The dust has settled from the most enthralling World Series in ages, which has subsequently led to the outset of an offseason that, in many ways, figures to be just as intriguing as the play on the field. A great deal of speculation has been placed on how Jed Hoyer and his braintrust will build off of a successful 2025 campaign, which brought winning playoff baseball back to Wrigley Field for the first time since 2017.

By now, you know that whatever plans the organization moves forward with will not include left-handed ace and sentimental fan-favorite Shota Imanaga. The 32-year-old hurler just finished his second full year of Major League Baseball in a Cubs uniform, a disappointing campaign for the starter in terms of not just a drop in velocity and victories, but in his club’s confidence in him to go out and get the job done. The show must go on, but hopefully with the right performers to make this heartbreaking turn of events worthwhile. With a flurry of top-flight free-agent pitchers hitting the market as we speak, it’s up to the front office to get this squad’s momentum heading in the right direction.

Might I humbly offer the three most suitable options the club must pursue to ensure that their next act is worthy of ovation. 

Michael King: Over his seven years as a major league pitcher, King has curated the kind of profile that makes him a perfect fit for the Chicago Cubs’ rotation. Like Imanaga, he’s teetering on the wrong side of 30, but he boasts a 3.24 career ERA with 559 punch outs since his debut. Though suffering a stark decline in strikeouts from 2024 to 2025, he features an impressive array of pitches. His go-to pitch, the sinker, pairs well with his other off-speed pitches, leading to a 66th-percentile whiff rate. Along with fellow Padres starter, Dylan Cease, King took an overall step back in 2025 on a team which the Cubs defeated in the Wild Card Round of the 2025 playoffs. A good amount of that can be chalked up to knee and shoulder issues, which may scare off potential suitors this winter.

Even when taking those drawbacks into consideration, King makes sense as a priority target for the Cubs. Pitching coach Tommy Hottovy has a penchant for squeezing every last drop of potential from his pitching staff, and it was just last year that the right-hander looked the part of a staff ace. If he works out, King could be a royal pain for opposing batters to deal with. 

Joe Ryan; In his time wearing a Twins uniform, there’s nothing about this 29-year-old righty’s eye test that screams, “Get this guy to Wrigleyville!” But, the more you examine both his performances and pitch arsenal, he makes sense. The most tantalizing aspect of Ryan’s game is that he’s a certified strike-thrower. Employing his four-seam fastball over 50% of the time, Ryan ranks in the 84th percentile in strikeouts. Perhaps more importantly, he ranks in the 87th percentile in walk rate. If getting guys out by way of the K and not letting them reach base sounds good, Ryan is your man.

Dylan Cease: When you clicked on this article, this was probably the first name you expected to see. Since the Cubs traded Cease to their Southside counterparts in 2017, he’s been one of the game’s premier hurlers. Though he’s fallen on relatively hard times the past two seasons, he’s still got the raw stuff the Cubs have been lacking in their rotation.

Though he only won eight games in 2025 with a 4.55 ERA, he recorded a far more impressive fourth-place finish in Cy Young voting in 2024. And during both seasons, he gave the Padres a whole bunch of innings, spinning 189 1/3 in 2024, and 168.0 in 2025. As the Cubbies have recently done with starters such as elder statesman Matthew Boyd, Cease could experience a resurgence in effectiveness as a member of Craig Counsell‘s squad. Outside of his ties to the city, Cease also features a more balanced pitch selection than some of his fastball-heavy free-agent counterparts. I’m certain that if Cubs fans could prioritize one reunion, it would be with Kyle Schwarber, but, should fortunes allow, Dylan Cease is an individual the whole organization should hold in high regard when it comes to playing for the home team at Wrigley once more. 

This is simply a select few options the North Siders have at their disposal, though in my mind, they figure to be the best. The Chicago Cubs are coming off of a postseason appearance that thrilled us all, but still felt like it was too short. The alchemy of this team is changing, and with the departure of Shota Imanaga heralds the loss of the club’s soul. If this front office seeks to quickly restore it, it had better make its response count.Â