Let’s not let the last couple of wins fool anyone. As currently constructed, the Red Sox still aren’t good enough to make a serious playoff run.
Yes, they’ve taken the first two games in Seattle and have a chance to complete a sweep before heading to Coors Field to face the Rockies. But two wins don’t erase the bigger issues that have plagued this team for months.
The lineup still lacks the consistent offensive punch needed to compete with legitimate contenders, even in an American League that’s been underwhelming this season. Unless Boston adds one or two impact bats before the trade deadline, it’s hard to envision this club doing much damage in October, even if it sneaks into the postseason.
To be fair, getting there would be an accomplishment in itself. The Red Sox spent much of the season buried in the AL East basement and looked destined to be sellers just a few weeks ago.
Now they have an opportunity to build some momentum against a favorable stretch of the schedule. But until this offense proves it can produce consistently against quality pitching, a healthy dose of skepticism is justified.
If the Red Sox don’t catch fire over the next few weeks and climb back into the Wild Card race, they should be sellers at the deadline. Hanging onto veterans in hopes of backing into the playoffs would be shortsighted.
If they rip off a hot streak and put themselves squarely in the postseason mix, that’s a different conversation.
But if they’re still hovering around .500 or several games out, the smarter long-term play is to move expiring assets, add to the farm system, and avoid chasing a playoff berth that likely ends in another early exit.
The Red Sox have plenty of pieces that would interest contenders if they decide to sell at the trade deadline.
Truthfully, there aren’t many players on the roster I’d label untouchable. Garrett Crochet and Roman Anthony are the two obvious exceptions. Beyond that, I’d at least listen on just about everyone.
One player I’d be very hesitant to move, though, is Willson Contreras.
Boston acquired Contreras from the Cardinals over the winter, and he’s been everything the front office could have hoped for and then some. He’s on pace to set a career high in home runs, has been outstanding defensively at first base, and has emerged as one of the emotional leaders in the clubhouse.
He’s hit a rough patch lately, going just 2-for-18 with nine strikeouts over his last several games, but even with the slump, he’s carrying a stellar .916 OPS as the season nears its midpoint.
Willson Contreras goes deep for a three-run shot!
— MLB (@MLB) April 25, 2026
The @RedSox have scored TEN runs in the ninth 🤯 pic.twitter.com/NiutGcricD
That production, combined with a team-friendly contract, makes him one of the most valuable assets the Red Sox have.
Contreras is under team control through 2027 with a $20 million club option for 2028, and because of that, he’d likely command a significant return on the trade market. The catch, however, is that he owns a no-trade clause and would have to approve any deal.
If Boston trades Contreras, who plays first base? Triston Casas isn’t close to returning, and Romy Gonzalez recently suffered another setback in his rehab. Unless the Red Sox acquire another first baseman as part of a deal, they’d be creating a hole in the lineup while trying to fix other areas of the roster.
Willson Contreras DESTROYS one deep into the night 😮 pic.twitter.com/O4lCPoNWWT
— MLB (@MLB) June 6, 2026
Yes, Contreras is 34 and probably isn’t someone you build the next decade around. But for a team searching for stability and leadership, his value to Boston may outweigh even a sizable prospect package. With a salary cap looming over the game, young players will be more valuable than ever due to their years of control and cheap salaries, which could make teams hesitant to part with prospects.
If the Red Sox can land a young first baseman with upside as part of a larger deal, it’s worth exploring. Otherwise, the smarter move may be to hold onto Contreras and avoid creating a new problem while trying to solve existing ones.
Red Sox Most Valuable Trade Chips
Sonny Gray, RHP
Gray has been everything the Red Sox could have asked for since arriving from St. Louis.
The veteran right-hander has pitched like a legitimate No. 2 starter, going 8-1 with a 3.12 ERA, 55 strikeouts and a 1.18 WHIP across 69 1/3 innings in 13 starts. While his strikeout numbers are down from the 200-plus punchout seasons he posted the previous two years, he’s consistently given Boston quality innings and stabilized the rotation.
If the Red Sox decide to sell, however, Gray could become one of their most valuable trade chips.
The biggest hurdle is his no-trade clause, which carried over from the contract he signed with the Cardinals. But that obstacle may not be insurmountable. If a contender comes calling with a legitimate chance to win a World Series, Gray could be willing to waive it.
Sonny Gray, Devastating Sweepers...and Sword. 🌞⚔️ pic.twitter.com/IEQ8wcYtKp
— Rob Friedman (@PitchingNinja) May 30, 2026
The Braves have already been mentioned as a potential fit, and there are reasons the pairing makes sense. Gray lives in the Nashville area, making Atlanta much closer to home than Boston, and the Braves are always looking to bolster their rotation for a postseason run.
Gray himself recently acknowledged the reality of where the Red Sox stand.
“I can’t speak on behalf of the group, but I can speak on behalf of myself,” he said after last week’s loss to Toronto. “It’s very frustrating. We’re not good. We’re just not a good team right now. That’s just a fact.”
Those comments suggest he understands where the season is headed. If Boston falls further out of contention, it’s not hard to imagine Gray approving a move to a club with legitimate October aspirations.
The Braves and Red Sox have recent trade history, most notably the deal that sent Chris Sale and cash to Atlanta for Vaughn Grissom. A Gray trade would be another significant transaction between the two organizations.
Sonny Gray, Dirty 86mph Sweeper...and Sword. ⚔️ pic.twitter.com/jJcLc3OAwl
— Rob Friedman (@PitchingNinja) May 18, 2026
Even as a rental, Gray wouldn’t come cheap. Boston would owe him roughly $3.6 million over the remainder of the season, plus a $10 million buyout when his 2027 mutual option is almost certainly declined. That’s a sizable financial commitment, but for a proven veteran who has pitched at the top of a rotation all season, contenders may view it as a worthwhile price to pay.
If the Red Sox ultimately become sellers, Gray could be one of the most sought-after starting pitchers on the market.
Aroldis Chapman, LHP
Chapman will be the most coveted relief trade chip at the deadline.
The 38-year-old closer has been dominant, posting a 0.83 ERA and 0.97 WHIP over 21 2/3 innings entering Friday while recording 14 saves and striking out 29 batters against just nine walks.
The Padres have already been linked to Chapman, and pairing him with Mason Miller would give San Diego one of the nastiest late-inning combinations in baseball. The Dodgers also make sense, especially with closer Edwin Díaz sidelined after undergoing elbow surgery to remove loose bodies. Even if Díaz returns after the All-Star break, Los Angeles could look to add another proven high-leverage arm for October.
Aroldis Chapman fires a 102 MPH fastball by Rafael Devers for the strikeout 😤 pic.twitter.com/ryT6WS6OTi
— MLB (@MLB) June 21, 2025
The Brewers are another intriguing possibility. Breslow has a history of making deals with Milwaukee, and if the Red Sox were to send Chapman there, they could target some of the young pitching and position-player talent the Brewers have become known for developing.
While he’s scheduled to become a free agent after the season, he has a vesting option for 2027 worth $13 million if he reaches 40 innings pitched this year. He’s already well over halfway to that mark, and if he’s traded to a contender that uses him regularly, there’s a good chance the option vests.
That means an acquiring team wouldn’t just be getting a rental for the stretch run. It could also gain another season of control over one of baseball’s most effective late-inning relievers, making Chapman an even more valuable asset as the trade deadline approaches.

Paul Rutherford-Imagn Images
May 8, 2026; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Garrett Whitlock (22) delivers a pitch during the eighth inning against the Tampa Bay Rays at Fenway Park.
Garrett Whitlock & Justin Slaten, RHP
Whitlock would be another attractive trade chip for contenders looking for a controllable, high-leverage reliever.
The longest-tenured player on Boston’s active roster has finally put years of injuries behind him and reestablished himself as one of the better late-inning arms in the American League. Better yet for interested clubs, Whitlock comes with two additional years of team control on a reasonable contract, making him more than just a rental.
Because of that, the Red Sox could command a significant return if they made him available.
If Boston trades both Whitlock and Chapman, the back end of the bullpen could quickly become a disaster over the final two months of the season. Even if the Red Sox decide to sell, keeping one proven late-inning arm around for 2027 has value.
If the plan is to move Chapman and promote Whitlock into the closer’s role, another reliever who could draw interest is Slaten.
Justin Slaten, Hammers. ⚒️⚒️ pic.twitter.com/OzfAbczQod
— Rob Friedman (@PitchingNinja) April 17, 2025
Boston acquired Slaten from the Mets in the Rule 5 Draft in December 2023, surrendering minor league left-hander Ryan Ammons and cash considerations. He’s under team control through 2030 and won’t be arbitration eligible until 2027, giving him plenty of value despite a disappointing season.
That said, Slaten’s stock isn’t nearly as high as it was a year ago. The 28-year-old has battled inconsistency and owns a 6.14 ERA, while his injury history adds another layer of risk. Even so, rival clubs may view him as a buy-low candidate with multiple years of affordable control remaining.
For a front office looking to maximize value, Slaten could be the type of arm worth shopping. But if the goal is to land a premium return, Whitlock remains the far more intriguing piece.
Jarren Duran, OF
If the Red Sox decide to sell, Duran should be one of the names they seriously consider moving.
Trading Duran would help clear up Boston’s crowded outfield while allowing the club to capitalize on his value, which remains high thanks to his combination of elite speed, improving power, and defensive versatility. He can handle both left field and center field, making him an attractive target for contenders looking to upgrade multiple areas at once.
With Anthony expected back from the injured list, the Red Sox could comfortably roll out an outfield of Anthony, Ceddanne Rafaela, and Wilyer Abreu. Masataka Yoshida could mix into left field and designated hitter, giving manager Chad Tracy flexibility without creating a logjam.
Jarren has reached base safely in 19 of his last 22 games with this RBI! pic.twitter.com/gMrWR84vMf
— Red Sox (@RedSox) June 9, 2026
The Phillies recently lost Adolis García to season-ending lat surgery and have been patching things together with a platoon of Gabriel Rincones Jr. and Edmundo Sosa in the outfield and should be in the mix. Duran would represent a significant upgrade, bringing athleticism, speed on the bases, and above-average defense to a club with World Series aspirations.
Dave Dombrowski has never been afraid to trade prospects or make aggressive moves to win now, and Duran fits the mold of the type of player who could make an immediate impact.
Have. A. Night. Jarren. pic.twitter.com/KsqguMZ7CE
— Red Sox (@RedSox) May 20, 2026
After taking a step back defensively last season, Duran has rebounded in a big way. He ranks among the league leaders with five Outs Above Average and grades in the 93rd percentile in range in left field, reinforcing his value beyond what he brings at the plate.
The Red Sox would undoubtedly miss his energy and production, but if moving Duran brings back multiple young, controllable pieces that better balance the roster, it’s a conversation worth having.
Wishful Thinking
Trevor Story, SS & Masataka Yoshida, LF/DH
Story’s tenure in Boston has been defined more by injuries than production, and this year’s sports hernia only added to the frustration.
Before landing on the injured list, Story was one of the least productive everyday players in baseball, but it’s fair to wonder how much of that stemmed from trying to play through an injury that eventually became impossible to ignore.
If he returns after the All-Star break and shows signs of life at the plate, the Red Sox should at least explore the trade market. They’d almost certainly have to absorb a significant portion of the roughly $25 million he’s owed next season, but there could be a team willing to take a chance on a healthy Story in a change of scenery.
Story didn’t hide his frustration when the Red Sox fired Alex Cora and five members of the coaching staff earlier this season.
Monster shot for Trevor! pic.twitter.com/kwDcFO6fCt
— Red Sox (@RedSox) May 13, 2026
In the aftermath of the shakeup, the veteran shortstop publicly called for clarity from Breslow and the front office, saying he wanted a better understanding of where the organization was headed.
“Obviously, it’s kinda up in the air what the true direction is,” the shortstop said after Cora was fired. “Those are conversations that need to be had and they’ll be had today and onward going forward, too. I came here to win and I came here to be successful... Some of the direction needs to be cleared up a little bit, in my opinion.”
Marcelo Mayer has settled in as the everyday shortstop and should stay there for the remainder of the season. If the Red Sox aren’t competing, there is little reason to push Mayer aside or shuffle Story around the infield. The organization also has Franklin Arias climbing the system, and creating opportunities for younger players should be part of the long-term plan.
At some point, the Red Sox need to acknowledge that the fit simply hasn’t worked. When Boston signed Yoshida to a five-year, $90 million contract before the 2023 season, the expectation was that he’d become a middle-of-the-order fixture. Instead, injuries and roster construction have reduced him to a part-time designated hitter who struggles to find consistent at-bats.
Masataka Yoshida shows off his arm and cuts down a run at the plate 💪 pic.twitter.com/LgBUuT9lBh
— MLB (@MLB) May 19, 2026
Even with Anthony sidelined, Yoshida has found himself fighting for playing time with role players like Mickey Gasper, underscoring just how crowded and awkward the roster has become.
Yoshida was asked in late May if he asked for a trade and wouldn’t directly answer the question.
“It’s part of the game, right? If it happens, it happens,” Yoshida responded through translator Yutaro Yamaguchi.
A fresh start would benefit both sides and realistically, moving Yoshida would likely amount to a salary dump, and the Red Sox might have to eat money or include a secondary asset to facilitate a deal. But clearing his roster spot would create greater flexibility, open opportunities for younger players, and help reshape a lineup that desperately needs a new look.
Some Value
If Breslow traded Greg Weissert, there’d probably be a segment of the fan base willing to chip in for his Uber ride to Logan Airport.
Weissert has especially struggled when entering with runners on base, routinely failing to strand inherited runners and turning manageable situations into crooked numbers. Despite that, he still has value around the league. He’s under team control for three more seasons and could be an attractive middle-inning option for a contender looking to deepen its bullpen.
At 31, Weissert isn’t likely to bring back a headline prospect, but relievers have a way of commanding surprising returns at the deadline. Just look at the prices teams have paid in recent years. Breslow himself sent four prospects to the Angels for Luis García, proving that bullpen help can become expensive when contenders get desperate.
Greg Weissert, Frisbee Sweeper... 🥏
— Rob Friedman (@PitchingNinja) April 20, 2026
With 24 inches of horizontal break. pic.twitter.com/amRbzAInf7
Veteran left-hander Danny Coulombe is another logical trade candidate.
Outside of a couple of rough outings that inflated his numbers, Coulombe has been dependable for Boston and should draw interest as a pending free agent. Given the organization’s abundance of left-handed relief options, moving the 36-year-old for a prospect or two makes sense, especially if it clears the way for Tyler Samaniego to return to the major league roster.
Zack Kelly could also find himself on the move.
The right-hander was recently optioned in favor of Tyron Guerrero, but he’s continued to produce when given opportunities. Kelly owns a 3.31 ERA in 17 appearances with Boston this season and has been solid at Triple-A Worcester as well. He’s the type of controllable depth arm contenders often target late in July.
As for Guerrero, the Red Sox should absolutely listen.
The hard-throwing right-hander has flashed electric stuff since arriving in Boston, posting a 3.97 ERA with 18 strikeouts and a 1.06 WHIP over 11 1/3 innings. His triple-digit fastball and swing-and-miss ability give him intriguing upside, and it’s easy to envision another organization believing it can unlock even more.
Whether Boston ultimately keeps or moves him, Guerrero’s value may never be higher than it is at this deadline.
