What Will the Cubs’ Postseason Rotation Actually Look Like?

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We’re just a few short weeks away from the start of the MLB postseason. The Chicago Cubs currently hold a record of 81-66. Barring a catastrophic collapse over the final 15 games, they’ll be a playoff team. With the Brewers leading the NL Central by 10 games, though, Chicago will once again have to make its way through the Wild Card round.

The Cubs were in that position last year, and they found success against the San Diego Padres. Chicago took two of three games in the series, and its pitching staff played a major role in getting the job done. They didn’t allow more than three runs in any of the three games. Their NLDS matchup with Milwaukee was a different story, as two of the three games Chicago lost in that series came when its pitching staff struggled to keep Milwaukee's offense in check. If the Cubs are going to make a deep run this time, their staff will have to be at its best. So what might Chicago’s postseason rotation actually look like?

For starters, I think a lot of it depends on who the Cubs draw in the first round. If Chicago gets matched up with a team like the Philadelphia Phillies, Shota Imanaga and Matthew Boyd are probably going to be huge factors. The Phillies have plenty of powerful left-handed bats, including Kyle Schwarber and Bryce Harper, and Chicago could look to play those matchups as much as possible. In that scenario, we could see Boyd get the ball in Game 1, followed by Kevin Gausman in Game 2. That would put Gausman between the two lefties and give the Cubs a veteran right-hander in what could be an elimination game. Then, if necessary, Imanaga could take the ball in Game 3.

The same can probably be said if the Cubs end up matched up with the Braves. A lineup featuring Michael Harris II, Matt Olson and Drake Baldwin as three of its top four hitters is not something any pitching staff should take lightly. Atlanta has the kind of left-handed talent that could make Boyd, Imanaga and David Peterson especially valuable, and I think playing the matchups as aggressively as possible would be the right move. It wouldn’t shock me if Gausman got pushed all the way to Game 3 in that situation.

That would be an unconventional decision. Gausman is arguably the biggest name in Chicago’s rotation, and Clay Holmes has looked the best out of that group in recent weeks. That said, the postseason is all about winning the matchup in front of you. If the Cubs believe Boyd, Imanaga and/or Peterson give them a better chance against a particular lineup, there’s no reason not to lean into that. If the playoffs were to start today, Chicago would be taking on the Phillies. A lot can obviously happen between now and the end of the regular season, and the Wild Card standings can change quickly, but Philadelphia appears to be one of the more likely first-round opponents for the Cubs at the moment.

If that matchup does end up happening, don't be surprised to see Chicago take a left-handed-heavy approach with its rotation. Gausman and Holmes could be starters, but hand off quickly to Peterson or Imanaga—or vice-versa, But that’s far from a sure thing. The Diamondbacks and Padres are both fighting for Wild Card positioning as well, and those lineups present a much different challenge. Both teams have plenty of dangerous right-handed bats, which could change how Chicago decides to construct its rotation. Against those teams, Gausman and Holmes would surely start Games 1 and 2, unless the team has to scramble just to reach the postseason and loses the ability to select their starters for those games.

Should the Cubs make it out of the Wild Card round, I think they would rapidly switch to a more traditional rotation featuring Gausman, Boyd, Imanaga and Holmes. The order could obviously change depending on the opponent, but those four would give Chicago plenty of different looks. They'd need the length those four can provide to get through a five-game series.

Gausman brings veteran experience and strikeout stuff. Boyd, Imanaga and Peterson give the Cubs two left-handed options who could be especially valuable against certain opponents, while Holmes is arguably the most versatile and high-ceiling (but also among the most volatile). The Cubs were aggressive at the deadline because they knew improving the rotation could be the difference between simply reaching the postseason and making a legitimate run once they got there. Now, with October almost here, they have the opportunity to use that depth in whatever way makes the most sense. Now, they have to hope that by the end of Game 162, there's any configuration that makes any at all.