Chicago Cubs: 3 areas the front office must improve this winter

With the offseason officially upon us, attention can now turn to what the Chicago Cubs front office looks to do this winter to improve the team. There have been a number of interesting topics to discuss regarding Jed Hoyer and his plans for free agency this year, but generally most are left up to speculation per usual.

“I think I’ve said repeatedly that we do have financial flexibility. We have money to spend this winter but I think it’s really important that we do that in an intelligent way.”

Here, we have Hoyer laying out what could be a huge plan to spend, spend, spend and there is instant optimism, which is then quickly followed up with more mystery. What does “in an intelligent way” mean? More cost-effective relievers we hope have a breakout season? Or big ticket free agents that would fill a much-needed hole such as in the starting rotation?

Before long, these questions will be answered as the postseason draws to a close. One thing is for sure, there are several key areas in which this financial flexibility could be spent “intelligently.” With an offense that didn’t even do that bad once after the trade deadline, the focus now needs to be primarily elsewhere. Let’s take a look at 3 areas the front office must improve to get the Cubs back into playoff contention next season.

Chicago Cubs: 3 areas to improve this winter – 3. Bullpen

Let’s start off with the bullpen. After a flurry of moves then sent the team’s top three relievers away at the trade deadline in Craig Kimbrel, Andrew Chafin and Ryan Tepera, the Cubs were left with guys that have shown potential but also lacked a solid veteran presence. After Dillon Maples, Codi Heuer and Adrian Sampson, it was mostly guys playing around average or far below.

Once the three-headed monster departed, the bullpen was left with gaping holes or players that started hot and finished poorly. The Cubs will have to improve the back end especially if they are looking to be even remotely competitive in 2022. As it sits, Heuer is mostly in line for closer duties – with Rowan Wick in the mix, as well – but you want to see the front office bring in someone with more experience and dominance in that department.

After Kimbrel struggled mightily with the White Sox, it will be very interesting to see if the South Siders even pick up his 2022 option this winter. If they don’t, the Cubs need to come calling and get their guy back. The differences between the North and South Sides for Kimbrel have been night and day.

He went from having one of his best seasons ever to one of his worst. If there’s something about Wrigley Field and the crowd that gets him going and he just has more success at Wrigley in general, Chicago can look to capitalize by bringing him back into the mix.

Chicago Cubs: 3 areas to improve this winter – 2. Starting Rotation

If you were suddenly expecting the Cubs’ starting rotation to figure something out as the year went on, you’re sitting at home pretty disappointed. Though Justin Steele finished the year on a very high note, tossing seven shutout innings of seven-strikeout, four-hit ball, he was still pulled at only 76 pitches while throwing a gem. This reiterated something we already knew: Steele just doesn’t (at least not yet) have the ability to max out a pitch count near triple-digits. Therefore, when he got into trouble, his outings were mainly 4-5 innings max.

As was the case with Keegan Thompson, who the Cubs continue to have high hopes for. Granted, he has sky-high potential but is yet to put it all together at the big league level. He too has a short leash and saw an average of no more than 3 to 4 innings. These are not numbers the front office can rely on moving forward from their starters. It is almost safer to keep Steele and Thompson as solid pieces in the bullpen or push them to Iowa and really let them get stretched out.

As for the rest of the rotation, Trevor Williams was traded at the deadline and Zach Davies had an incredibly down year after a polar opposite season in 2020. Davies finished with a 5.78 ERA to go along with a 6-12 record. He will test free agency this season and more than likely not receive an offer to reup with the Cubs. Even Kyle Hendricks, who is now the Cubs ace, finished with a 14-7 record but a brutal 4.77 ERA. If the Cubs are looking to spend intelligently, it will be on quality starters to help the rotation. You simply can not have success in Major League Baseball with below -average starting pitching.