The Boston Red Sox are getting closer and closer to making the big signing that the whole of Boston is waiting for. But amid this news of Pete Alonso becoming the primary target for Boston, fans are now questioning what happened to Alex Bregman and the news of bringing him back?

When the offseason started, we all knew the Red Sox would go after Pete Alonso. And as confirmed by SNY, “The Red Sox reportedly have Pete Alonso as a ‘primary target’.”

But the fact that they have put Pete Alonso ahead of Bregman points to one thing: John Henry and the Red Sox might not be ready to spend big bucks.

The Boston Red Sox have made Pete Alonso their primary offseason target this winter. Alonso opted out of his Mets contract worth $24 million for 2025, entering free agency. Analysts project he could earn a deal around 7 years, $210 million on the open market. Signing him would add middle-of-the-order power to a lineup that finished 15th in home runs.

Pete Alonso’s bat could protect other hitters and improve Boston’s overall offensive output immediately. The Red Sox finished with a .745 OPS last season, slightly above the league average. The team also needs more stability after shedding roughly $400 million in payroll recently.

Without investing more, adding Alonso alone can’t cover the batting needs. And that is where they need Alex Bregman.

Alex Bregman remains a central consideration for Boston, especially after contributing significantly in 2025. Bregman’s leadership and guidance with young players like Ceddanne Rafaela have made him crucial in the clubhouse.

But with the Red Sox keeping Bregman away from now might cause problems. The Chicago Cubs are already looking at Bregman like dinner. After failing to sign him before the 2025 season, the Cubs are not wasting much time in going after Bregman. With them rumored to lose Kyke Tucker, they will need an experienced bat, and Bregman gives them that.

Boston is watching anxiously as Alonso’s signing could define the team’s offensive identity. Bregman’s absence might turn a strong lineup into a patchwork, giving the Cubs a clear advantage. If the Red Sox hesitate, John Henry may discover patience isn’t a virtue when talent slips away.

Why Alex Bregman to the Chicago Cubs makes sense

If baseball had a “what could go wrong?” meter, Boston’s offseason gamble on Alex Bregman would be ticking loudly. The Red Sox got a taste of his bat, but the Cubs are circling like a team that read the fine print on talent and budgets. It’s a high-stakes game of musical chairs, and Bregman might just change the seating chart.

The Chicago Cubs face a critical void after Kyle Tucker’s likely departure from their lineup. Alex Bregman, a 3B who posted 3.5 WAR with a .356 wOBA in 2025, fits that gap. His 18 home runs and 64 runs scored across 114 games show consistent offensive contribution.

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Bregman’s presence would strengthen the Cubs’ defense, complementing their existing infield alignment effectively.

Financially, the Cubs have $50–60 million available for free-agent signings without surpassing the $245 million luxury tax. MLBTR projects Bregman could earn $160 million over six years, which aligns with the team’s budget flexibility. Acquiring him could replace Tucker’s production while keeping lineup stability and infield reliability intact.

If the Cubs land Alex Bregman, their infield instantly transforms into baseball’s most calculated upgrade. Fans will watch Boston’s gamble become Chicago’s opportunity, turning speculation into tangible lineup strength. Bregman’s signing could rewrite the offseason narrative, proving dollars and strategy still outshine mere hype.