Imagine a baseball star so driven by the pursuit of victory that he’s willing to wear his ambition on his jersey. That’s Alex Bregman, who recently made waves by signing a staggering $175 million, five-year deal with the Chicago Cubs—a move that’s as bold as it is controversial. But here’s where it gets even more intriguing: Bregman chose the number 3 for his new pinstriped uniform, not just for style, but because he’s dead set on securing his third World Series championship. And this is the part most people miss—his relentless focus on winning isn’t just about personal glory; it’s about elevating every player around him, a trait the Cubs are banking on to reclaim their former glory.
Published at 8:02 pm, January 15, 2026
By Jay Cohen, Associated Press
CHICAGO (AP) — In a heartfelt press conference, Bregman made it clear: his priorities are his family and winning baseball games. With his wife, Reagan, and sons, Knox and Bennett, looking on from the front row, he explained why the Cubs’ offer stood out. But it wasn’t just the money—though the $70 million in deferred payments is a record for the franchise. It was the Cubs’ unwavering pursuit of him, even after he signed a $120 million deal with Boston last year. That persistence, combined with their vision for the future, sealed the deal.
But here’s the controversial part: Bregman’s path to this moment hasn’t been without its blemishes. His 2017 World Series win with the Astros is still shadowed by the sign-stealing scandal, a stain that continues to spark debates among fans. Does his past tarnish his future with the Cubs, or is this a fresh start for a player determined to prove his worth? The Cubs, led by president of baseball operations Jed Hoyer, are betting on the latter. Hoyer has been tracking Bregman’s career for over a decade, long before he was drafted second overall by Houston in 2015, just behind current Cubs shortstop Dansby Swanson.
“When you make a commitment this significant, you want to ensure the player and the person are both exceptional,” Hoyer said. “With Alex, we know we’ve got both.”
Bregman, who turns 32 in March, wasted no time diving into his new role. He’s already requested reports on his teammates and met with the minor league staff to ensure he’s aligned with the team’s culture. He’s connected with Swanson, pitcher Jameson Taillon, and outfielders Ian Happ and Pete Crow-Armstrong, and he’s eager to meet more players at the team’s fan convention this weekend. His proactive approach has Hoyer impressed: “He’s doing things no one’s asked him to do. That’s just how he operates.”
The Cubs, who won 92 games last season and returned to the playoffs for the first time since 2020, are hoping Bregman’s leadership can push them over the top. But what happens to Matt Shaw, last year’s starting third baseman? Hoyer hinted at a super-utility role for Shaw, leveraging his athleticism to keep the infield fresh and versatile. “Matt’s a Gold Glove-caliber player,” Hoyer said. “I have no doubts about his ability to adapt.”
As Bregman prepares to represent Team USA in the World Baseball Classic—with Hoyer’s blessing—he’s already making it clear: he’s not just here to play; he’s here to win. But the question remains: Can he lead the Cubs to their first World Series since 2016, or will his past controversies overshadow his future achievements? Let us know what you think in the comments—is Bregman the missing piece for Chicago, or is this deal too risky?
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