How the Red Sox Pursued Alex Bregman: Inside Trade Talks

The Boston Red Sox went into the offseason with one thing on their mind: keep Alex Bregman in Boston as the heart of their infield and clubhouse. Instead, they watched him sign a five-year deal with the Chicago Cubs, leaving the Red Sox scrambling for a new plan.

Let’s dig into how Boston lost Bregman, why the Cubs came out on top, and what the Red Sox might do next to fill the gap in both talent and leadership.

Bregman to Chicago: A Franchise-Altering Decision

Alex Bregman’s choice to take a five-year, $175 million contract with the Chicago Cubs made waves across the league. For Boston, it meant more than losing a star—it was a missed shot at locking down their core after Bregman walked away from the last two years and $80 million of his old contract.

The Red Sox thought their offer was strong. They put a five-year, $165 million contract on the table, but the structure told another story.

On paper, the numbers looked close. In reality, the details—especially around guarantees and payment timing—set the two offers apart.

The No-Trade Clause That Changed Everything

Boston refused to include a full no-trade clause, sticking to what they called “organizational policy.” For Bregman, who’s got young kids, stability was non-negotiable.

Chicago offered him that security, and Boston wouldn’t budge. Both teams built in deferred money, but Boston’s version stretched payments over decades, which really cut into the deal’s value now and made the gap even wider.

Why the Cubs Won the Bidding War

From Bregman’s angle, the Cubs’ offer checked every box. He got more money up front, real job security, and total control over his future.

Boston’s proposal sounded “reasonably competitive” inside the front office, but it just didn’t stack up to Chicago’s mix of cash and protection.

The Cubs made a statement by landing Bregman. Their infield looks different now, and their lineup is a lot scarier. They’re clearly aiming to win big.

Infield Domino Effects in Chicago

Bregman’s arrival could put Nico Hoerner on the trade block. Hoerner’s defense and leadership would appeal to Boston, though his lack of power doesn’t really fit what the Red Sox say they want in the middle of their order.

Red Sox Pivot: What Comes Next?

Now that Bregman’s gone, Boston has to rethink its whole infield plan. The name that keeps coming up is Bo Bichette, a dynamic hitter who’d instantly boost their lineup.

The Bichette Dilemma

Bichette won’t come cheap. He’s likely looking for a longer and richer contract than Bregman, which could be a problem for a front office that almost never does long free-agent deals.

Boston hasn’t handed out a free-agent deal longer than three years in recent memory. Meanwhile, teams like the Yankees and Phillies seem totally fine spending at the top of the market.

Shorter-Term and Trade Alternatives

If Boston decides Bichette’s price is too high, other options are out there—each with its own flaws.

• Eugenio Suárez: Brings power, but his defense and age are concerns.
• Isaac Paredes: Fits well at third base, is probably cheaper, and Boston would have him under control for two more years.
• Brendan Donovan: He’s versatile and productive, but would cost more in trade than Paredes.

Paredes and Donovan are both expected to be healthy for spring training, so they’re realistic short-term solutions.

A Defining Moment for Boston’s Front Office

Losing Alex Bregman puts the Red Sox at a real crossroads. Should they break their usual habits and chase a pricey, long-term star like Bichette?

Maybe it makes more sense to hunt for smarter, shorter-term trades instead. Or, honestly, should they just lower expectations and rethink the plan?

Bregman’s exit leaves a gap that won’t be easy to fill. How Boston handles this could set the tone for the roster in 2026 and even change the organization’s entire approach for years.

 
Here is the source article for this story: Details Of Red Sox’ Pursuit Of Alex Bregman