The third baseman was asked about his free agency decision during a recent interview with MLB Network. For Bregman, the Cubs’ potential to win was among the elements of the situation that caught his attention.

“I think first and foremost, they valued what we valued, me and my family,” Bregman said. “I think it’s a great place that I have a chance to win, I think this ball club is primed and ready. Obviously they were in the playoffs last year. These guys know what it takes to win. I feel like we have a good opportunity to win a lot of baseball games, hopefully play some meaningful baseball in October.”

Bregman, a three-time All-Star, played with the Houston Astros from 2016-2024 before ending up with the Boston Red Sox in 2025. After just one season in Boston, Bregman signed with the Cubs this past offseason.

Bregman’s leadership prowess was a common subject of discussion in Boston. As a result, some felt that a reunion would make sense. His leadership will prove to be important for a Cubs team that is looking to win the World Series for the first time since 2016.

Bregman is a two-time champion, so he knows a thing or two about getting the job done in the Fall Classic.