The Boston Red Sox remain uncomfortably far from postseason contention, which could put prized offseason addition Sonny Gray right back on the trade market. Boston is paying $11 million of Gray’s $31 million contract for this season, with a mutual option (and $10 million buyout) for 2027.
Gray still has solid stuff, even at 36 years old. The three-time All-Star has a 3.27 ERA and 1.21 WHIP across nine starts and 44 innings, with 34 strikeouts. If there’s one contender desperate enough to roll the dice on Gray right now, it’s probably the Chicago Cubs with their injury-ravaged rotation.
This Red Sox-Cubs trade could help all sides
This is clean and simple. Chicago adds the quality pitching depth it so plainly needs, while Boston addresses a long-overdue concern in the infield. Replacing Alex Bregman with the guy Alex Bregman replaced on the Cubs is a fun ironic twist, if nothing else. But Shaw has the talent to develop quickly into a productive, everyday bat for the Sox.
Perhaps the Red Sox would have to give up a prospect in addition to Sonny Gray that the Cubs would have interest in (and maybe could also help them in the 2026 season as well), but the framework for Gray and Shaw swapping could serve the purpose of both sides.
Why the Red Sox say yes
Shaw is currently on the IL with back tightness, but it does not seem too serious. In reality, turning 36-year-old Sonny Gray — midway through a lost season — into a 24-year-old former top prospect is a total heist job. Boston would need to follow through on Shaw’s development, of course, but Shaw has flashed major talent over his first year and change in the majors.
He has a .691 OPS and 100 OPS+ (95 wRC+) so far in his sophomore season, which essentially puts him around the league average for offensive production through 104 plate appearances. As a rookie, he struggled out of the gate but posted a .766 OPS with seven home runs over the final two months of the regular season.
Shaw has baseline speed and defensive versatility to support his value; Boston can roll him out at second or third, depending on needs. He’s in the 93rd percentile for sprint speed. There is also tangible evidence of an improved plate approach, with Shaw’s strikeout rate noticeably down (17.3 percent) compared to his rookie numbers (21.5 percent).
He has not generated much consistent power yet, and Shaw needs to work more walks, but he can generate healthy contact, spray hits all over the field, and burn rubber. There’s something here for Boston.
Why the Cubs say yes
While this move seems shortsighted — it is, to be frank — sometimes you need to push your chips in. Chicago has been on a troubling slide these past couple weeks, but this is a very talented roster with a real chance to push deep into October. If the rotation can get even semi-healthy, the Cubs will stabilize quite a bit. Gray has pitched 165-plus innings in three straight seasons.
Justin Steele will return eventually. Matthew Boyd isn’t down for the count. Meanwhile, Ben Brown has fully broken out and Shōta Imanaga still looks like an ace (these last couple weeks notwithstanding). Gray transforms the Cubs’ immediate rotation into a more respectable unit, but really sets them up for near-unmatched depth once the playoffs arrive.
As for trading Shaw, that’s just life in the majors. Not every prospect gets to break out with their original team — even the best prospects. The Cubs handed long-term contracts to Alex Bregman and Nico Hoerner, effectively icing Shaw out of the everyday lineup. Now, with Shaw on the IL, Chicago’s second-ranked current prospect, Pedro Ramírez, is getting his shot. He was one of the hottest bats in the minors prior to his call-up.
Kevin Alcántara also received a call-up recently. The Cubs aren’t running out of young, explosive hitting talent any time soon. That means, quite frankly, that Shaw is expendable. Talented, no doubt. Capable of big things. But he’s not necessarily destined to achieve whatever he achieves at his peak as a member of the Cubs. That’s okay, especially if you’re a Red Sox fan.
More MLB news and analysis:
Add us as a preferred source on GoogleFollow
