Milwaukee Brewers Playoff Scenarios: What’s the Most Favorable Division Series Matchup?

Now that the regular season has concluded, the postseason bracket is finalized. For the first time since 2021, Milwaukee will get to sit out the first round—a hard-earned reward for winning 97 games, more than any other team. Instead of being thrown right back into the fold, their first game won’t be until October 4, when they kick off the Division Series against either the Cubs or the Padres. 

Both teams are formidable potential opponents. Chicago won 92 games and San Diego won 90 this year, placing them comfortably above the 83-win Reds team that snuck into the postseason at the 11th hour. Both teams have exorbitant payrolls that dwarf Milwaukee’s own meager budget, and both have superstar players who could make or break a best-of-five series. 

The Padres were one of the most active teams at the trade deadline, even striking a deal with the Brewers to exchange Nestor Cortes for Brandon Lockridge. While that acquisition ultimately failed to have much of an impact on the team, other major acquisitions like Ramón Laureano, Ryan O’Hearn, Freddy Fermin, and (most of all) Mason Miller helped reshape their team in the second half. 

The addition of Miller, in particular, elevated San Diego’s bullpen to a league of its own. Already stacked with strong arms like Robert Suarez (2.97 ERA), Adrián Morejón (2.08 ERA), and Jeremiah Estrada (35.5% strikeout rate), the Padres had an MLB-leading 3.06 reliever ERA. Unfortunately, Jason Adam, one of their most effective bullpen arms, recently sustained a season-ending rupture of a quadriceps tendon, so they’ll have one fewer weapon to deploy—but it’s still quite a talented array of pitchers.

The Padres may have the advantage in the bullpen, but the Brewers undoubtedly have a more intimidating rotation. Even without Brandon Woodruff in the mix, Freddy Peralta and Quinn Priester should be a strong 1-2 punch, followed by a melange of high-variance but very talented secondary bulk guys. Outside of Nick Pivetta (2.87 ERA), no other Padres starters have been great this year. Randy Vásquez has put up solid numbers, but Dylan Cease, Michael King, and the other arms in the rotation still have things to iron out—and Pivetta will only be available starting in Game 2, should they make it, since he's slated to start Game 1 of the Wild Card Series.

When it comes to the lineup, the Padres seem like they have more threats than the Brewers at first glance, but a closer look reveals that there’s far more parity than meets the eye. Milwaukee has a better team OPS of .735, but that’s the result of everyone chipping in here and there. Other than Andrew Vaughn (who has just 251 total plate appearances for the team), the best hitter on the team by OPS+ is Christian Yelich (121). Despite the Padres having major household names like Fernando Tatis Jr., Manny Machado, and Latin pop sensation Jose Iglesias, the individual numbers are actually pretty even. Here is how the OPS+ figures match up for each team’s top five qualified hitters:

Of course, this leaves out important players who have only been with the team for part of the season, like the aforementioned Vaughn and Laureano, but one can easily see that (beyond name recognition) the Brewers may even have a slightly better lineup. Head-to-head, the Brewers went just 2-4 against the Padres this year, notably losing both series against the team. On the bright side, all but two of the losses were close affairs, which means that they’re likely pretty evenly matched. Besides, the Brewers had little to play for in their matchup during the final week.

When it comes to the Cubs, one might be tempted to say that the Brewers have already proved themselves to be a superior team, after easily claiming their third straight division title. Sure, Milwaukee’s double-digit win streaks and second-half surge are accomplishments worth acknowledging, but that doesn’t mean the Cubs should be underestimated. 

Offensively, Chicago has a slightly better team OPS of .750, but it has more potent individual threat, as well—namely, Michael Busch (148 OPS+) and big offseason pickup Kyle Tucker (144 OPS+). The middle infield duo of Nico Hoerner and Dansby Swanson continues to be one of the best in the business, and despite hitting an offensive wall in August, Pete Crow-Armstrong has begun to turn it around at the plate, while still being one of the best defensive outfielders in the sport. 

Rotation-wise, it’ll be difficult to compete with the Brewers, especially since Cade Horton’s rib fracture will definitely keep him sidelined until at least the NLCS (should the Cubs get there). Matthew Boyd has been a great starter, while Shota Imanaga and Jameson Taillon have been satisfactory, but these three are looking like a clear step down from what the Brewers will be able to muster.

The bullpens are quite close when looking at reliever ERA, but Abner Uribe’s top-notch ERA (1.70) and monstrous workload (74 ⅓ IP) skew the numbers. In reality, guys like Brad Keller (2.07 ERA), Caleb Thielbar (2.64 ERA), Drew Pomeranz (2.17 ERA), and Daniel Palencia (2.91 ERA) have a slight edge over the relievers that Milwaukee will likely deploy, given that Trevor Megill is a bit diminished by injury and Nick Mears appears to be petering out at the end of the year. 

Although the Brewers ended up with a sizable five-game lead in the division, they were actually 6-7 against their I-94 rivals. Just because Milwaukee got the last laugh in the NL Central doesn’t mean the Cubs couldn’t get retribution in a hypothetical Division Series matchup.

Given how these squads match up against the Brewers, I think facing the Padres in the Division Series would give Milwaukee the biggest advantage. The Brewers have a better rotation and lineup, and the Padres have fewer wins and a much lower run differential (+81) than the Cubs (+144). As a fan of baseball, I’d personally love to see a Cubs-Brewers matchup in the playoffs, for the sake of the sport. However, as a fan of the Brewers, watching the Cubs successfully emerge from the Wild Card round could also mean another quick first-round exit for the Crew.