3 Reasons The Cubs Will Beat The Brewers — And 3 Reasons They Won't

Following their three-game win over the San Diego Padres in the National League Wild Card Series, the Chicago Cubs have moved on to the NLDS for the first time since 2017, and a familiar opponent awaits them there.

The Cubs will face their NL Central Division foes the Milwaukee Brewers, who won a Major League-best 97 games this season, the most in franchise history. The two teams on the shores of Lake Michigan have engaged in plenty of spirited regular-season battles over the last two decades, but this is their first time meeting in the postseason.

Chicago manager Craig Counsell is the obvious storyline, in his second year managing the Cubs after spending the previous nine years as the Brewers' skipper. Counsell grew up in the Milwaukee area and played for the Brewers for five years, then took them to the playoffs five times as manager between 2018 and 2023.

The regular-season series between the teams was as even as it gets, with Chicago holding a 7-6 edge. Milwaukee caught fire in July and August, overtaking the Cubs to win the NL Central for the third straight year and secure home-field advantage throughout the playoffs. The series will start Saturday afternoon at American Family Field.

The @Cubs and @Brewers have NEVER faced off in the #Postseason ... until now!

Two NL Central rivals meet with a spot in the NLCS up for grabs! pic.twitter.com/cbsugOWFP9
— MLB (@MLB) October 3, 2025

Here are the ways Chicago can pull off the upset and advance to the NLCS, and the ways the Cubs could fall short and see their season come to an end.

Why the Cubs will beat the Brewers

The extended layoff will hurt Milwaukee

Cubs and Brewers fans at American Family Field — Benny Sieu-Imagn Images

History shows that a postseason bye may not be the gift that it would seem. Since the current playoff format was adopted in 2022, six of the 12 teams to advance directly to the Division Series did not make it past that round.

That said, the Los Angeles Dodgers and New York Yankees were the top seeds in their respective leagues last year and met in the World Series, but anything can happen in a best of five.

Meanwhile, Chicago is energized following an emotional series win over the Padres in which the Cubs held San Diego to just five runs in three games. Travel won't be an issue, as the two ballparks sit less than a two-hour drive apart, and the Cubs often bring legions of fans across the border into Wisconsin.

They've played the Brewers tougher than anyone

The Miami Marlins might beg to differ, but during Milwaukee's historic run that propelled the Brewers from 6.5 games behind the Cubs in mid-June to nine games ahead of them by mid-August, Chicago gave them a harder time than just about any other team.

There are no secrets between the two rosters and coaching staffs, especially after a five-game series in August at Wrigley Field — a series the Cubs won, three games to two.

THE MOMENT. #FlyTheW pic.twitter.com/M5hRqecb6A
— Chicago Cubs (@Cubs) October 3, 2025

Milwaukee had just come off its franchise-record 14-game winning streak when the Brewers headed to Chicago, and after the Cubs dropped the series opener 7-0, they took the next three, including a doubleheader sweep on Aug. 19.

After building a comfortable division lead, Milwaukee was on cruise control in September, going 12-12. It can be a tall task to go straight from relatively meaningless games to the cauldron of a short playoff series, while the Cubs will already have a postseason mindset from their three hard-fought games with the Padres.

The Cubs showed they can make offensive adjustments

Chicago's season might have been over on Wednesday if not for two big swings by Seiya Suzuki and Carson Kelly in Game 1 of the Wild Card series, and San Diego then held the Cubs to four hits in a Game 2 shutout. But although the Cubs scored just three runs in Game 3, their approach at the plate was far better.

Pete Crow-Armstrong, hitless in each of the first two games, was 3-for-4 on Thursday. Kyle Tucker singled twice, Kelly continued to see the ball well and Michael Busch provided a huge insurance run with a solo homer in the seventh inning.

Chicago banged out 13 hits, besting its total from the previous two games combined. The Brewers' arms can match up with any pitching staff in MLB, but the Cubs also have more time to adjust in a slightly longer series.

Why the Cubs won't beat the Brewers

Milwaukee can set up its rotation however it wants

Freddy Peralta — Mark Hoffman/Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

The Brewers had the third-best starting pitching ERA in the regular season at 3.56, behind only the Texas Rangers and Philadelphia Phillies. And unlike Chicago, Milwaukee can line up its starters the way it wants, with Freddy Peralta (17-6, 2.70 ERA in 176 2/3 IP) scheduled to start Game 1.

Brewers manager Pat Murphy has not yet announced his starters beyond Saturday, but Quinn Priester seems like a good bet to take the ball in Game 2. The Chicago area product was traded to Milwaukee from the Boston Red Sox in April and went 13-3 with a 3.32 ERA, and is certainly relishing the chance to beat his hometown team on the October stage. Former Cub Jose Quintana would be lined up to start Game 3 at Wrigley Field.

Behind Quintana, the Brewers have reinforcements, even with Brandon Woodruff unavailable for this series due to a lat injury. Chad Patrick and rookie phenom Jacob Misiorowski can start or pitch in relief.

The Cubs, meanwhile, will have an overtaxed bullpen to start the series, with Andrew Kittredge pitching in all three Wild Card games and several other relievers pitching twice. Matthew Boyd will start Game 1 on short rest, with Javier Assad a candidate to start Game 2 after being left off the Wild Card series roster. Jameson Taillon, Shota Imanaga or former Brewer Colin Rea would then be available for Game 3.

The Brewers' offense will wear down Chicago's pitching

Despite some advanced metrics not loving Milwaukee's offense, the Brewers scored the third-most runs per game in the regular season, and they did so by grinding out at-bats and driving up pitch counts.

KEEP PECKIN@SalFrelick https://t.co/keZdp3Me7N pic.twitter.com/p7BhOxGFVE
— Milwaukee Brewers (@Brewers) August 19, 2025

Sal Frelick, Brice Turang, Caleb Durbin and Isaac Collins may not be household names among casual baseball fans, but they all were above-average hitters despite relatively pedestrian power numbers.

Jackson Chourio battled injuries in his second big-league season but still posted a 112 OPS+ (100 is average). William Contreras and the resurgent Christian Yelich delivered in big spots throughout the year.

Even a four- or five-run lead is not save against this Brewers lineup, which will make the Cubs work for every last out.

This is personal for Milwaukee

Craig Counsell and Pat Murphy — Mark Hoffman / Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

The I-94 rivalry turned spicier than ever when Counsell decided to make the move south to become the highest-paid manager in MLB history. Beloved in Wisconsin for his entire adult life, Counsell has been booed viciously during every Cubs visit to Milwaukee, and many of his former players still sit in the Brewers' dugout.

Milwaukee has certainly not suffered from Counsell's absence, winning division titles in 2024 and 2025. But playoff success has eluded the Brewers, who have never won the World Series and have just two playoff series wins this century. This is their chance to exorcise some demons in more ways than one after proving throughout the regular season that they were the better team.

The Latest Chicago Cubs News