Cubs Sign Bregman; Bears Make Playoff Return
On Saturday night, the Bears made a spectacular return to the NFL playoffs, while the Cubs secured a major signing by bringing in Alex Bregman.
Bregman, who is 31, seemed eager to celebrate his new contract. His wife, Regan, shared a cheerful photo of him on Instagram shortly after the announcement of his five-year deal worth $175 million, effectively removing one of the top free agents from the market.
“I’m so proud of you,” Bregman wrote, including a heart emoji and a snapshot of her raising a margarita in toast.
The decision to part ways with Boston came down to a couple of key factors: the promise of a no-trade clause in his new contract and deferred payments. Reports indicate the Red Sox made a strong offer of five years at $165 million, but their unwillingness to include a full no-trade clause was a dealbreaker—something the Cubs provided.
According to sources, Bregman’s agreement with the Cubs involves $70 million in deferred payments, with an average annual value around $30 to $31 million.
Boston showed interest in making a similar deal, but complications arose from their proposed deferral terms, as pointed out by observers.
“The ball is in his court,” said Red Sox manager Alex Cora just hours before the contract was finalized.
Bregman, after signing a three-year, $120 million contract with an opt-out option following each season, hit the open market after just one year in Boston. In 2025, he posted a .273 batting average with 18 home runs, but his season was reduced to 114 games due to a strained quadriceps.
Now, joining the Cubs for his third team in as many seasons, Bregman is expected to strengthen Chicago’s batting lineup, a much-needed lift as they eye other high-profile free agents like Bo Bichette and Cody Bellinger.
Despite those injury concerns, Bregman’s arrival coincides with a fantastic night for Chicago sports. The Bears staged an exhilarating 18-point comeback against the Packers in their NFC Wild Card game, marking a triumphant return to the postseason.
Bregman even acknowledged the Bears’ victory by posting a “Da Bears” flag on his Instagram Story, a fun nod to the team’s success.
Cubs general manager Carter Hawkins reflected on the timing of Bregman’s signing as the Bears celebrated their win. “You know, you never do business with everyone in the office at 3 p.m. on a Tuesday,” he remarked, without directly naming Bregman since the deal hadn’t yet been made official. “It always feels like a Saturday night filled with excitement, whether it’s my anniversary or a holiday, or some other thrilling sports event happening.”
He added, “We want to keep improving our team. Adding quality players is a key step to ensure we remain competitive through the end of October, and we have a wealth of great options.”
