​Over the next few weeks we’ll be doing some theorizing about optimal returns at the trade deadline as the Red Sox contemplate another teardown in the middle of a season that looked doomed, and then—perhaps—didn’t. The mood has shifted, though: what began as a potential hopeless slog might now be a path to something more promising. Boston, after sweeping the Yankees, then dropping two of three at home to the Nationals (hardly a highlight reel moment), bounced right back with another sweep—this time against the Angels and the White Sox. And now the Mets are in the mix. Nine straight wins after yesterday afternoon’s Queens romp, 17-6 in their last 23 games, and 14-2 in their last 16. The standings have begun to look almost unfathomable, and the arc of the 2026 Red Sox has altered in ways that would have startled anyone three weeks ago. Craig Breslow now faces a decision he probably didn’t expect to be weighing so soon: should he stay the course with selling, or pivot toward a buying posture?
Aroldis Chapman had been pegged as the headline act of the sale. Sonny Gray was widely viewed as the prize the contenders would chase. Willson Contreras also figured into conversations if this were a true teardown. If Breslow begins to tilt toward buyer mode—even if only marginally—all three of those conversations flip. You don’t trade your best pitcher, your most consistent arm in the rotation, or your powerful first baseman when you’re trying to win. You retain them and build around them.
So what does Boston need? First, a healthy middle infielder who can stay on the field—this roster cannot absorb another injury at a key position. Second, another arm to soak up innings behind a rotation that’s still coping with the absence of Connelly Early and Garrett Crochet, with Patrick Sandoval just making his debut in the series finale in Chicago. And third, bullpen reinforcement for when games actually matter. None of this is impossible, and all of it comes with a cost.
Houston has spent most of this decade being insufferably great—in the best possible way—winning the division, the World Series, and basically everything else. So it’s genuinely satisfying to see them look a little uncertain in 2026. Is this schadenfreude? It might be. They’ve had three managers since the cheating scandal broke: AJ Hinch was fired within two months of the scandal surfacing, just before the 2020 season got underway; Dusty Baker arrived and briefly reestablished them as champions before stepping away after 2023. Now Joe Espada is trying to keep the lights on with what remains. The core of that juggernaut has aged out or moved on—Jose Altuve experimenting with and failing in left field, George Springer landing in Toronto, Alex Bregman becoming a Cub (a small grumble from this corner), which means July gets interesting for a team with unclear direction. OK, Carlos Correa still has a +121 OPS coming back to Houston from Minnesota, whatever that means in the grand scheme.
Jeremy Peña is the shortstop Jeff Passan links to Boston in his deadline top 100, though not as a headliner—he appears as a name in the mix, not the centerpiece of a rumor. It’s worth noting before getting too excited: Peña has spent time in the spotlight for SEO purposes. In other words, keep expectations measured as you scan the rumor mill. This is a season in which the scope of what’s possible can shift quickly, and the Red Sox’ strategy could hinge on the smallest of details as the calendar turns toward July.