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Just days into spring training, Alex Bregman directly responds to the lingering question about leaving Boston for Chicago. The 2024 Gold Glove winner admitted to being surprised about not going back to the Red Sox. His composed responses to Sam Kennedy’s remarks on loyalty reflect class. Bregman highlighted how the Cubs truly valued what’s important to him.

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Sam Kennedy’s tone-deaf comment, “If Alex Bregman wanted to be here, ultimately he’d be here,” attracted some solid backlash.

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Bregman, however, never attempted to fuel the controversy. Instead, he told Foul Territory how much he enjoyed playing in Fenway and the camaraderie there. Interestingly, there was no bitterness in his voice. Beyond his affection toward his previous team, the reason he chose Chicago was how they valued his needs and priorities.

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“The Cubs really showed that they valued what was important to my wife, me, and our family. I couldn’t be more excited to be able to raise Knox and Bennett in Chicago,” Breggy shared.

The mention of his children shows how important they are to him. His family-first approach clarifies his exit from Boston to be thoughtful rather than abrupt.

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The interviewer pressed on the specifics of whether the no-trade clause was a deciding factor. The 2-time World Series Champion simply avoided giving away any details. Instead, he disclosed a bigger priority.

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“It was really important to be in a place that I felt like I could win. Chicago definitely checked that box,” revealed Bregman.

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The interview highlighted Alex Bregman’s calm, thoughtful, and classy character. That is exactly how we see him on the pitch.

While Bregman stayed measured, his super agent offered a more incisive perspective.

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The Cubs listened to Alex Bregman; the Red Sox didn’t

Scott Boras appeared in an interview a day earlier, and he had to address the same matter.

Bregman’s agent declared that all his needs were communicated to all the clubs. While Boston supposedly maintained a ‘take it or leave it’ stance, Chicago considered Alex’s priorities.

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This is why Alex Bregman was surprised at the beginning of his free agency – that the club he wanted to continue with didn’t engage as deeply as he expected. Boras clearly explained how Bregman’s needs were family-oriented.

The offer made by the Cubs was only slightly better than the amount the Red Sox were ready to spend on him. But for Alex, it was not just about the paycheck.

Both Alex Bregman’s comments and those of his agents established that Sam Kennedy’s remarks were poorly founded. He never really ‘wanted out.’

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Whether it was rigidity or misreading the personal motivations of the player, Boston missed a win here. Bregman is right where he wanted to be, cherishing what’s most important for him.

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Written by

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Ritabrata Chakrabarti

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Ritabrata Chakrabarti is an MLB journalist at EssentiallySports, covering Major League Baseball from the MLB GameDay Desk. With an engineering background that sharpens his analytical lens, he focuses on game development, strategic breakdowns, and league-wide trends that shape the season on a daily basis. With over three years of experience in digital content, Ritabrata has worked across editorial leadership and quality control roles, developing a strong command over accuracy, structure, and storytelling under fast-paced publishing cycles. His MLB reporting goes beyond surface-level analysis, offering fan-oriented explanations of individual and team performances, in-game decisions, and roster moves. Ritabrata closely tracks daily storylines by connecting on-field performances with broader seasonal arcs and offseason activity, helping readers make sense of both the immediate moment and the long view.

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Ahana Chatterjee

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