4. Jameson Taillon
The fourth, and in my opinion final spot of the Cubs postseason rotation should go to Jameson Taillon. With Drew Smyly's extreme struggles in recent weeks and rookies Hayden Wesneski and Javier Assad needed in long relief, it would make sense to roll with a four-man squad. And Taillon has been much better recently, going 4-0 in his last five starts with 30.1 innings pitched and a 2.08 ERA in that time.
Taillon does admittedly have a lack of experience in October, which is another reason why he should be going fourth. In 2022, Taillon made one start in the ALCS for the Yankees, where he went 4.1 innings against the Houston Astros and only gave up one earned run. Taillon's continued success down the stretch will be necessary for the team to sustain the bullpen. With Stroman on the IL and Smyly losing his form, the bullpen is getting taxed at a high rate making clean starts for Taillon imperative.