Alex Bregman’s shocking move from Boston to Chicago wasn’t about money or a better roster, but a deeply personal decision that the Red Sox front office completely misread. Sam Kennedy recently left some pointed remarks on Alex’s loyalty towards the Boston side. Turns out that the real reason behind his switch was much more personal. It was far removed from the on-field drama or money haggling, for that matter.

2-times World Series Champion Alex Bregman joined the Red Sox in 2025 after spending 9 years with the Astros. The 2018 All-Star MVP desired to play for the Boston side.

However, Bregman opted out of the contract after a single season and became a free agent. What followed was a smooth transition for the third baseman. Bregman found a better option through the Chicago Cubs and chose a fresh start. 

Alex’s agent, Scott Boras, just appeared on a candid interview for the New York Post Sports. He told Jon Heyman that the 2024 Gold Glove made the decision not as a player. But “primarily as a father and a husband”.

Boras mentioned that all the needs laid out before the teams were focused on personal priorities. This made the decision-making process much less about the diamond and the paycheck. 

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“Alex and Reagan felt, after review of all this, that the Cubs certainly listened to them and included in the contract provisions that allowed them the most favorable treatment for their situation”, Boras said to the interviewers.

The Cubs offered Alex a 5-year contract with a no-trade clause. This deal isn’t just a long-term security for Bregman. It shows his step towards evolving priorities during the most important phase of his career. 

Scott Boras joked about one of Bregman’s children being “the best two-year-old prospect” he has seen. What he actually emphasized is the baseman’s prime concerns. He wanted stability for his family, which is why he chose the no-trade. It accurately shows how Boras understood the importance of a player’s life beyond the field.

Sam Kennedy previously claimed that “If Alex Bregman wanted to be here, ultimately, he’d be here”. Scott Boras explained how it was more than just loyalty toward a team or chasing big paychecks. Boras, just like Bregman, didn’t make any comments on Kennedy. Yet it was clear that Kennedy, even though unintentionally, didn’t capture the whole essence of the scenario. But he isn’t the only one to make a mistake.

The hidden dealbreakers behind Boston’s offers

The Red Sox misread the situation when Bregman claimed to have other offers. Reports suggest that the team simply thought the infielder was trying to bluff his way into a better bargain. They didn’t expect the Cubs to be genuinely interested in Alex.

The way Boston management played it made Bregman realize that “It’s not worth it”, even if they matched Chicago’s offer.

The Cubs went only $10M over the Red Sox, offering $175M for 5 years. The difference in amount didn’t hurt the negotiation as much as the lack of NTC. Bregman always emphasized the no-trade clause. Not bringing it to the fold – that’s where the Red Sox lost him.

Bregman wanted to play in Fenway Park. Any claim that he is unwilling to continue with the Boston side lacks proper ground. Scott Boras made it clear that the reasons were more rooted in his personal priorities. Chicago was the only team that complied with all his desires. 

Boras made the right decision by guiding him to free agency. Bregman might have had to leave a place he wanted to be. But he can ultimately build on what matters most in his life.