The Chicago Cubs have already made two significant moves this offseason, acquiring star outfielder Kyle Tucker and reliever Ryan Pressly from the Houston Astros. These moves signal the Cubs’ commitment to competing in 2025, but one key area still needs reinforcement: the starting rotation. While Shota Imanaga emerged as an ace last season, going 15-3 and earning an All-Star nod, the Cubs can’t rely solely on him to lead the staff. Adding another frontline starter would strengthen the rotation and improve their chances of making a deep playoff run.

According to CBS Sports’ Matt Snyder, Jack Flaherty could be the perfect fit. He predicted Chicago would land the potential ace. Flaherty, 29, is coming off a strong season with the Detroit Tigers and Los Angeles Dodgers, posting a 3.17 ERA with 194 strikeouts in 162 innings. He played a key role in the Dodgers’ 2024 World Series run but has yet to secure a long-term deal in free agency. Given Chicago’s financial flexibility and need for a proven arm, the Cubs could capitalize on the opportunity to sign him.

If the Cubs land Flaherty, their rotation could become one of the most formidable in the National League. A trio of Imanaga, Flaherty, and Justin Steele would give Chicago a powerful one-two-three punch, while Jameson Taillon and Matthew Boyd could round out the group. The Cubs would have depth and top-end talent, with Javier Assad and Colin Rea available as swingmen.

With Tucker bolstering the lineup, Pressly stabilizing the bullpen, and Flaherty strengthening the rotation, the Cubs would be in prime position to make the playoffs and contend for a championship. If they want to complete their offseason transformation, signing Flaherty should be the next move.