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2. Kyle Hendricks
Next in line in my opinion should be Kyle Hendricks. While Hendricks has shown signs of his former glory this year, he has certainly had his ups and downs. That shouldn't take away from the fact that Hendricks has the most postseason experience on the staff and he has pitched some huge games for the Cubs. Most notably have to be the pennant-clinching game against the Dodgers in the NLCS and Game 7 of the World Series against Cleveland in 2016. The man is cold as ice and never looks out of sorts on the mound, which has made him very successful in October.
The soft-tossing right-hander owns a career postseason ERA of 3.12 over 57.2 innings pitched. Hopefully, he can build on those numbers this year and help usher in the next great Cubs team. Hendricks is the last remaining piece of the World Series-winning core, and he deserves the respect of game 2 in this hypothetical series.