Cubs eye – With the Red Sox still far from postseason contention, Sonny Gray could resurface on the trade market. A deal with the Chicago Cubs would send Gray to Chicago while Boston weighs moving Matt Shaw, whose early MLB numbers remain promising despite a back tightne
On a day when the Red Sox are still uncomfortably distant from postseason contention, the name Sonny Gray keeps showing up as a lever Boston could pull. The problem is simple: if Boston’s season is slipping away, then a prized offseason addition can start looking like a tradable asset.
Gray’s situation is already laid out in dollars and innings. Boston is paying $11 million of his $31 million contract for this season. and the deal runs with a mutual option—plus a $10 million buyout—for 2027. Even at 36 years old, Gray hasn’t looked like a throwback. Across nine starts and 44 innings, he has posted a 3.27 ERA and a 1.21 WHIP with 34 strikeouts.
For the Cubs, the pitch isn’t abstract. Their rotation has been injury-ravaged, and the idea of adding Gray’s innings—right now—goes straight to the day-to-day problem of trying to stop the bleeding before the season slips too far.
That’s where this potential swap gains its sharpest edge: Boston could use Gray’s remaining trade value to address needs on the infield side, while Chicago gets immediate, proven pitching depth.
The heart of the deal. in that version of reality. is swapping Gray for Matt Shaw—an outcome that carries a bit of baseball irony. The piece of it that makes fans lean in is the circular nature of the comparison: replacing Alex Bregman with the guy Alex Bregman replaced on the Cubs. But there’s more than a cute storyline here; Shaw’s profile matters.
Shaw is currently on the IL with back tightness, but the situation doesn’t seem too serious. Boston would be taking a swing at development as much as production. Shaw is only 24, and the Red Sox would be betting that he can keep moving quickly from flash to reliability.
In his first year-plus, Shaw’s numbers have been good enough to keep the discussion grounded. He has a .691 OPS and 100 OPS+ (95 wRC+) through 104 plate appearances, which lands him around league-average offensive production in this snapshot. He struggled early as a rookie. then closed strong: he posted a .766 OPS with seven home runs over the final two months of the regular season.
Defensively and physically, Shaw’s tools are part of the argument. He has baseline speed and defensive versatility that could let Boston deploy him at second or third depending on needs. He’s in the 93rd percentile for sprint speed. There’s also evidence that his approach at the plate has improved. with his strikeout rate at 17.3 percent compared to 21.5 percent during his rookie season.
Power still isn’t the most consistent part of the package. The more grounded need for him is to work for more walks. Even so, the case here is contact and coverage—he can generate healthy contact, spray hits all over the field, and he brings real speed into games.
In the framing of a Gray-for-Shaw swap. the “why would Boston do it” answer leans on one idea: if Shaw’s value is rising. and Gray’s contract and current performance keep trade doors open. Boston has a real incentive to move. The counterweight is the timing—Boston would have to follow through on Shaw’s development, not just acquire him.
The Red Sox would also have to decide how much they need to add to make the trade work for Chicago. The framework suggested is that Boston might need to give up a prospect in addition to Sonny Gray—something the Cubs would have interest in. The hope for both sides is that the exchange gives each team what it’s actually looking for: Gray as immediate pitching help for Chicago. and Shaw as a longer runway piece in Boston’s infield.
For Chicago, the “why would the Cubs do it” argument is tied to the calendar. The Cubs are sliding, but they still have a talented roster and a real chance to push deep into October. The hinge is staying healthy enough—especially in the rotation.
If the Cubs can get even semi-healthy, the thinking goes, they stabilize quickly. Gray fits that exact need because he’s been built to eat innings: he has pitched 165-plus innings in three straight seasons.
The roster around him matters too. Justin Steele will return eventually, and Matthew Boyd isn’t down for the count. Ben Brown has fully broken out, and Shōta Imanaga still looks like an ace—these last couple weeks notwithstanding.
In this version of the deal, Gray doesn’t just smooth out a rough patch. He transforms the Cubs’ immediate rotation into something more respectable, and it sets them up for what could become near-unmatched depth once the playoffs arrive.
But then comes the difficult truth embedded in the trade logic: if Chicago is considering moving Shaw, Shaw is already living in the reality of MLB rosters—where “expendable” is often just another word for “not in the starting lineup long enough to make the team regret it.”
The piece of Chicago’s internal decision-making is blunt. Shaw’s path was effectively iced out after the Cubs handed long-term contracts to Alex Bregman and Nico Hoerner. With Shaw on the IL, Chicago’s second-ranked current prospect, Pedro Ramírez, is getting his shot. Ramírez was one of the hottest bats in the minors prior to his call-up. Kevin Alcántara also received a call-up recently.
That’s the roster math behind calling Shaw expendable—talented, capable of big things, but not necessarily guaranteed to reach whatever peak he might be able to reach as a Cub.
The trade idea lands differently depending on which jersey you’re imagining. For Chicago, it’s a calculated bet to stop the rotation from breaking the season apart. For Boston, it’s a move that keeps a young, developing bat in play while turning the right starter into infield flexibility.
Either way, the stakes are immediate: a Boston team that still isn’t close to the postseason can’t afford to let its best trade options sit untouched. And a Cubs team fighting through injuries can’t afford to wait around for the rotation to magically fix itself.
Sonny Gray Matt Shaw Chicago Cubs Boston Red Sox MLB trade postseason contention injured list rotation depth