How can Cubs complete rotation puzzle?

This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

CHICAGO -- The arrival of the Cubs Convention typically serves as the unofficial countdown to Spring Training for fans of the North Siders. When the opening ceremonies commence at the Sheraton Grand Chicago on Friday night, it will mark roughly one month until pitchers and catchers report.

The group of players who will take the stage and wave to the fans this weekend will likely represent an incomplete picture of what’s to come in 2024. The Cubs still have work to do up and down the roster, including addressing a rotation that looks at least one arm short of an Opening Day cast.

“Writing out your five guys in the rotation, it just feels like those days have gone away,” Cubs president of baseball operations Jed Hoyer said at the Winter Meetings in December. “As an industry, as a team, you just don't do that anymore.”

Last season, the Cubs needed nine starters to get through the campaign (excluding the handful of bullpen days). As things currently stand, Chicago only seems to have three rotation locks: left-hander Justin Steele, right-hander Jameson Taillon and veteran righty Kyle Hendricks.

When Marcus Stroman opted out of his contract and hit free agency, it left a hole in the rotation that Chicago has yet to fill via free agency or trade. There are still quality options in free agency between Stroman, two-time Cy Young winner Blake Snell, lefty Jordan Montgomery and Japanese lefty Shōta Imanaga (who must sign by 4 p.m. CT on Thursday if he is going to make the move to MLB).

Given the makeup of the Cubs’ entire pitching staff -- which has a trio of potential starters or bullpen candidates in Javier Assad, Drew Smyly and Hayden Wesneski -- bringing in rotation help feels imperative. In a recent conversation, Cubs pitching coach Tommy Hottovy said that adding a starter could indeed “help push other guys into bullpen pieces.”

“The more options we have, and the more flexibility that we have going into the season, [it's] always going to be the best way to start the season off,” Hottovy said. “And then things always end up working themselves out.”

Hottovy said he would expect the trio of Assad, Smyly and Wesneski to be stretched out and receive starts during Spring Training, while knowing they could be converted into multi-inning bullpen arms if necessary. All three pitchers had ups and downs within both sides of the pitching staff in 2023.

Coming off his first taste of the Majors, rookie lefty Jordan Wicks will likely stay on a starter routine at the front-end of the season. If it makes more sense deeper into the campaign to transition him to a bullpen role, that may also be a possibility. How the Cubs do end up handling Wicks’ role will be part of the conversations leading up to camp.

“I'm always a fan of just bringing your best guys with you,” Hottovy said of constructing an Opening Day pitching staff. “If he's one of those best guys, you find a way to get them on the team.”

Behind the top three arms, the trio of swing options and Wicks, the Cubs have right-handed prospects Ben Brown (No. 5, per MLB Pipeline) and Caleb Kilian (No. 23) next on the depth chart. Chicago’s top pitching prospect, Cade Horton, is more likely to reach the Majors in 2025, but a promotion this year should not be completely ruled out.

“The hard thing with pitching is you need a lot of it,” Hoyer reminded. “There's a world where those guys come up and have a huge impact, but you also have to realize that you're going to need a lot of guys to get through the season.”