The Chicago Cubs’ signing of third baseman Alex Bregman marks the third-largest contract in team history while also representing a long-awaited breakthrough on the free agency market.
What a night it was in Chicago.
While the entire city had their eyes glued to Saturday’s NFC Wild Card duel between the Green Bay Packers and Chicago Bears, the Cubs’ front office picked perhaps the perfect time to make their biggest strike on the free agency market in several years.
Just as the Bears were beginning their momentous comeback at Soldier Field against the Packers, multiple reports surfaced that the Cubs were the team to land All-Star third baseman Alex Bregman, doing so with a five-year deal worth $175 million.
The contract also features plenty of deferred money, an interesting wrinkle to the contract given the Cubs’ previous hesitancy to feature deferred payments in any long-term deal.
The signing is the largest splash the Cubs have made on the free agency market since their signing of Dansby Swanson ahead of the 2023 season, inking a seven-year, $177 million pact with the shortstop at the time.
The Cubs signing Bregman also sends a clear message that the North Siders are trying to build on their 2025 playoff run with another competitive team, something that was at least mildly in doubt given the expiring contracts of Ian Happ, Nico Hoerner, Seiya Suzuki and Jameson Taillon.
The addition of Bregman does introduce the possibility of another infield transaction this offseason for the Cubs, with the current orientation being Michael Busch and Bregman at the corners while maintaining Hoerner and Swanson up the middle.
This leaves sophomore Matt Shaw out of the picture in the starting lineup, who played the majority of his rookie season as the Cubs’ starting third baseman, posting excellent defensive metrics alongside more underwhelming numbers at the plate.
Bregman is an emphatic improvement over Shaw offensively, with the to-be 32-year-old still holding his own defensively. Bregman has managed 28 outs above average in his MLB career, still posting above-average metrics with the Boston Red Sox in 2025 while only being two years removed from an 8 OAA campaign with the Astros in 2024.
While the Cubs could certainly just hang on to Shaw and utilize him as a super-utility player and/or insurance policy for an injured infielder, some have floated the possibility of trading away Hoerner and moving to Shaw to second base, a suggestion I remain vehemently opposed to.
Though Hoerner would undoubtedly command a solid return on the trade market, the Cubs would also be parting ways with their most valuable player of 2025, an elite defensive middle infielder with some of the best contact hitting skills in all of baseball.
Hoerner posted a career-high 6.2 WAR in 2025, part of compiling a wildly impressive 19.6 WAR over the past four seasons, dating back to his first full season as a full-time player. While the power hitting expectations for Shaw would surely decrease if he were to be moved to second base, his profile offensively would not at all replace Hoerner’s contributions.
This is of course before even mentioning the inevitable distraction Shaw has invited onto himself and the team at-large, thanks to his association with the current regime under the guise of “faith” and an appearance at what could most generously be considered a white nationalist convention.
Shaw’s appearance at a Turning Point USA event this offseason came months after missing a game in the heat of a pennant race to attend the “funeral” of slain far-right activist Charlie Kirk – which turned out to be much more of a fascism pep rally than it was a funeral.
The association has expectedly upset plenty of fans, something the team will likely see for themselves at the upcoming Cubs Convention – where fans will also likely express their disappointment with the invitation of Addison Russell, who served a lengthy suspension in 2019 following an investigation into allegations of domestic abuse.
With that said, it’s fair to assume that Shaw’s mingling with the same far-right movement that has created a police state carrying out kidnappings and extrajudicial killings is not a dealbreaker for the Cubs, who will likely entertain a trade for Shaw if they deem the price and fit to be in line with the team’s future with Bregman.
Assuming the Cubs don’t trade Hoerner, the 2026 season poses a fantastic opportunity for the North Siders to finally win the NL Central in a full season for the first time since 2017, with the team’s projected infield providing a helpful boost in a rather unremarkable division.
The Bregman signing is of course the second significant move the Cubs have made just this year already, trading the club’s top prospect in Owen Caissie to the Miami Marlins in exchange for hard-throwing righty starter Edward Cabrera, shoring up the club’s rotation.
Though one would be especially foolish to believe the Milwaukee Brewers couldn’t compete all year long and win the division yet again, the Cubs finally made a long-awaited signing that lives up to their status as a big market team – a team that should be in the conversation for most big free agents.
While Bregman’s deal is still beneath the overall value of Swanson’s deal and the $184 million contract Jason Heyward signed in December 2015, the $175 million commitment over five years with a no-trade clause and no opt-outs represents an uncharacteristic commitment from the Cubs’ front office that many fans, myself included, were yearning for.
That’s not to say the Bregman deal is without risk, as it is ultimately a long-term deal for a player already two seasons into his 30s, but the fit and pedigree were simply too much for the Cubs to ignore. In Bregman is a seasoned two-time World Series champion, a proven playoff performer who is capable of being among the league’s most productive hitters when healthy and at his best.
While it would be naive to believe Bregman is going to replicate his 2019 numbers that earned him AL MVP runner-up status, it’s fair to assume that a healthy Bregman means a noticeable improvement at third base.
Despite battling through injuries through parts of 2025, Bregman still managed a 128 OPS+ with 28 doubles and 18 home runs, numbers that were surprisingly not boosted by Fenway Park as the slugger managed an .875 OPS on the road.
In Bregman, the Cubs maintain solid defense at third base while adding another formidable power hitter to a lineup that already features Seiya Suzuki, Pete Crow-Armstrong, Michael Busch and Ian Happ. With this likely being the significant free agency move for the Cubs this offseason, they have defied rumors of going through a lame duck 2026 season with expiring contracts and a looming lockout by finally striking big on the free agency market.
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