It wasn’t just that the Red Sox traded Rafael Devers. It was how they did it. Father’s Day at Fenway, Yankees in town, and minutes before first pitch, the news dropped—Boston had dealt the last of their homegrown cornerstones to the San Francisco Giants. A total bombshell out of nowhere.

Devers was a three-time All-Star, a two-time Silver Slugger, and just 29 months into a $313 million extension that was supposed to make him the face of the franchise for the next decade. And just like that, he was gone.

Betts. Bogaerts. And now Devers. Three cornerstone players — all drafted, developed, and beloved in Boston — are now starring somewhere else. One by one, the Red Sox have let go of the kind of talent most franchises build around. And at some point, it stops feeling like bad luck and starts looking like a blueprint.

So here we are again, asking the same exhausting question: How did this franchise, once defined by loyalty and legends, let it happen a third time?

The Devers Deal in a Nutshell

Boston sent Rafael Devers — and the $250+ million left on his contract — to the Giants. In return, they got lefty starter Kyle Harrison, flamethrower Jordan Hicks, outfield prospect James Tibbs III, and 20-year-old reliever Jose Bello. It’s a mix of now and later, headlined by Harrison, who immediately steps into a big-league rotation that desperately needs upside.

But what makes this trade sting isn’t just the player swap. It’s the moment. This wasn’t a quiet deadline-day move. It dropped on Father’s Day, right before first pitch against the Yankees.

And then came the quotes. Chief Baseball Officer Craig Breslow insisted the move wasn’t a white flag, saying “this is in no way signifying a waving of the white flag on 2025,” and that they “couldn't find alignment.” For fans still reeling from the departures of Betts and Bogaerts, it felt like more front-office speak — more buzzwords in place of accountability.

Deja Vu All Over Again: Betts, Bogaerts, Devers

Red Sox fans have lived this movie twice already — and never got the happy ending.

The Betts Blunder (2020)

Let’s go all the way back to February 2020, when the Red Sox traded away Mookie Betts, arguably the most complete player to come through Boston since Pedro or Papi. He was 27 years old, an MVP, four-time Gold Glover, four-time All-Star, and a fan favorite who did everything right. And they moved him anyway.

The justification was that the team wanted to reset the luxury tax and get something in return before he hit free agency. But the return package — Alex Verdugo, Connor Wong, and Jeter Downs — was never going to match Betts’ impact. Meanwhile, Betts signed a 12-year, $365 million extension with the Dodgers before he ever played a game for them, won a World Series his first season, and added a second ring in 2024.

That trade became a permanent scar on the front office’s reputation, and everything that’s happened since has been viewed through its lens.

The Bogaerts Breakdown (2022)

Two years after trading Mookie Betts, the Red Sox were adamant that they wouldn't make the same mistake with Xander Bogaerts. Publicly, they said all the right things — how much they valued him and how he was the heartbeat of the clubhouse. Privately, though, the offer they put on the table told a different story.

At the start of the 2022–23 offseason, Boston floated a six-year, $160 million deal. That might’ve worked in a different era, but it barely got them in the room in a market where shortstops were landing deals well north of $250 million. Trea Turner signed for $300 million. Carlos Correa had multiple $300M offers before medical flags. Bogaerts, coming off arguably his best season — .307 average, 5.7 WAR, and Gold Glove-caliber defense — was more than justified in expecting something competitive.

So he opted out, and San Diego came through with an 11-year, $280 million deal that blew Boston’s out of the water. Bogaerts took it.

Chaim Bloom later admitted he had regrets. Fans didn’t need to hear that. They’d already drawn their own conclusions: this front office doesn’t close. From Mookie to Xander, the pattern was becoming painfully familiar — wait too long, underbid, then spin the fallout.

Devers: The Last Man Off the Island

With Betts and Bogaerts gone, the Red Sox were running out of excuses — and out of stars. So when they signed Rafael Devers to a 10-year, $313.5 million extension in January 2023, it felt like a course correction. Finally, a commitment. Finally, a homegrown star staying put.

The truth is, the Devers deal was less of a proactive strategy and more of a reaction to the PR backlash that followed Bogaerts walking to San Diego. And Devers — young, productive, and already part of the family — became the answer.

Eventually, things just came to a head. The tension that had been simmering since the spring finally boiled over. Positional disputes, changing expectations, and the sense that Devers was being moved around to patch holes he never created — it all piled up.

Where Does Boston Go From Here?

The East Isn’t Waiting

There’s no easing into a rebuild in the AL East. The Rays keep unearthing relievers no one’s ever heard of and turning them into back-end monsters. The Yankees still print money and toss nine-figure contracts around like candy every winter. And the Orioles? They’re stacked with young talent and playing like they know it’s their time.

For the Red Sox, there's no soft landing here. If they want to compete in this neighborhood, they need stars. Kyle Harrison needs to develop into more than just a mid-rotation arm. Jordan Hicks has to provide stability in a bullpen that’s been held together with duct tape. And at least one of the young bats — James Tibbs III, Roman Anthony, whoever — has to break out.

Youth Movement or Half‑Measure?

The Red Sox have talent in the pipeline, but anyone who’s followed this team knows that banking solely on young guys with no vet support is asking for growing pains, especially in Boston.

Fenway’s not a gentle learning environment. One bad start turns into two weeks of noise. One fielding error can follow a kid into the clubhouse. If this youth movement is real, the team’s going to have to build a support system around it.

Fan Patience Is Paper-Thin

Red Sox fans aren’t just passionate — they’re informed. They’ve seen titles. They know what sustained success looks like. And they know what a front office dodge sounds like. You can’t just tell fans to be patient — you have to show them it’s worth it.

A couple savvy signings could help. Maybe a big bat or frontline starter that makes it clear this isn’t just another year of tread-water baseball. But most importantly, the Red Sox need to prove they can get back to building something sustainable — and they’re going to have to do it while earning back a whole lot of trust that’s been lost since the day they let Betts walk.

Lessons from a 5‑Year Free‑Fall

1. Value Your Homegrowns. Waiting until a star is one year from free agency and then trying to play catch-up never works — at least not in Boston’s case. If you don’t act early and confidently, you’re setting yourself up to either overpay out of desperation or watch them walk.

2. Money Talks Louder Than Slogans. Phrases like “strong culture” and “alignment” might sound good in press conferences, but the players see right through them. Top-tier talent isn’t sticking around just for good vibes and leadership quotes. They want to feel wanted — and that means putting real dollars on the table. If you're not willing to compete financially, you're not really competing at all.

3. Communicate Clear Roles — Early. The Devers situation turned into a mess, not because he was unwilling to move positions, but because the message kept changing. One minute he's the third baseman of the future, the next he's asked to DH, then move to first base midseason. If you’re going to ask your franchise guy to shift positions, that needs to be a conversation in the offseason — not something you spring on him in May.

Nomar. Pedro. Tek. Manny. Papi. The connection between the fans and the Red Sox's stars used to feel genuine. Now? It feels like the loyalty is gone.