Milwaukee’s Masterclass: The tale of two front offices
Kamil Krzaczynski - USA Today Sports

Milwaukee’s Masterclass: The tale of two front offices


Ariana Pensy Ariana Pensy  ·  Correspondent ·  

As game three of the NLDS at Wrigley awaits a Cubs team that trails its NL Central rival 0-2 in a five-game series, many of the talking heads have shifted their focus to some of the shortcomings of this roster in 2025.

Any members of the organization would tell you there is a game to win and a series to extend before you zoom out and look at the big picture, but it's hard to ignore the gap in franchises between the Brewers and the Cubs.

Now, before delving deeper into that gap, it’s hard to classify 2025 as a failure even if the Cubs are swept in the NLDS. The ball club won 90 games for the first time since 2018, which coincidentally marks the last full season they reached the postseason. The Cubs had a trio of 30 home run hitters, the first time any Cub has posted that mark since 2019. For the 7th time in franchise history, the Cubs are likely to boast the rookie of the year in Cade Horton. Not to mention, they clinched a playoff series at home to the delight of the Wrigley Faithful.

That being said, it’s impossible to ignore the glaring disappointment that would come from a series loss. The Cubs noticed from a far how well Milwaukee ran business — consistently doing more with less. In fact, the Cubs were so impressed that they poached Craig Counsell as manager and offered him the most money in the league… only to watch Milwaukee win the division in back-to-back seasons without Counsell at the helm. Since 2018, the Cubs have watched the Brewers have far more success despite spending far less — and turns out it wasn’t only the manager who was responsible. This, of course, while the Brewers are operating a roster that costs more than 80 million dollars per year, less than Chicago’s.

Yet, in October, the Cubs’ roster, worth nearly $200 million, does not resemble the roster of a big market team. The Brewers scored as many runs in game 1 as the Cubs have scored in all five playoff games they’ve played this postseason combined. Plus, they have a handful of relievers that can throw over 100 miles per hour on their pitching staff, which includes some of the best starters in the NL.

Unfortunately, this is a familiar sight for the Cubs in October. In fact, in Chicago’s last 18 playoff games (dating back to 2017) they are averaging less than 3 runs per game, and their .176 team average is the worst in baseball history by any team across an 18 game sample size.

2016 was a miraculous year that can never be taken away from the Cubs or their fans. However, as more years pass, 2016 continues to appear as a massive outlier. The club’s competitive seasons have often featured offensive slumps in the postseason or September collapses, which cause the team to miss the playoffs altogether.

Even as the manager, hitting coach, and lineup itself change, the results unfortunately have not. Meanwhile, Milwaukee is running circles around the organization. The Brewers’ success has become so deafening that many Cubs fans have begun to speculate that they must be stealing signs. The truth is, they deserve credit for their scouting and development, as for the better part of a decade, they have churned out a team whose record is significantly better than that of the big-market Cubs.

Look no further than Quinn Priester. In three big league seasons before coming to Milwaukee, Priester had a career ERA north of six. In 2025, the right-hander has a 3.32 ERA and a 13-2 record, with a career high of 157 innings and 132 strikeouts. The Brewers had a stretch this season where they won 19 consecutive games started by the 25-year-old. Andrew Vaughn, Jose Quintana, and Trevor MeGill are among those success stories — meanwhile, they boast a top-5 farm system in baseball.

Now the Cubs have time to right the ship in this series and keep their season alive. But, I hope that a deeper playoff run wouldn’t cloud the mirror that the organization needs to look in.

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