No, you weren't dreaming. The Boston Red Sox really did trade star slugger Rafael Devers to the San Francisco Giants on Sunday evening, hours after polishing off a sweep of the New York Yankees that had just vaulted the team back into the race for the AL East.
It had been a bumpy ride for Devers and the Red Sox over the last few months, from his handling of Alex Bregman's arrival to all the drama surrounding his unwillingness to pick up a glove again after being told he'd be a full-time DH (and his penchant for taking his criticisms of his front office to the media). But through it all, Devers had continued to hit like usual — his last home run in a Boston uniform came on Sunday off New York ace Max Fried — and no matter how uncomfortable things got at times, no one expected him to be sent packing like this.
Well, maybe no one except for Red Sox fans. The past two decades have brought plenty of highs for Boston baseball, including a whopping four World Series titles. But for a team that's seen so much success, they've also seen a whole lot of painful divorces with players they thought were or would be the face of their franchise. Devers has now been added to that list, but is this the most heartbreaking deal in recent Red Sox history? Let's break it down.
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5. Jon Lester and Jonny Gomes for Yoenis Cespedes and a draft pick (2014)
Eight losses in nine games leading up to the 2014 trade deadline convinced Ben Cherington and the Red Sox that it was time to sell. And with Lester months away from free agency and having already turned down an extension offer, he was Boston's biggest asset.
Rather than look for a haul of prospects, though, Cherington wanted a quicker fix, unwilling to fully lean into a rebuild just a year after winning the 2013 World Series. So he flipped Lester to Oakland for Cespedes, a tantalizing slugger who appeared to be a perfect fit for Fenway Park.
It didn't quite work out that way. Cespedes largely struggled down the stretch, and Cherington flipped him to the Detroit Tigers that winter. Lester only spent a couple of months with the A's, who lost a thrilling Wild Card game to the Kansas City Royals that October. But he went on to sign a massive deal with the Chicago Cubs that winter, leading them to a World Series title in 2016.
4. Chris Sale for Vaughn Grissom (2023)
Just about everybody in Boston felt like it was time to move on from Sale; injuries had put his five-year, $145 million contract under water, and his days as a perennial Cy Young candidate seemed to be behind him. But even if you thought Sale was damaged goods, flipping him to the Atlanta Braves for Grissom — a middle-infield prospect who might not be able to stick in the middle infield and who already had serious questions about his bat — felt like a puzzling decision from new chief baseball officer Craig Breslow.
Of course, the fact that Sale immediately put together a healthy, Cy Young-winning season in Atlanta in 2024 (and has been nearly as good so far this season) just rubbed salt in the wound. Grissom, meanwhile, appears to be leveling out as a Quad-A player; he posted a .465 OPS in 31 games with the Red Sox last year, and is currently slugging .378 in Triple-A.
3. Jeff Bagwell for Larry Andersen (1990)
We have to go back a little ways for this one, but we promise it's worth it; just ask any Red Sox fan who's old enough to remember it.
A Connecticut native, Bagwell started mashing in the Minor Leagues immediately upon being drafted by the Red Sox in the fourth round in 1989, working his way onto top-100 lists in the process. But just a few months later, Boston found themselves in a dogfight with the Toronto Blue Jays in the AL East, so they flipped Bagwell for some relief help in Andersen.
For a while, it seemed like a wise move: Andersen pitched to a 1.23 ERA in 15 appearances down the stretch with Boston, helping the team capture a division title by two games. But the Red Sox would be swept out of the ALCS that year ... while Bagwell won Rookie of the Year honors with the Houston Astros in 1991 and never looked back en route to a Hall of Fame career. Ouch.
2. Rafael Devers for Jordan Hicks, Kyle Harrison, James Tibbs and Jose Bello (2025)
Look, I get the concerns. Devers did not cover himself in glory with the way he handled his move from third base to DH (and his attempted move from DH to first base in the wake of Triston Casas' injury). And it's fair to wonder how his 10-year mega-deal will age.
But he's still just 28 years old, and he's still one of the 15-20 best hitters in baseball. Letting a player like that go, smack in his prime and fresh off a stirring sweep of the division-leading New York Yankees, has to sting — especially when you consider the relatively underwhelming return Breslow got after reportedly not even bothering to shop Devers around.
Maybe the clubhouse situation around Devers had grown untenable, and Boston had to make a move now. That doesn't make it hurt any less: If anything, it should have fans raising an eyebrow at how the last few months have played out, beginning with the decision to sign Alex Bregman seemingly without doing any legwork to get Devers on board. Maybe Harrison finally puts it all together, Hicks breathes fire out of the bullpen and Raffy's bat diminishes in a more pitcher-friendly park. But it's tough to stomach shipping out your best hitter in the middle of a playoff push for seemingly nothing other than financial flexibility and some massaged egos.
And yet, there's still no argument for it to claim the top spot on this list.
1. Mookie Betts and David Price for Jeter Downs, Alex Verdugo and Connor Wong (2020)
Even if you think Boston lost the Devers trade, you can at least come up with reasons why the team might have been skeptical about investing in him long-term. None of those arguments existed with Betts, an MVP-caliber player and consummate teammate who had just helped lead the Red Sox to a World Series title in 2018.
In return, all Betts wanted was for Bloom and owner John Henry to pay him what he was worth. But, for some inexplicable reason, that proved too much to ask, and so the Red Sox forced themselves to send him to the Los Angeles Dodgers for pennies on the dollar. And that isn't hindsight talking: Downs was a solid prospect, and Verdugo had established himself as a perfectly solid starter in the Majors, but neither looked anything like a star even at the time.
Betts, by all accounts, wanted to spend the rest of his career in Boston, and he'd done absolutely nothing to discourage the Red Sox from making that a reality. There were no questions about his leadership ability, no roster crunch that needed to be resolved. It was just about the money, and for that, Bloom and Henry should never be able to live it down.