Get ready, as Boston is cooking up a major shake-up. And yes, their latest offseason move isn’t just about Alex Bregman, but a five-player blockbuster trade. Remember when the Red Sox picked up Sonny Gray from the Cardinals a few days back and hinted they might not be done upgrading the rotation? Turns out they meant it.

Now, the Red Sox have pulled the trigger on another big deal that not only shakes up their current roster but could also set the stage for bigger decisions ahead, including what happens with Bregman and Pete Alonso.

“Trade news: The Boston Red Sox are acquiring right-hander Johan Oviedo in a deal that will send outfielder Jhostynxon Garcia back to Pittsburgh, sources tell ESPN. In total, it’s a five-player trade,” ESPN’s Jeff Passan reported on X. But it doesn’t end there.

Heading to Pittsburgh are top outfield prospect Jhostynxon Garcia and pitcher Jesus Travieso, while Boston also picks up pitching prospect Tyler Samaniego and catching prospect Adonys Guzman.

But if you think the names sound good, wait because the move is raising some eyebrows in Boston. It is because of Oviedo’s injury history. Reportedly, elbow soreness led him to Tommy John surgery in late 2023. That wiped out his 2024 season, and then a lat strain delayed his 2025 return. He didn’t get back on a mound until August this year, when he made nine appearances and posted a 3.57 ERA.

Still, Oviedo could be a setup guy for Gray! But now comes the bigger twist.

The Cubs are circling back on Alex Bregman. As you may recall, they attempted to sign him last spring to a four-year, $115 million deal with opt-outs. But he chose Boston. Now, with Chicago unlikely to re-sign Kyle Tucker and Bregman heading into free agency, the fit might finally be there.

And as for the Red Sox, they seem to be shifting their attention toward Pete Alonso as a major target heading into the Winter Meetings. However, now the question is, while Alonso’s track record with the Mets speaks for itself, could he slide in as a natural replacement if Bregman ends up elsewhere?

The Red Sox are looking for a Bregman replacement

Even though the Red Sox are still expected to go after Alex Bregman, they’re not putting all their eggs in one basket. Chief Baseball Officer for the team, Craig Breslow, is reportedly eyeing other big names like Pete Alonso. Alonso hit 38 HRs this year, which almost felt underwhelming for him, considering he has already had three seasons with 40-plus bombs in his seven-year career. But guess what, Alonso still has gas left in his tank.

Meanwhile, Boston’s home run leader was Trevor Story with just 25. And in case you missed it, Rafael Devers is now with the Giants. So, bringing in a power hitter like Alonso would definitely juice up the Red Sox lineup. But replacing what Bregman offers defensively and as a leader wouldn’t be easy.

That said, the Red Sox are in a strong position to land Alonso, especially since his free-agent market seems to be moving pretty slowly. Not many teams are ready to hand him a seven-year deal worth over $200 million. However, Boston actually has the room to make such an offer.

He will soon turn 31. The right-handed hitter can offer balance to a lefty-leaning lineup. Plus, he will have a strong veteran voice on a younger team. And considering he played his entire career for the Mets, he understands the pressures of playing for a big market. It will be interesting to see where this goes.

As a right-handed-hitting first baseman, he would give the Sox options. The team can have first baseman Triston Casas begin the year at Triple A to build up reps after missing almost all of 2025 due to a ruptured left patellar tendon. Otherwise, they could have Casas and Alonso at first, easing Casas back into action.