The Boston Red Sox really need to step up their game in the offseason market. They have not signed anyone who could change the game for the Red Sox, but have missed out big time on such players. First, they missed out on Kyle Schwarber and then on Pete Alonso, and now, it could be Alex Bregman.

But Craig Breslow has one more big problem: if he misses out on Bregman, he has to make sure to get Bo Bichette, or else, the 2026 season might end very badly.

“I already wrote mine down… the Mets… I would have sent him to the Mets once again,” said host Chris Rose. And when asked the same question to Trevor Plouffe, he said, “It’s what’s best for the player… Roots in Arizona… Great place to play.”

Boston missed Pete Alonso at $155 million and Kyle Schwarber at $150 million, shrinking middle-order options. Both hitters fit stated needs, yet Baltimore landed Alonso while Schwarber signed elsewhere during December negotiations. That left Boston focused on retaining Alex Bregman, while also monitoring Bo Bichette’s developing market.

Those parallel tracks narrowed flexibility as prices rose and rival clubs advanced talks leaguewide now.

Alex Bregman seeks five to six years near $170 million after opting out of a 3-year deal. In 2025, Bregman hit .273 with 18 homers, contributing to Boston’s 89-73 record in the regular season. Bo Bichette broadened interest by offering second base, after posting 18 homers, 94 RBI, .923 postseason OPS. His defense graded poorly at shortstop, with -13 OAA last season and -28 over five years.

As costs climbed, Arizona and New York entered talks, tightening while Boston weighed Bregman and Bichette. Reports link Arizona to Bregman via payroll flexibility, while the Mets’ interest followed uncertainty around other targets. Boston cannot absorb projected commitments for both players, forcing timing decisions amid accelerating negotiations leaguewide now.

With rivals advancing and prices firming, the window to choose narrows as fans track every update.

Boston has reached the point where patience risks becoming indecision, and Craig Breslow knows it. If Alex Bregman slips to Arizona or New York, Bo Bichette stops being leverage and becomes a necessity. This offseason will be defined not by ambition, but by which phone call Breslow answers first.

If the Red Sox don’t want Alex Bregman, there are team lineup for him

This is how winters tilt power without asking permission. When hesitation creeps in, someone else sharpens the knife and clears space. An infield spot is about to open, Nick is closer to the exit than the quotes admit, and patience is starting to look expensive. That’s where the Red Sox drift and Alex Bregman waits.

Chicago has quietly positioned itself among serious suitors as negotiations around Alex Bregman continue leaguewide. Front offices tracking the market cite contract projections around six years and approximately $150 million. That number reflects consistent production, including a .273 average, .360 on-base, and .462 slugging last season.

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Despite missing time with a quad injury, he still earned an All-Star selection in 2024.

Those metrics explain why the Chicago Cubs view him as a stabilizing presence while chasing the Milwaukee Brewers. Internal comparisons show his 128 OPS+ would clearly outperform Matt Shaw’s 98 in recent evaluations. Roster flexibility also matters, with infield planning accounting for possible departures and positional shifts by 2027.

When Boston hesitates, Chicago rarely does, and Alex Bregman notices the silence immediately around. The Cubs see contracts as timelines, not risks, especially when production already proves durability. If the Red Sox wait longer, the market will decide for them loudly anyway.