Boston made a real push for Alex Bregman, but Chicago’s $175 million offer exposed the gap between valuation and certainty.
Boston didn’t bow out of the Bregman sweepstakes quietly.
MassLive reported Sunday that according to an industry source, the Red Sox made a legitimate push to keep Bregman in their offseason plans, but they also drew a hard line they weren’t willing to cross.
That line reportedly sat at roughly $162 million in guaranteed money.
Bregman, of course, went well beyond it.
Late Saturday night, the Cubs reportedly finalized a five-year, $175 million deal with the star third baseman - fully guaranteed, no opt-outs, and protected by a full no-trade clause.
It was decisive, aggressive, and ultimately more than Boston was prepared to do.
The Red Sox were willing to go five years. They were willing to push the average annual value north. What they weren’t willing to do was stretch the total guarantee into the range Chicago did - particularly without protections that mattered to them.
In other words:
This wasn’t a case of Boston refusing to engage. It was a case of Boston sticking to its valuation.
And once the Cubs blew past it, the outcome became inevitable.
From the outside, Bregman always looked like the cleanest fit on the board. A right-handed bat. Championship pedigree. A natural answer at third base that didn’t require positional gymnastics or long-term projection. Someone who already showed they worked within this system. Internally, though, the Red Sox treated him less like a necessity and more like an opportunity - one they’d pursue aggressively, but not recklessly.
That distinction matters.
The offer Boston made was competitive in structure, high in AAV, and serious enough to keep them in the conversation late. But Chicago’s proposal checked boxes the Red Sox weren’t willing to match: higher total guarantees, fewer strings, and a level of contractual security that effectively removed all downside for the player.
Bregman took it. Understandably.
Once that happened, the question in Boston shifted quickly from ‘why’ to ‘what now.’
And almost immediately, a familiar name resurfaced.
“The Boston Red Sox will now turn their sights to Bo Bichette,” Bob Nightengale wrote shortly after the deal became public.
Sep 25, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) catches a fly ball hit Toronto Blue Jays center fielder Daulton Varsho (not pictured) during the second inning at Rogers Centre. (John E. Sokolowski/Imagn Images)MORE RED SOX STORIES:
That pivot has been hovering in the background all winter, but Bregman’s departure brings it into sharper focus. Bichette may now be the best pure hitter left available, but he comes with a different set of challenges - ones that test Boston’s roster flexibility more than its wallet alone.
The reported price tag sits north of $300 million, a number that forces the Red Sox to answer two questions at once:
1. How much are they willing to spend?
2. How much uncertainty are they willing to absorb?
Because unlike Bregman, Bichette isn’t a plug-and-play solution.
Trevor Story is locked into either shortstop or second base. First base is accounted for with Triston Casas and Wilson Contreras. Marcelo Mayer may not be a finished product, but the organization has made it clear he’ll enter spring training with a legitimate chance to earn everyday reps somewhere on the infield.
That leaves one opening, and potentially multiple claimants.
Bichette has played shortstop exclusively since debuting in 2019. Asking him to move isn’t impossible, but it’s a significant commitment when paired with a nine-figure contract. And then there’s Kristian Campbell, the wildcard whose stock dipped last season but who was a top-five prospect in the sport not long ago. A strong spring could complicate things further.
This is where the Bregman decision comes into clearer view.
Boston wasn’t unwilling to spend. They were unwilling to spend without clarity.
Bregman offered certainty. The Cubs paid for it. The Red Sox valued it - just not at $175 million.
Now, with that option gone, Boston finds itself weighing a different kind of gamble.
Bichette’s bat is undeniable. His fit is anything but clean. And pursuing him would mean letting the roster sort itself out around the talent, rather than the other way around.
That’s a bigger philosophical shift than simply losing a third baseman.
The Red Sox didn’t lose Alex Bregman because they didn’t try.
They lost him because they decided where the line was, and refused to pretend it didn’t exist.
What comes next will tell us how flexible that line really is.
Feb 23, 2025; Fort Myers, Florida, USA; Boston Red Sox infielder Alex Bregman (2) connects with the ball for a double in the fourth inning of their game against the Toronto Blue Jays at JetBlue Park at Fenway South. (Chris Tilley/Imagn Images)JOIN THE CONVERSATION:
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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.