Where Red Sox's Offseason Went Wrong, According to Insider

An offseason smattered with solid additions for the Boston Red Sox could ultimately be remembered for the one major subtraction.

After trading for Sonny Gray and Willson Contreras, everything seemed teed up for the Red Sox to re-sign three-time All-Star third baseman Alex Bregman. Instead, they lost his bidding war to the Chicago Cubs in early January, as he signed for five years, $175 million on the North Side.

To their credit, the Red Sox quickly pivoted and spent a lot of the money they had bookmarked for Bregman on a five-year, $130 million deal for starting pitcher Ranger Suárez. But there's still a gaping hole on the infield, and it's not entirely clear if and when it will be filled.

If you like our content, choose Sports Illustrated as a preferred source on Google.

Did Red Sox prioritize Bregman too heavily, or not enough?

Jan 12, 2026; Chicago, Illinois, USA; Chicago Cubs third baseman Alex Bregman watches an NHL game between the Chicago Blackhawks and Edmonton Oilers during the third period at United Center. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

On Wednesday, insider Rob Bradford of WEEI dropped a succinct critique of the Red Sox's offseason. According to Bradford, Boston put too many eggs in the Bregman basket to not wind up getting him back, especially when it came to timing.

"There is a lot of good in the Red Sox's offseason, but it is also a great example of how you should do everything in your power to get Plan A (in this case, Bregman) because scrambling for pivots can be problematic," Bradford wrote on X. "There is a reason there are Plan A's."

Had the Red Sox re-signed Bregman, they obviously wouldn't have Suárez, but their infield would be set, and their rotation still would be in a strong position. But the flip side to what Bradford intimated is that they'd be better off had they known a lot sooner that they wouldn't be signing Bregman.

Would Boston have traded for Ketel Marte earlier in the offseason, before they knew he'd be coming off the market? Would they have taken a longer look at Pete Alonso, who still has a lot more power potential than Contreras?

Now, they've forced themselves into the awkward position of being one move away without having a clear path to that move. Either they'll make a very risky trade in the next few weeks, or they'll enter the season with a roster that every fan pans as incomplete.

UPDATE: Chris Cotillo of MassLive reports the Red Sox and utility infielder Isiah Kiner-Falefa are expected to sign a one-year contract, which may further illustrate Bradford's point.

More MLB: Where Red Sox Stand With Isaac Paredes, Nico Hoerner: Insider