Controversial Cubs Free Agency Decision May Actually Be Smart

The latest update on Chicago Cubs free agency didn't provide the news fans were hoping to hear.

A report from Cubs insider Sahadev Sharma of The Athletic indicated that the Cubs would not be a team heavily pursuing left-handed pitcher Tarik Skubal.

Early reports pointed to the Cubs being heavy favorites for Skubal, with a general belief that the front office was adamant about bringing him in and Jeff Passan of ESPN reporting that the Cubs wanted Skubal "badly."

Now, as the market begins to take shape and the first dominoes of free agency prepare to fall, the Cubs seem destined for the sidelines, unwilling to participate in a bidding war for Skubal that could ultimately land him a contract worth north of $400 million.

Understandably, Cubs fans aren't exactly happy with the early vibes coming out of the front office. Chicago has been hesitant to spend on the same level as the Los Angeles Dodgers and New York Mets in the past. But after watching the Milwaukee Brewers win 103 games in the regular season and capture their first World Series title in franchise history, it's never been more clear that the Cubs have a lot of work to do. And they're already losing a lot to free agency, with players like Kevin Gausman, Clay Holmes, Shota Imanaga, and Matthew Boyd no longer under contract.

"If not now, then when?" It's no doubt a popular question being asked by Cubs fans these days. But the team not being involved in the bidding for Skubal might actually be better for the Cubs than most people realize.

With the four pitchers I just named hitting the open market, the Cubs currently don't have much of a starting rotation to speak of. Ben Brown made just eight starts and pitched 68 innings in 2026 as he battled neck injuries. Justin Steele missed the entire 2026 season recovering from Tommy John surgery. Edward Cabrera was a huge letdown in his first season as a Cub. He also dealt with injury issues, but wasn't very productive when he was on the mound, posting a 5.96 ERA over 80 innings in 2026.

Braxton Garrett had a 7.71 ERA in three MLB starts with the Cubs and Marlins in 2026, but hasn't been a regular MLB starting pitcher since 2023.

And then there's Javier Assad. A reliable option, no doubt, and an underrated one for the Cubs, but Assad is not the pitcher you want headlining your starting rotation. He's not the guy you want to consider your "most reliable arm." And yet, that's exactly what he is for the Cubs.

All of this to say, there's a lot of work that needs to be done, and it's not something that one pitcher like Tarik Skubal would necessarily fix. The Cubs need multiple additions. And while it remains to be seen if they actually get that done, would it be better for Chicago to spend $400 million on Tarik Skubal or repurpose that money to sign Freddy Peralta and Tyler Mahle (or bring back a pitcher like Clay Holmes), and fill the rotation with multiple competent starters?

Unfortunately, this is an offseason that will be difficult to judge until the full picture comes into focus. But as easy as it might be to get upset that the Cubs are choosing not to pursue Skubal, perhaps there's a better plan in place for that money that will better serve the team's needs.

The Cubs are more than one pitcher away from being on the same level as the Brewers. That much has never been more obvious.