4 areas of need the Chicago Cubs must invest in this winter

In the third full year of Jed Hoyer's "not-a-rebuild," the Chicago Cubs still have significant flaws and are likely to miss the postseason for their fourth straight year. Their last time playing October baseball came in the pandemic-shortened 2020 season, and before that, they made a brief yet disappointing appearance in the Wild Card against the Rockies in 2018. It's been a frustrating stretch for fans and too long for a big market team of this caliber to accept another era of "retooling."

Friction is forming in the front office as Hoyer faces increased pressure to field a winning team in his final season under contract. 2025 will be make-or-break for him and the Cubs as they look to finally return to contention. They have solid pieces all around, but not enough consistency to hang with the great, or even the merely good teams in the National League throughout an entire season. Even with a bevy of impressive prospects knocking at the door like Owen Caissie, Cade Horton, and Matt Shaw, they'll have to make some strategic external additions to bring this team up to snuff.

Although the Cubs ended up above the luxury tax this year, they could have as much as $90 million coming off the books assuming Cody Bellinger opts out. That leaves room for upgrades across the board, even if they're not willing to approach the top of the market. Let's look at four spots that need the most attention in the offseason.

1. The starting rotation needs extra depth

As the old saying goes, you can never have enough pitching. The Cubs learned that first-hand this year as they dealt with injuries to nearly everyone from Justin Steele and Javier Assad to Jordan Wicks and Ben Brown. Although they have plenty of promising young starters waiting in the wings, they've all been prone to injuries and can't necessarily be trusted to immediately cover. Compounding that problem is Horton, their top pitching prospect whose 2024 season was essentially a wash.

This is all without considering the impending departure of Kyle Hendricks. The former World Series hero has struggled mightily this year with a 6.51 ERA, likely spelling the end of his Cubs tenure as he hits free agency. Steele and Shota Imanaga are a phenomenal pair at the top and Jameson Taillon has proven to be a solid middle-to-back end rotation piece, but past them and arguably Assad, there's some flexibility to play with.

A run at Corbin Burnes isn't likely given Hoyer's track record, but with an offseason so packed with pitching, there are options to add some depth to this group at a reasonable cost. Jack Flaherty was loosely connected to the Cubs at the trade deadline and would be a pricier, but intriguing option considering his 2.86 ERA thus far between the Dodgers and Tigers. Nathan Eovaldi, Walker Buehler, and Luis Severino all represent options that have high upside and valuable experience, yet could still take smaller deals for one reason or another.

Even if they don't shop in the luxury aisle, there's bound to be a quality pitcher who falls through the cracks that the Cubs can scoop up for extra depth. The rotation may have been a strength in 2024, but they should push for more in 2025.