Cheap Cubs ownership has left Chicago facing down an impossible offseason

A season that looked so promising at times for the Chicago Cubs ended in a familiar, frustrating fashion, with the team outscored 12-1 in a Wild Card series sweep in San Diego. The Cubs now have four straight winning seasons and have made the playoffs in back-to-back years, but they haven't advanced past the Division Series since 2017.

Fans on the North Side are hoping to see major moves made this offseason in an effort to get them to the next level, but given how owner Tom Ricketts has operated historically, they're likely to be disappointed by what's to come. Based on Ricketts' track record, this winter could be a particularly tough one for Chicago.

Volume of free agents leaves the Cubs with tons of holes

Here's a look at the Cubs players set to hit free agency after the year. The list is lengthy and features tons of key pieces.

For those keeping score at home, this list includes five starting pitchers, their starting catcher, two starting outfielders, their primary DH and a couple of important relievers as well. Some of these players have options for 2027, but most of those options, if not all of them, will be declined by either the player in question or the team.

Even with Cade Horton and Justin Steele making returns from injury and prospects like Josiah Hartshorn and Owen Ayers rising up the ranks, the Cubs will need to use this offseason to fill several holes on their roster. There are a couple of problems, though: First, the team's farm system doesn't have much high-end talent anymore after recent promotions and trades. Second, and most importantly, ownership does not spend enough money for them to even bring this whole core back, let alone improve upon it.

Cubs payroll situation suggests roster won't be as complete as it should be

The Cubs ran a $247 million payroll in 2026, good for the seventh-highest in the sport. That isn't bad by any means, but that's as high as Ricketts has ever gone. A decent chunk of that will come off the books this offseason, but with Alex Bregman, Dansby Swanson, Nico Hoerner and Pete Crow-Armstrong set to make $19 million or more next year, that's already $100 million allocated to four players.

Their projected 2027 payroll is at over $180 million right now, per Spotrac. This includes players with options, so that number should be taken with a grain of salt, but the bottom line here is: How much money will Jed Hoyer have to work with? Keep in mind that players like Suzuki, Gausman and Holmes will likely make around or more than $20 million in 2027 each. Players better than them will cost even more.

This goes to show that simply running back this roster will be nearly impossible. Improving upon it, especially when considering the Cubs' lack of high-end prospect talent, would be even more difficult. All of a sudden, it feels as if Chicago might've already blown their best opportunity to win it all with this core. Ricketts' reluctance to spend like teams like the Dodgers, Mets and Blue Jays has a lot to do with that.

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