Red Sox fans are feeling that familiar, hollow sting again. It’s January 2026, and the Fenway faithful just watched a cornerstone walk out the door for a few million bucks and a piece of paper. Alex Bregman is officially a Chicago Cub, leaving a crater at third base and a lot of pointed questions for the Boston front office.
Honestly, it feels like a bad rerun.
We’ve seen this script. A star player fits the city perfectly, the fans buy the jerseys, the clubhouse leans on his leadership, and then—poof. He’s gone because the team didn't want to go that extra mile. This time, the "extra mile" was specifically a five-year, $175 million deal and a full no-trade clause. Boston reportedly offered around $160 million. In the world of Major League Baseball, that’s basically a rounding error, yet it was enough to let a Gold Glover slide right through their fingers.
The Scott Boras Masterclass (Again)
You can hate the puns. You can hate the late-night press releases. But you cannot deny that Scott Boras just took the Red Sox to school.
Last winter, the market for Bregman was weird. He ended up taking a "bet on yourself" deal with Boston: three years, $120 million, with opt-outs. It was a classic Boras "trampoline" contract. The idea was simple: go to Boston, prove you’re still an elite force, and then jump back into the market to get the long-term security you actually wanted.
Bregman held up his end of the bargain. He hit .273 with an .822 OPS and played elite defense in 2025. He was the "player-coach" that guys like Roman Anthony and Marcelo Mayer looked up to. So, when he opted out this past November, everyone assumed the Red Sox would just pay the man.
Boras knew better. He knew the Red Sox had a "ceiling" they weren't comfortable breaking. While Craig Breslow and the front office were talking about "aggressive offers," Boras was busy finding a team that didn't just want Bregman, but needed him. That team was the Cubs. By the time the news broke on January 10, the Red Sox were left holding a $160 million bag that nobody wanted to take.
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Why the Red Sox Let Him Walk
It wasn't just about the $15 million gap. According to reports from the Boston Globe and MassLive, the sticking point was the no-trade clause.
The Red Sox under the current leadership have been notoriously allergic to "player-friendly" perks that limit their flexibility. They didn't want to be locked in if things went south in year four or five. But here’s the thing: you don’t get guys like Alex Bregman without giving up some control.
The Cubs gave him the five years. They gave him the $175 million (even with $70 million in deferrals to lower the "present value"). And most importantly, they gave him the full no-trade clause.
It’s a massive gamble for Chicago, sure. Bregman will be 32 this spring. But for a Boston team that already traded away Rafael Devers to the Giants last June—a move that still feels like a fever dream—losing Bregman feels like a total abandonment of the "win now" philosophy.
The Rafael Devers Domino Effect
We have to talk about Raffy. The only reason the Red Sox even needed to be "aggressive" with Bregman this winter is because they created a hole at third base themselves.
Last spring, the team forced Devers to move to DH to make room for Bregman's glove. It caused a massive rift. There were meetings in Kansas City with John Henry himself just to smooth things over. Then, in a shocker, they shipped Devers to San Francisco.
The plan was clearly: "Bregman is our guy for the next half-decade."
Except he wasn't. Now, the Red Sox are staring at a 2026 roster that has a glaring lack of star power in the infield. They swapped a franchise icon for a one-year rental and a pile of "flexibility." Flexibility doesn't hit 25 homers or coach up your rookies in the dugout.
What Happens Now?
Boston is in a corner. They are currently the only team in MLB that hasn't signed a major league free agent this winter. That's a terrifying stat for a big-market team in January.
The name everyone is circling is Bo Bichette. He’s younger (27) and has a massive ceiling, but he’s coming off a weird couple of years and he isn't a natural third baseman. If the Red Sox were unwilling to give Bregman $175 million, are they really going to give Bichette the $250 million or $300 million he’s likely seeking?
There are other names floating around:
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- Eugenio Suárez: A short-term power bat, but a massive defensive downgrade.
- Brendan Donovan: A trade target from the Cardinals who Chaim Bloom (now in St. Louis) knows well.
- Isaac Paredes: Another trade option, but the Rays/Cubs aren't usually in the business of doing Boston favors.
The Bottom Line for Red Sox Nation
The "Bregman Era" in Boston lasted exactly one season. It was a good season—114 games of professional at-bats and a Gold Glove—but it ended the way so many Red Sox stories end lately: with the team's accountants winning and the fans losing.
If you're looking for a silver lining, there isn't much of one today. The Red Sox have the prospects, and they have some payroll space, but they lack the one thing a championship team needs: a finished product.
Next Steps for the Front Office:
The Red Sox need to stop "kicking tires" and actually close a deal. Whether it's an overpay for Bo Bichette or a massive trade for a controllable starter like Garrett Crochet, the front office has to prove that the "aggressive" talk isn't just PR. Watch the trade market specifically—with the Cubs now having a logjam with Matt Shaw and Isaac Paredes, there might be a deal to be made there, though it’ll cost the Sox some of that precious "prospect capital" they love so much.
The clock is ticking. Pitchers and catchers report in four weeks. Right now, the hot corner at Fenway is looking awfully cold.