Unprompted, a Chicago Cubs player approached a reporter in the Wrigley Field clubhouse after an early-season victory last year and shared an observation: Imagine how good we would be with Bregman.
Alex Bregman was the one who got away, the All-Star third baseman the club tried to sign in spring training with a halfhearted contract proposal that would be rejected.
This time, the Cubs made Bregman an offer he couldn’t refuse.
With Chicago’s sports fans captivated by Da Bears and Saturday night’s wild NFL playoff win over the Green Bay Packers at Soldier Field, the Cubs reintroduced themselves as a major-market force, reaching an agreement with Bregman on a five-year, $175 million contract, according to league sources briefed on the deal.
Given another chance, the Cubs did not wait around until spring training or mess around with a team-friendly offer, hoping that Bregman and his agent, Scott Boras, would eventually run out of options and settle for a below-market deal.
This time, the Cubs made their big move on an electric sports night in Chicago, where the Bears eliminated a historic rival with a thrilling 31-27 comeback victory.
This commitment marks a dramatic shift from Chicago’s lukewarm pursuit last February, when the Ricketts family ownership group authorized team president Jed Hoyer to offer Bregman a four-year, $115 million contract.
Instead, Bregman chose the Boston Red Sox, accepting a three-year, $120 million structure that included a substantial amount of deferred money and the ability to opt-out of the contract after his first season at Fenway Park.
Bregman’s much-anticipated arrival lines up with next weekend’s Cubs Convention, an annual event that sometimes turns into an airing of grievances over the franchise’s lack of spending on the top free agents.
With this winter festival also featuring a 10-year reunion of the 2016 World Series team, Bregman gives Cubs fans and the Chicago media a reason to look forward.
Although he will turn 32 in March, Bregman still lit up the front office’s projection system as a versatile Gold Glove defender and an elite right-handed hitter (.846 career OPS), a profile that should maintain a certain baseline level of performance.
But for an organization that often takes a detached view of talent evaluation and acquisition, this also felt kind of personal, an acknowledgement that intangibles matter.
Throughout the game, Bregman carries a reputation as an exceptional clubhouse leader, someone who sets a strong example for young players and shares valuable information during hitters’ meetings and in the dugout.
Bregman already earned two World Series rings with the Houston Astros, and he has performed on the postseason stage in each of the last nine years, continually adding to his baseball IQ.
In Chicago, Bregman should fit right in with Dansby Swanson, Nico Hoerner and a serious group of players who enjoy studying the intricacies of the game and working on their craft. His preparation and perspective should also benefit young hitters such as Pete Crow-Armstrong and Moisés Ballesteros as they continue to grow into their careers.
With so many key players eligible to become free agents after the 2026 season, Bregman’s presence could also help prevent a talent drain and provide some long-term stability.
Missing out on Bregman last year gnawed at Cubs personnel. Any second-guessing wasn’t a criticism of third baseman Matt Shaw, who performed well as a rookie and may now move around as a super-utility player, adding more depth and flexibility to the roster.
The what-if around Bregman was a recognition of the solid foundation patiently built by the Cubs over a multiyear process, as well as an early sense of the pulsating energy that would return to Wrigley Field last October.
Clearly, the Cubs saw Bregman as their missing piece.