The Alex Bregman Sweepstakes have officially concluded, and the Boston Red Sox weren't the winners. ESPN's Jeff Passan reported on Saturday night that the Chicago Cubs secured the three-time All-Star third baseman on a five-year, $175 million contract, leaving Boston watching one of the most impactful free agents of the offseason walk out of reach.
Already missing out on Pete Alonso and having to settle for Willson Contreras, losing Bregman has made the Red Sox fans start an uproar. Bregman was also one of the biggest offensive names on the market, coming off a .273 season with 18 home runs, 28 doubles, and an .821 OPS in 114 games. Beyond his bat, he brought leadership and postseason experience, precisely the ingredients that many believed Boston needed after years of falling short since 2018, whether that was in the playoffs or not making them at all.
And while watching Bregman walk out the door isn't what Red Sox fans wanted, some silver linings can still be found amid all of the negativity.
Alex Bregman Joining Cubs Is Frustrating for Red Sox Fans
Critics immediately seized on the optics of Boston losing Bregman, especially in the context of last season's handling of Rafael Devers. When the Red Sox signed him in early 2025, it effectively pushed Rafael Devers off third base and into a designated hitter role, one he openly resisted. That essentially ruined the relationship between Devers and the Red Sox to the point where they had to trade him to the San Francisco Giants in mid-June.
A franchise icon and beloved slugger not seen since Big Papi was traded for relatively little in return. Two of those acquisitions, James Tibbs III and Jordan Hicks, were either traded or didn't work out.
Fans now note that, in the end, Boston moved a homegrown franchise cornerstone to make room for a player who is now gone just 11 months later. It's highlighting the inconsistency of this franchise's path. When Breslow took over in late 2023, the Red Sox didn't do much to improve their team. The only notable signing was a risk at first, with Lucas Giolito signing a two-year, $38 million deal after having one of the worst seasons in his career.
But 2024 showed a change of pace. Breslow acquired Garrett Crochet in a big trade with the Chicago White Sox, who had a Cy Young-contending season in 2025, finishing second in the voting behind Tarik Skubal. Then, they signed Bregman for three years, worth $140 million. At first, he loved Boston, and the fans loved him back. However, after not extending him in the middle of the season, it ultimately caused him to reconsider and exercise that opt-out after the season.
Social media has been lighting up with frustration, as many are further questioning whether the front office and ownership truly believed in maximizing their championship window. Comments have been encapsulating the disappointment, essentially talking about Bregman leaving, and now, without Devers, it's like the Red Sox just created a self-inflicted hole at third base.
To be fair, Boston did make a strong offer and reportedly pursued Bregman "aggressively" (h/t @ChrisHenrique) even considering a long-term deal in the $170 million range. But, once again, they were outbid by another team. That competitive market doesn't necessarily reflect Boston's lack of effort; rather, it exposes the limitations of their financial approach in an era where others are willing to spend big to contend.
Still, that's what it used to be with Boston. Bo Bichette has his asking price at reportedly $300 million, but if the Red Sox aren't going to bite on the $175 million for Bregman, what makes anyone think they'll go after him? The hard truth is that's not going to happen, or best-case scenario, they'll get outbid by another team yet again.
Boston Can Still Find Positives in Bregman's Exit
It's more than frustrating to think about how they handled the Bregman-Devers situation, but remember this: the Red Sox still have a top-10 farm system in the league. Marcelo Mayer and Kristian Campbell can fill in the void. It may not be an immediate regression, but both men are hard workers and could report to Spring Training looking better than ever.
Campbell has gained a lot of muscle, and Mayer has been bulking up in the gym with Roman Anthony and Jarren Duran. If anything, they could both make big impacts in that Red Sox lineup. With Roman Anthony returning as well, that lineup could potentially be dangerous.
While it's incredibly frustrating that an established hitter left, there's no choice but to look at the alternatives, and those alternatives can be outstanding. All the while, the Red Sox still have a bright future with Bregman leaving, and it's been stated since July when they halted their extension talks.