Chicago Cubs Need To Prioritize Starting Pitching Depth This Winter

The Cubs are coming off of a very good 2025 season, arguably their most successful year in close to a decade. They won more than 90 games for the first time in seven years, and for the first time since 2017, they advanced past the first round of the playoffs. There will be some notable changes to the roster next year – like Kyle Tucker heading to free agency – but the Cubs need to use this offseason to build on last year’s success and get even better. The best way to do that is by prioritizing starting pitching depth.

There are other needs, like rebuilding the back of the bullpen, and the Cubs have taken some steps toward addressing those, but the starting rotation showed in 2025 the need for more arms. Cubs team president Jed Hoyer told reporters in early November that his priority this offseason will be on pitching, especially given that the offensive side of the team is pretty well set.

Hoyer also said that the Cubs won’t necessarily limit themselves to adding pitching via free agency.

“You have to explore everything,” Hoyer told reporters. “And we’re not just going to focus on the free-agent market with pitching. I think we’ll probably look at the trade market. It may come to fruition, it may not, whereas we’re going to sign some free agents. I think there’s no question. The trade market? We don’t know yet.”

At this early stage of the offseason, the free agent market has favored starting pitchers, so the Cubs will need to be aggressive if they are going to keep pace with teams at the top of the market. They will also need to be willing to open up the pocketbook if Dylan Cease’s seven year, $210 million deal with the Blue Jays is any indicator of how the pitchers’ market is going to go.

This, of course, assumes they aren’t able to add via trade, but as Hoyer said at the general managers’ meetings, that is not an option that’s off the table. The Cubs have the organizational depth – especially on offense – to swing at least one deal for a starting pitcher, but the fact that Tucker is gone does mean they will need some of that depth to help fill the void in right field.

With that in mind, free agency remains the most likely avenue for bolstering the Cubs’ starting rotation. The good news is the Cubs don’t have tremendous need. As things currently stand, they will go into 2026 with Matt Boyd, Jameson Taillon, Shota Imanaga, and Cade Horton all set to take rotation spots. They should also see the return of Justin Steele at some point in the first half of the season, so this isn’t a situation where the Cubs have a glaring vacancy in their staff.

That said, Boyd was the only member of last year’s rotation to not miss a start, and his performance dipped in the final weeks of the season – possibly because of the heavy workload – so it is clear that the Cubs need more starting pitching depth for next season. Ideally, the rotation stays healthy in 2026, but past precedent does not point in favor of that happening.

Even with Cease off the board, there are still good options for the Cubs to pursue. Padres starter Michael King would come with injury concerns of his own, but his ability to pitch to soft contact would play really nicely with the Cubs defense behind him. The same could be said of Phillies starter Ranger Suarez, and though Astros starter Framber Valdez wouldn’t come with the same kinds of question marks about his health, the Cubs would have to consider what appeared like him intentionally hitting his catcher after a cross-up against the Yankees in early September. Finally, there’s Japanese starter Tatsuya Imai, who would bring much-needed velocity to the Cubs rotation, but there’s always the newcomer variable to consider when a player comes over from the NPB.

According to Spotrac’s current projections, the Cubs should have just over $70 million in luxury tax space, so they could afford a contract with the average annual value that Cease got from Toronto. The good news is that none of the aforementioned pitchers should cost as much as Cease.

The one thing the Cubs cannot do is stand pat while the other top free agent pitchers sign with other teams. They have a strong rotation already, but repeating last year’s success is going to take depth from the starting pitching staff. And if the Cubs want to do more than just replicate a 92-win season and a wild card berth in 2026, then they need to assert themselves in the free agent market this offseason and add depth to their starting rotation.