3 Keys for Milwaukee Brewers to Take Down Chicago Cubs This Weekend

The Brewers wrapped up a dismal road trip with two days of competent—if not outright strong—play against the White Sox, only for the South Siders to usher in May with a humiliating loss for the Crew. Chicago’s -32 run differential will get an eight-point boost when the stats update Friday morning—each of those runs unanswered by a Milwaukee lineup that looked utterly befuddled at the plate in Thursday’s blowout.

That number might have been halved if not for a Herculean grab by Luis Robert Jr., who robbed Rhys Hoskins of a grand slam. But even if that ball had cleared the fence, the Brewers still would’ve needed four more to tie.

Still, Milwaukee took the series, winning two of three from the rebuilding White Sox and returning home with a .500 record. They’re 9-4 at home, but they’d be wise not to exhale just yet: the other, far more dangerous Chicago team arrives next. Yes, the dreaded Cubs make their first visit to Milwaukee in 2025—and they’re coming loaded for bear (pun intended). The offseason moves by the Cubbies have proven to be a boon. Former Astro Kyle Tucker was traded in his contract year for, among others, Chicago’s number one draft pick in 2024, promising right fielder Cam Smith. Tucker is rewarding the Cubs for their expense by being the offensive powerhouse he’s proven himself capable of being over the last several years, already going yard eight times and swiping eight bags. 

Somehow, though, it isn’t Tucker who owns the lead for WAR on the Cubs. That title would belong to defensive wünderkind Pete Crow-Armstrong. All five tools have come to life for the youngster, who exceeded his rookie limits last year. Back then, Crow-Armstrong slugged 10 homers in 410 plate appearances. This year, he’s already hit six in just 120. His speed, however, could be argued to be his most lethal asset. He’ll steal a bag—and, in fact, already has 12 times so far this year—but where he really shines is in his dominance in center field. He ranks in the 95th percentile in sprint speed, recently covering 48 feet in 3.3 seconds to steal a softly hit ball from Tommy Edman. He currently possesses 14 outs above average, good for fifth in the league.

The Cubs are so domineering this year that it feels like a flicker of the headline that it used to be that Craig Counsell is their skipper. Truthfully, the stakes feel too high in this series for sentimental narratives to be a big point of investment for Milwaukee. The Cubs are convincingly winning against good teams, even taking four of the last five games they played against the Dodgers. The Brewers, need I remind you, were just perpetrators of a two-hit shutout against the White Sox. It’s the first week of May, so literally nothing definitive can happen in terms of wins or losses for pretty much any team, but the Brewers can send a message if they put up a convincing fight against the Cubs. Here are some keys as to how they might.

Three Keys To Take Down The Cubs

1. Don’t waste Quintana’s start: Milwaukee’s current WAR leader, veteran lefty José Quintana, is 23 innings into his Brewers tenure—and thriving. After a quietly dominant second half with the Mets last year, Quintana has kept the momentum rolling in 2025. The Brewers scooped him up as a mysteriously overlooked, bargain-bin addition late in the offseason, and so far, the signing looks like a steal. He’ll take the mound against Jameson Taillon, who, unlike many of his surging Cubs teammates, is merely having a good—not great—season. If the Crew can support Quintana with one or two runs, and he keeps looking like he has, they can steal a win here.

2. Don’t waste the Ben Brown start: On the other side of the Quintana excellence coin are Ben Brown’s struggles. The 25-year-old righty had a solid rookie campaign for Chicago last season, but has been struggling massively out of the gates to begin this year. His fastball has lost a mile and a half per hour off of its average, and the result is seeing way less swing-and-miss and way more hard hits. If the Crew avoid the lethal defense lurking in center field, they should use Brown’s start to match the offense the Cubs are likely to show up with. Brown is set to face Quinn Priester to start the season.

3. Continued improvement from the infield: Caleb Durbin may not be turning heads on the national stage as he begins his rookie career, but the 5'7" third baseman is a massive improvement at the hot corner compared to what Oliver Dunn was producing. Isaac Collins, a waiver pick up from the Rockies, has already put up a 0.5 WAR in his 38 plate appearances. Those appearances contain one homer, ten hits and a respectable .781 OPS. Rhys Hoskins probably won’t be the slugger the Crew was hoping he’d recapture when they signed him, but he is actually doing some damage this year compared to last year. Joey Ortiz has taken a massive step back, but there is time to address that thanks to the robust back-up that’s been found in the depth.

Predictions: The Cubs recently had the highest World Series odds, going by one slightly offbeat system, and it’s not hard to see why. They have a lineup that can slug, hit, steal, run the gamut on every offensive cliche you can drum up. They’ve passed the Dodgers barometer test, and looked like they were having fun doing it. There are genuinely some ways I could see the Brewers winning this series, but it doesn’t feel like the most likely outcome. I think it’s two wins to one, in the Cubbies' favor.