Brewers' arch-rival reportedly interested in adding All-Star free agent infielder

Much of the focus atop the National League Central this offseason has been on pitching. The Milwaukee Brewers and Chicago Cubs, who finished first and second (in that order) in the division in 2025, have each already made several decisions in regard to their 2026 pitching staffs during the first month of the offseason. The Brewers, already balancing the decision of whether or not to trade Freddy Peralta before his final season under contract, decided to extend the qualifying offer to fan favorite Brandon Woodruff, who accepted, committing to join Milwaukee's starting staff for another season.

Chicago, meanwhile, made a series of decisions regarding starting southpaw Shota Imanaga, that ultimately led to him too accepting the $22.025 qualifying offer for the 2026 season. The Cubs' President of Baseball Operations, Jed Hoyer, followed that move by signing reliever Phil Maton to a two-year, $14.5 million deal, kickstarting Chicago's anticipated offseason bullpen makeover.

Despite expecting to lose impact bat Kyle Tucker to a higher bidder this winter, there had been no word of the Cubs pursuing position players this offseason until one familiar rumor surfaced on Thursday afternoon. The Cubs, less than a year after they heavily pursued him in free agency, are once again interested in adding now-3x All-Star, Alex Bregman, as reported by Patrick Mooney and Sahadev Sharma of The Athletic.

According to The Athletic, the Chicago Cubs are interested in signing Alex Bregman this offseason

Supposedly, last offseason, the Cubs offered Bregman a four-year deal worth roughly $120 million. The long-time Houston Astro ended up earning a contract worth the same amount of money, but in one less year with the Boston Red Sox. However, included in that contract was an opt-out after the first year, allowing Bregman to once again test the free agency waters this offseason, after putting together a 2025 campaign that should earn him a long-term deal.

Various outlets have predicted different contract numbers for Bregman this offseason, but it's expected that he will earn a 4-6 year deal worth roughly $30 million per season, with that number decreasing as the number of years increases. It's no doubt a hefty price tag for an aging veteran on the wrong side of 30, but Bregman is the type of impact player who is worth sacrificing years of value at the end of his contract for several years of All-Star caliber play at the beginning of his deal.

Meanwhile, while Bregman is no doubt an impact player who would reshape the Cubs' offense in the wake of Kyle Tucker, there's reason to believe that he's not quite the player he used to be. Since his MVP runner-up season in 2019 and not including the shortened 2020 season, Bregman has posted an aggregate OPS of .799 over his last five seasons. While he's always had good plate discipline, his underlying metrics tell a story of a player who is extremely dependent on pull-side power, something that should decrease as the next contract he signs plays out. His glove at third base remains strong, despite his arm strength being below average, as it has been throughout his career.

However, aging curves aside, where Bregman really thrives is in the clubhouse. A perennial winner as a part of the Houston Astros, Bregman won two World Series titles (one with a big asterisk) during his time in Texas. Then, after joining a Red Sox team in a three-year playoff drought, a rare occurrence for Boston this century, Bregman led his team to a playoff appearance in what could be his lone season with the club.

On paper, the move makes enough sense for its potential to worry Brewers fans. The Cubs, who have money to spend if their ownership chooses to do so, could shift Matt Shaw to a utility infielder role in 2026, before slotting him in at second base if Nico Hoerner leaves in free agency a year from now. There's no doubt adding Bregman to that infield group would increase Chicago's chances of dethroning Milwaukee in the NL Central, but concerns still exist with giving the 10-year MLB veteran a deal north of $150 million. Additionally, say what you will about Bregman, but in his current form he certainly isn't a one-for-one replacement for Kyle Tucker's offensive production, and the Brew Crew was able to handle a Tucker-led squad in 2025. Who's to say they won't find that same success in the division with Bregman headlining stories in Chicago?