The Boston Red Sox entered the offseason with a clear goal: find a top-tier middle-of-the-order bat to pair with Willson Contreras. They wanted to push the lineup closer to contending.
That plan took a hit when Alex Bregman agreed to a five-year, $175 million deal with the Chicago Cubs. Suddenly, Boston had to rethink its entire winter strategy.
Red Sox Lose Their Top Offseason Target
Bregman was the guy Boston really wanted. Inside the organization, folks saw him as the perfect fit—an All-Star with playoff experience, steady production, and the right kind of leadership.
His choice to sign with Chicago didn’t just take away their top target. It also changed the free-agent landscape for a club that already had little room for error.
Boston did make a push. Reports say the Red Sox offered Bregman a five-year, $165 million contract, but it had big deferrals and didn’t include a full no-trade clause.
When you factor in present value, the offer just didn’t stack up to what the Cubs put on the table. Bregman chose the security and flexibility he wanted.
Why Bregman Mattered So Much
Bregman’s impact went way beyond numbers. In his year with Boston, he made the All-Star team and delivered steady production when healthy.
He also became a strong clubhouse presence. For a team trying to move from rebuilding to contending, losing that kind of influence stings.
Boston’s Original Plan Comes Unraveled
The Red Sox came into the winter determined to add another big bat to protect the heart of the lineup. With Contreras at first, Bregman was supposed to anchor the order and solidify the infield.
Now, Plan A is gone. The front office has shown it can adjust, but losing such a perfect fit makes things messy.
Front Office History Suggests a Pivot Is Coming
Boston’s front office has changed course before. Last offseason, they switched from chasing Max Fried to trading for Garrett Crochet.
That kind of flexibility suggests the Sox might get creative again—maybe through trades or by shifting their financial focus.
Free-Agent Alternatives Come With Complications
Bo Bichette could be an option, but Boston would have to outbid heavy hitters like the Phillies and Yankees. That might stretch their payroll more than they’d like.
The other available bats aren’t perfect fits either:
Fit Matters at Fenway Park
Fenway’s quirks reward certain hitters, and Boston’s roster already leans left-handed. Adding another lefty pull hitter doesn’t make much sense right now.
Any new bat has to fit just right, shrinking the pool of good options even more.
Trade Market or Pitching Upgrade?
The Red Sox have looked at several trade candidates, including Ketel Marte, Isaac Paredes, Brendan Donovan, and Eugenio Suárez. But some, like Marte, seem unavailable, so the choices are limited.
Another idea? Shift resources toward pitching:
No Move Truly Replaces Bregman
Pitching upgrades could help the roster, but none actually bring what Bregman did as a middle-order bat and infield anchor.
Sources call the team’s next steps “creative” and “open-minded positionally.” Still, it feels like Boston is reacting now, not really sticking to its original plan.
Here is the source article for this story: Is Bo Bichette Plan B for the Red Sox, or is it something more creative?
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