Cubs' Nightmare Route to World Series: Worst Possible Matchups In Every Round

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There are just two weeks remaining in the MLB regular season, meaning the postseason is rapidly approaching and the battles for seeding and home-field advantage are ramping up. That's no exception in the National League Wild Card race, as the Chicago Cubs are battling alongside the Philadelphia Phillies for the fourth seed and home field advantage in the Wild Card Round.

While securing the home field advantage would be massive for the Cubs, it's also fair to assess what a worst-case scenario would look like. The NL field is more or less set (barring a last-minute surge from the Arizona Diamondbacks), so now's the time to try and navigate what a nightmare path to the World Series would look like.

Wild Card Round: Chicago Cubs @ Philadelphia Phillies

The Cubs actually handled the Phillies well in the regular season, winning six out of the seven games between the teams, including a four-game sweep at Wrigley Field. There is a difference, though, between a series in April and a postseason series at Citizens Bank Park. The only team to recently have any success in Philadelphia during the postseason was the Diamondbacks in 2023, when they knocked off the Phillies in seven games to advance to the World Series.

For the Cubs, a Wild Card series in Philadelphia would mean games against Zack Wheeler, Christopher Sanchez and Jesus Luzardo, arguably the best starting trio in the majors. Despite their success twice against Sanchez in the regular season, that is still an intimidating group to face. Those pitchers and that environment would be a nightmare for Chicago in the first round.

National League Division Series: Chicago Cubs vs. Los Angeles Dodgers

Much like Philadelphia, Los Angeles is another team that Chicago normally fairs well against in the regular season. That includes this season, as the Cubs won the season series 4-2 over the Dodgers, including a three-game sweep at Wrigley Field in early August.

Regular season success gets thrown out the window in the postseason, though, and it then becomes a matchup not against a team you had success against in the regular season, but a matchup against the team that is the back-to-back World Series Champions. The combination of a dominant starting rotation and extraordinary lineup that has excellent postseason hitters such as Max Muncy and Freddie Freeman make the Dodgers so hard to knock off. A five-game series may be less of a gauntlet than a seven-game series, but meeting the reigning champs in the NLDS would be a tough matchup for the Cubs.

National League Championship Series: Chicago Cubs vs. Milwaukee Brewers

It feels like it was just yesterday that the Cubs had narrowed the game in the NL Central to just three games. That narrow margin was erased by Milwaukee just as the quick as the Cubs closed the gaps and now, barring an epic collapse, the Brewers will be division champions for a third consecutive season.

We've seen this story before. Chicago can hang around for a while, but the Brewers eventually pull away and show they are the superior team. That was showcased in recent weeks with the two teams splitting a four-game series at Wrigley Field and then the Brewers sweeping the Cubs in a three-game set at American Family Field. The difference in philosophy and pitching talent when the two teams meet up is evident, and if the Cubs can survive a few early October tests, a trip to Milwaukee in the NLCS with a trip to the World Series on the line would be equal parts enthralling and frigthening.