“That made Alex Bregman a little angry,” former Red Sox veteran Alex Bregman reacted when Roman Anthony praised his former teammate after being signed by the Cubs for $175 million and analyzed what went wrong in Boston.

The baseball world is still buzzing from one of the most talked-about free-agent signings of the offseason. When Alex Bregman, the two-time World Series champion and perennial All-Star third baseman, put pen to paper on a massive five-year, $175 million contract with the Chicago Cubs, it marked the end of a highly anticipated courtship with the Boston Red Sox. What many expected to be a homecoming for Bregman in Fenway Park turned into a surprising pivot to the Windy City, leaving Red Sox fans stunned and sparking endless debates about what went wrong in the negotiations.

But the real drama unfolded not just on the contract terms, but in the emotional aftermath, particularly through the words of Boston’s rising superstar, Roman Anthony.

Just days after Bregman’s signing was announced, the young Red Sox outfielder, who has quickly become one of the most exciting talents in the game, took to social media and spoke publicly about his former teammate and mentor. Anthony, the 21-year-old phenom who signed a groundbreaking eight-year, $130 million extension with Boston back in 2025, didn’t hold back in expressing his admiration for Bregman. He credited the veteran for transforming his approach at the plate, praising his leadership in the clubhouse, and highlighting how Bregman’s guidance had been instrumental in his rapid rise through the minors and into the majors.

“Breggy was huge for me,” Anthony reportedly said in one interview clip that circulated widely. “He changed my swing, showed me how to prepare like a pro every single day, and was always there for the young guys. I’ll miss having him around.”

The praise was heartfelt and genuine, coming from a player who had looked up to Bregman during their time together in Boston. Fans and analysts alike saw it as a touching tribute to the veteran who had taken Anthony under his wing. However, Anthony didn’t stop at compliments. In the same series of comments, he offered a candid analysis of why things fell apart for Bregman in Boston.

He pointed to organizational uncertainties, missed opportunities in communication during free agency talks, and what he perceived as a lack of urgency from the front office to secure the star player who had fit so seamlessly into the team’s culture. “We needed him back,” Anthony added. “The way things were handled… it just didn’t feel right. We lost a leader, and that’s on everyone involved.”

Those words hit a nerve. While many interpreted Anthony’s remarks as a passionate defense of his mentor and a frustrated reflection from a young player watching a key piece walk away, they carried an edge that suggested criticism of the Red Sox management. Social media exploded with reactions from fans, some applauding Anthony’s honesty and others worrying that it could create tension within the organization. The comments section under Anthony’s post was filled with heartbroken Sox supporters, many echoing his sentiments and lamenting the missed chance to keep Bregman in Boston.

Bregman, now settling into his new life with the Cubs, didn’t let the moment pass quietly. The veteran infielder, known for his fiery competitiveness and no-nonsense attitude, reacted to Anthony’s statements in a way that caught everyone off guard. In a post on his Instagram story, Bregman reshared a photo of himself and Anthony from their time together, adding a flexed bicep emoji alongside a caption that read something along the lines of playful frustration.

Sources close to the situation described Bregman’s initial response as “a little angry,” not at Anthony personally, but at the implication that Boston’s handling of the situation was the sole reason for his departure. “That made Alex Bregman a little angry,” one insider noted, explaining that the veteran felt the narrative unfairly painted the Red Sox as the only party at fault, when free agency decisions are always multifaceted.

Bregman, who had been courted heavily by Boston, reportedly felt the Red Sox offer fell short in key areas, including guaranteed years and total value compared to Chicago’s aggressive pitch. The Cubs, eager to bolster their lineup with a proven winner, outbid expectations and gave Bregman the security and respect he sought after years of excellence in Houston. Yet Bregman’s reaction showed that the emotional ties to Boston—and especially to players like Anthony—remained strong. In a follow-up message that surfaced later, Bregman sent a direct note to Anthony, reportedly telling the young star, “Keep killing it, kid.

You changed my mind about a lot of things too. Proud of you.” The exchange softened the tone, reminding everyone that the bond between the two transcended team colors.

For Red Sox Nation, the episode has been bittersweet. Anthony’s praise highlighted just how valuable Bregman had become in the clubhouse during his brief but impactful stint in Boston. The veteran had not only contributed on the field with his consistent hitting and elite defense, but he had also mentored a new generation, helping Anthony refine his swing mechanics and mental approach. Insiders within the Red Sox organization have even credited Bregman with being a key factor in Anthony’s breakout performances, calling it “the ultimate compliment” that a player of Bregman’s caliber took such an interest in the prospect.

As Bregman prepares for spring training in Cubs colors, the $175 million investment comes with high expectations. Chicago sees him as the missing piece for contention in the NL Central, bringing leadership, power, and a championship pedigree. Meanwhile, in Boston, Anthony and the young core will have to move forward without their mentor, carrying the lessons he imparted. The saga underscores the harsh realities of free agency—money talks, but emotions linger.

The fallout has fueled discussions across baseball. Was Boston too passive? Did the Cubs overpay? And most poignantly, what does this mean for the relationship between a veteran who gave everything and a young star who still idolizes him? Anthony’s words opened old wounds for Red Sox fans, while Bregman’s reaction revealed that even in departure, the connections remain deep. In a sport defined by constant change, moments like these remind us that the human element—mentorship, respect, and a touch of frustration—endures long after the contracts are signed.