Breaking from tradition, the Cubs unleash a surprising spending spree, acquiring major talent and reshaping their roster for a louder season.
One of the biggest complaints from Chicago Cubs fans each offseason is that the team never spends money in free agency.
Outside of signing Dansby Swanson to a massive seven-year, $177 million deal in December of 2022, owner Tom Ricketts has been very careful in spending his money. The Cubs ended the 2025 season with only one player on their roster with a contract above $95 million.
For a team that is in a big market, that simply can’t happen. The Cubs should be in on the top free agents each offseason and should have a good shot to land them with a surplus of money at their disposal.
Well, the Cubs went out of their comfort zone this offseason and did things they don’t usually do. That’s why the 2025 offseason was one of the best all-around offseasons from Chicago’s front office in quite a few years.
The Cubs made two big moves this offseason by trading for Edward Cabrera and signing Alex Bregman to a five-year, $175 million contract. Those two moves were very unlike how the front office usually operates.
President of baseball operations Jed Hoyer has been known to be hesitant to give away top prospects. But he pulled the trigger to acquire Cabrera from the Miami Marlins in exchange for Chicago’s top prospect Owen Caissie.
Then, the Cubs acquired an All-Star in Bregman a few weeks later. They actually outbid both the Boston Red Sox and the Detroit Tigers to sign the third baseman to the third-largest contract in team history. Only Swanson and Jason Heyward (eight-year, $184 million) have signed bigger contracts with Chicago.
But the front office didn’t stop there. They signed veterans like Michael Conforto, Chas McCormick, and Dylan Carlson to bolster the team’s bench depth before the season, and made some unusual moves to revamp the bullpen.
The Cubs signed Hunter Harvey to a one-year, $6 million deal in free agency, which is higher than what they usually spend for relievers in the offseason. The team also signed two relievers to multi-year contracts. Shelby Miller signed a two-year, $2.5 million deal, while Phil Maton signed a two-year, $14.5 million contract.
Those two multi-year contracts are the first time the Cubs have signed a reliever to more than one year since Craig Kimbrel signed a three-year deal with the North Siders during the 2019 season.
The Cubs agreed to deals with 30 different players this offseason while spending the fourth-most money on free agents. They spent more money than the Philadelphia Phillies, New York Yankees, and Boston Red Sox during the 2026 offseason.
That makes this offseason a surprising success for the Cubs front office.