As someone who covers the Chicago Cubs and Boston Red Sox for a living — and considers themselves a fan of both teams, though the Cubs will always be my childhood favorite — there is a really complicated mixture of emotions to work through re: the news that Alex Bregman is signing in the Windy City.
We’ll have a lot more on this signing and what it means for the immediate future of the Red Sox, but for now, I’ll just put the spotlight squarely on the man who deserves it: Craig Breslow. The front office chief in Beantown (and former employee of the Cubs), Breslow has done some great work taking the foundation that Chaim Bloom built and bringing it up to the status of a playoff contender. Trading for Garrett Crochet was a brilliant move, and all of the extensions signed by the young core under Breslow’s watch should keep Boston in the October picture for the foreseeable future.
Plus, despite not making any major-league free-agent signings to this point in the offseason, the Red Sox have augmented their lineup (Willson Contreras) and starting rotation (Sonny Gray and Johan Oviedo) via three distinct trades. Each player brings something to the table that the team was previously missing, be it right-handed power (Contreras), an established track record as a frontline starter (Gray), or a big-bodied, right-handed pitcher with elite raw stuff (Oviedo). In a vacuum, those moves make a team that won 89 games in 2025 even better in 2026.
But baseball doesn’t exist in a vacuum. And the Red Sox still haven’t signed a major-league free agent. You can discuss the long-term efficacy of handing a soon-to-be 32-year-old Bregman $35 million per year for the next half-decade, but the Red Sox just got demonstrably worse for the first time since they were eliminated from the playoffs. And you can’t really blame Bregman for taking a huge payday with another big-market contender.
Breslow has made some foolish decisions in his time running the club. I maintain my belief that trading Rafael Devers — who was dealt mainly to accommodate Bregman at the hot corner — was one of them. It’s too early to say if losing the star third baseman will fall into that category, but there is now a real need for urgency in the front office. Bo Bichette remains a reasonable and high-upside replacement option, but at a $300 million asking price, I’m not really sure how that’s a better value than what Bregman just got. Maybe now is the time to trade one of the starting outfielders for an infielder, but that feels like a bad use of resources when the incumbent option was available for just money.
Again, the Red Sox have insulated themselves from a disastrous offseason by completing their aforementioned trades. Plus, there’s always the chance that they sign Bichette, or trade for Ketel Marte or Brendan Donovan. Losing Alex Bregman doesn’t have to be the end of the world.
In the immediate aftermath of watching him dart for Chicago, though, it sure feels like Breslow and company just let their golden goose get away.