Here’s a bold statement: Alex Bregman isn’t just joining the Chicago Cubs—he’s on a mission to bring them a World Series title. But here’s where it gets controversial: can a player with a history tied to the Astros’ sign-stealing scandal truly become a hero in the Windy City? Let’s dive in.
Published at 8:02 pm, January 15, 2026
Jay Cohen, Associated Press
CHICAGO (AP) — Alex Bregman didn’t mince words. For him, family comes first, but a close second is winning baseball games—and lots of them. On Thursday, with his wife, Reagan, and sons, Knox and Bennett, proudly watching from the front row, Bregman explained why he chose the Chicago Cubs in free agency. His priorities were on full display, both in his words and on the back of his new pinstriped jersey, which bore the number 3—a symbol of his quest for a third championship.
And this is the part most people miss: Bregman’s relentless drive to win isn’t just about personal glory. It’s about elevating everyone around him. That’s why the Cubs stepped out of their comfort zone, offering the All-Star third baseman a staggering $175 million, five-year contract. The deal includes a no-trade clause and a whopping $70 million in deferred payments—a financial commitment the Cubs have rarely made, even for stars like Jason Heyward and Jon Lester, who helped secure the 2016 World Series.
“When you make a commitment like this, you want to ensure the player and the person are both exceptional,” said Cubs president of baseball operations Jed Hoyer. “With Alex, we know we’ve got both.”
Hoyer has been tracking Bregman’s career for over a decade, long before the infielder was drafted second overall by Houston in 2015—just one spot behind current Cubs shortstop Dansby Swanson. Now 32, Bregman spent his first nine seasons with the Astros, winning World Series titles in 2017 and 2022. But here’s the kicker: that 2017 title was tarnished by the sign-stealing scandal, which earned Bregman and his teammates widespread criticism. Will Cubs fans look past that? Time will tell.
Bregman was also courted by Chicago before signing a $120 million, three-year deal with Boston last February, which included opt-outs after the first two seasons. “You’d hear stories about his confidence,” Hoyer recalled. When Bregman hit free agency again after a solid season with the Red Sox (.273 average, 18 homers, 62 RBIs), the Cubs pursued him relentlessly. Their persistence resonated with Bregman, who appreciated their commitment not just to him, but to his family.
“From the start, the Cubs made it clear they wanted me here,” Bregman said. “I can’t wait to get to work with this team, build something special, and win a lot of games. This is just the beginning.”
He’s already hitting the ground running. Moments after signing, Bregman requested reports on his new teammates and a meeting with the minor league staff to ensure he’s aligned with the team’s culture. He’s already connected with Swanson, pitcher Jameson Taillon, and outfielders Ian Happ and Pete Crow-Armstrong. This weekend, he’ll meet more players at the team’s annual fan convention.
“The excitement here is palpable,” Bregman said. “Not just from the fans, but from the players too. It’s a great feeling.”
Bregman even stopped by Hoyer’s office to confirm he could play for Team USA in the World Baseball Classic. Hoyer gave his blessing, and Bregman promised to visit the Cubs’ spring training facility in the mornings to stay connected with his new team. “He’s already going above and beyond,” Hoyer noted. “It’s not just about his workouts—he’s fully integrating into the team.”
Bregman joins a Cubs squad that won 92 games last season and made the playoffs for the first time since 2020, only to be eliminated by Milwaukee in the Division Series. Matt Shaw, who played third base last year, may shift to a super-utility role, with Bregman taking over at third. Swanson remains at shortstop, Nico Hoerner at second, and Michael Busch at first. Here’s a thought-provoking question: With Bregman’s arrival, is this Cubs lineup now a World Series contender, or are there still pieces missing?
Shaw, 24, is a versatile athlete who could also see time in the outfield, keeping the infield fresh and healthy. “Matt’s a Gold Glove-caliber defender,” Hoyer said. “I have no doubts about his ability to adapt quickly.”
As Bregman embarks on this new chapter, one thing is clear: he’s not just here to play—he’s here to win. But will his past overshadow his future in Chicago? Let us know what you think in the comments below. The Cubs’ journey with Bregman is just beginning, and it’s sure to be a wild ride.
