The Chicago Cubs have a lot of work to do this offseason, especially after watching their heated division rival win their first World Series in franchise history.

The need for pitching has been talked about ad nauseam since midway through the regular season. Not only was this due to Chicago's lengthy IL, but they simply weren't getting the production they had hoped for from a handful of players. Jed Hoyer also knew that this offseason would be particularly important for his future starting rotation. The Cubs were ready for at least three starters to hit free agency, with the likely chance that two more would be added to the list.

Well, this officially happened on Thursday morning! Jesse Rogers of ESPN reported that both Matthew Boyd and Clay Holmes have turned down their player options to enter free agency. Once again, this was largely expected, but it only further underscores the significant need the Cubs now have on the mound.

Indeed, Boyd and Holmes have joined Shota Imanaga, Kevin Gausman, and David Peterson as free agents. This means their entire starting rotation from the end of the season could be elsewhere in 2027.

The good news for the Cubs is that they are expected to get back both Cade Horton and Justin Steele. The former remains one of their top arms and has real potential to be a front-of-rotation difference-maker. Ben Brown could also earn a starting job after tweaking his approach and posting his best season yet.

The bad news is that all three of those players will be coming off significant injuries, which makes it hard to know how dependable they can be. This is why the Cubs will almost surely seek out several options on the open market, with many thinking they could make a run at some of the best available arms. If one thing is for sure, they will have the money to do so!

Will the Cubs Bring Anyone Back?

While it's expected that the Chicago Cubs will grab some new faces, Jesse Rogers also guessed that at least one or two of their free agents will be brought back. So, who might be at the top of the list?

Matthew Boyd feels like arguably the safest call. He put together another decent season despite some missed time, and there is a good chance the price tag wouldn't be all that high. Will he command some interest around baseball after the last two seasons? Absolutely, but the fact that he's also 35 years old will work against him.

Speaking of which, re-signing Clay Holmes might be the smartest move. The Cubs gave up their No. 2 prospect, Jefferson Rojas, for a chance to bring in the 33-year-old at the trade deadline. To be clear, you never want to re-sign someone merely because of what you gave up, but the fit here does make a lot of sense.

While Holmes never looked fully comfortable after his mid-season move, there is still reason to believe he will be an elite ground-ball pitcher moving forward. And what better arm to pair with Chicago's top-tier interior defense, which will go unchanged this offseason?

The best thing about Holmes is that the Cubs know that he can also be a force in the bullpen, if needed. He was one of baseball's best relievers with the Yankees before turning into a starter. All things considered, this gives us reason to believe he can age somewhat gracefully and transition back into that role.

The last 2026 Cubs starter who feels worth monitoring is David Peterson. Chicago acquired him for very little early in the year, only to watch him record a shocking 3.70 ERA in 15 starts. The plan always seemed to be that he would transition back to the bullpen at some point, but he forced his way into a consistent starting role.

Another very effective ground-ball guy, it might be hard for Jed Hoyer to let Holmes walk. This is particularly true when we consider that he could cost less than both Holmes and Boyd.

Unfortunately, the chance of Shota Imanaga remaining a Cub feels rather low. His home run troubles have been hard to ignore, and there very well may be another team willing to run up the price. If you're the Cubs, you'd rather save that money to go after an ace.

Regardless, we can't rule anything out at this point. The Cubs have a lot of work to do, and free agency always has a way of being pretty unpredictable. Add in a potential lockout, and this specific winter could get pretty darn weird! Stay tuned.