payton Tolle and Connelly Early as it is.
Players like Wong should be the first ones to go in a potential sell for Boston. With Gasper, along with veterans Jason Delay and Matt Thaiss in Triple-A, they have the depth to mitigate the loss. However, Wong shouldn’t be alone in this potential sell.
Veteran utilityman Isiah Kiner-Falefa is another player on the periphery of the roster the Red Sox should look to offload. Already worth the $6 million owed to him this season, his presence likely won’t make or break the Red Sox’s postseason chances. Sure, he’s a respected veteran in a Red Sox clubhouse constantly rife with drama, but he’s redundant on the roster.
Other players on the roster, or on the 40-man, that make sense to move off of sooner rather than later include utilityman Andruw Monasterio, outfielder and designated hitter Masataka Yoshida, and left-handed reliever Danny Coulombe.
Individually, each are important to the team turning it around. However, the Red Sox have in-house options to replace them.
They Have to Address the Outfield
Obviously, if the Red Sox rattle off 10 wins across 12 games, that dramatically changes the temperature on the need to sell. That said, even winning 10 of 12 would still put them several games under .500.
Selling off some pieces of lesser significance is a great place to start, but you can’t win a deadline as a seller unless some big chips don new threads. That’s the likes of the aforementioned relievers, but there are others the Red Sox could — and should — look to recoup assets for.
If there’s no hope in salvaging 2026, there’s really no reason the Red Sox should continue deploying the outfield they have. It’s messy as it is, even with Anthony on the shelf. When he comes back, even if it’s 2027, that problem isn’t going away on its own.
There’s still industry belief that chief baseball officer Craig Breslow holds Duran in higher standing than the rest of the league does. If it’s true, there’s likely no way he’ll find a return that justifies trading the player.
That leaves Rafaela and Abreu. While it’d be rather unthinkable for the Red Sox to move off of younger players with more team control, it’s not out of the realm of possibility. Regardless, that issue needs addressing — and it should’ve been addressed at last year’s deadline.
The Overhauled Pitching Depth
The Red Sox also have two starters who would be sure to garner heavy interest if available. The obvious one is right-hander Sonny Gray. Though his strikeout numbers are down, he’s still posting a 3.20 ERA across his first 11 starts with Boston.
His contract was re-worked in the offseason upon arriving in Boston, with his 2027 now a mutual option. While there’s a chance, especially with the impending lockout, that Gray could accept his end of it, he’s likely going to free agency this winter.
His strikeouts may be down, but he’s generating way more ground balls and, in turn, also keeping the ball in the ballpark better than his final two years in St. Louis.
Less likely to be moved but would garner immense interest is left-hander Ranger Suarez. Suarez signed a lucrative five-year deal with Boston in the offseason, to which he’s excelled. Across 12 starts, he’s posting a 3.18 ERA, a staff-high 1.8 fWAR, and his strikeout rate is up to 24 percent.
He’s one of the game’s best postseason performers ever. That’s not hyperbole, as he’s 16th among 315 pitchers with at least 30 postseason innings with a 1.48 ERA. They signed him to complement fellow lefty Garrett Crochet. Not only has he delivered, but he’s also stepped up in Crochet’s absence since late April.
It’s hard to imagine the Red Sox jump ship in year one of a five-year deal, but this contract is front loaded. Someone like Suarez is immensely talented, but more of a craftsman on the mound. He may age like wine, but there’s definite cause for concern as his velocity dips while he ages.
He’s added nearly a full tick to his average fastball velocity in 2026, but who knows how long that holds up.
Be Open-Minded With Garrett Whitlock
The big-ticket item the Red Sox have this summer is the left-hander Chapman, but the righty Whitlock shouldn’t be too far behind him.
Since the start of last season, Whitlock leads all American League non-closers in reliever fWAR (2.8). Only San Diego’s Adrian Morejon bests him on the National League side. During that span, Whitlock is also 21st in ERA, ninth in FIP, and 19th in strikeout rate.
He’s also sixth in win probability added, trailing Chapman, Mason Miller, Robert Suarez, Cade Smith, and Louis Varland. That’s among 157 qualified relievers since a season ago.
Whitlock turns 30 next week, and he comes with a litany of injury issues historically. He’s a multi-time Tommy John survivor, and had the internal brace procedure done in 2024. He’s also dealt with a hip injury that cost him almost all of the 2022 campaign.
The right-hander has two club options in 2027 and 2028, making him even more attractive on the open market. While it makes sense the Red Sox wouldn’t want to do a full tear down, Whitlock might actually be their most attractive trade chip if he’s on the table.
The One Exception to the Sell
Unless otherwise blown away, the Red Sox should steer clear of trading the first baseman Contreras. Not only is he their best hitter, he’s under team control for two more seasons. Sure, they’re his age-35 and 36 seasons, but he’s fit right in with the ballpark and culture in Boston.
After tailoring his swing to generate more pull air in 2025, he’s leaned into that more this year. His 27.3% pull-air rate is 18th among 169 right-handed hitters entering play Thursday That’s made him especially dangerous at Fenway Park, where he’s hitting .305 with a 151 wRC+ and five home runs.
He’s also taken to first base beautifully on defense. The Red Sox, without a consistent fixture at first base since Mitch Moreland from 2017 to 2020, are benefitting from the continuity. While suitors aplenty will exist for Contreras, the Red Sox should hold him off the market.
That is, unless a team wants to get silly.
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