With an 8 1/2-game cushion in the National League Wild Card picture. it feels fairly safe to assume that the Chicago Cubs will be playing postseason baseball in 2025, for the first time since the Wild Card series of 2020 against the Miami Marlins—which doesn’t count, and neither does the abortive one-game Wild Card appearance in 2018, so really, since 2017.
The NL Central is still within theoretical reach, with the Milwaukee Brewers losing Trevor Megill, their All-Star closer to the 15-day injured list with a flexor strain. It is most likely, though, that the Cubs will end up securing one of the top two Wild Card spots in the NL and play in the best-of-three first-round series.
When thinking about postseason baseball for the Cubs, the playoff rotation is the first thing that comes to mind. It’s almost a guarantee that in a best-of-three series, Chicago would roll out the trio of Matthew Boyd, Shota Imanaga, and Cade Horton for those three games—assuming they have the luxury of setting their rotation in advance. It is a bit unclear what order those three would pitch in, though, and that ultimately could be decided by the postseason seeding.
The No. 4 overall seed (and top Wild Card seed) would give the Cubs home-field advantage in the first round. That would obviously be the best-case scenario, as the trio of pitchers mentioned above all boast a better ERA at home than they do away from the Friendly Confines. A No. 5 seed would mean Chicago goes on the road, and that is where things could get a bit tricky.
Neither Imanaga nor Horton have ever made a start in the postseason, and there is a slim possibility that manager Craig Counsell does not want that taking place in front of what could be an insane crowd like Philadelpha or San Diego. That could force decisions to start the likes of Jameson Taillon in Game 2 and then decide between Imanaga or Horton for the deciding Game 3 of the series.
Such a move would likely enrage the fan base, especially if it were to backfire. Starting the three best pitchers in the rotation would most likely leave Taillon to pitch Game 1 of the NLDS, if Chicago was able to advance that far.
After that, the postseason inexperience comes right back to bite. Colin Rea has never made a postseason start; neither have Javier Assad or Ben Brown. Boyd and Taillon are the only two members of the starting rotation with postseason experience. That obviously isn’t the end of the world, as we saw the Arizona Diamondbacks nearly win the World Series with little postseason experience on their entire roster.
The lack of experience could make for a nervous postseason for Counsell, and he may feel like he needs to stay away from his inexperienced players. It may get to 2017 Brandon Morrow territory, when Dodgers’ manager Dave Roberts used Morrow in every single game of the World Series. Due to his usage so far this season, Brad Keller seems like the one arm Counsell would continuously turn to.
The Cubs’ staff isn’t the most benighted of the potential playoff teams, but their inexperience is worrisome and that could ultimately lead to poor decision-making—or just poor performance, born of a dearth of reliable options.