Right now, the New York Yankees and Milwaukee Brewers feel like they’re on opposite ends of a broken bat. Everyone is surprised at how the Yanks are underperforming, having lost eight straight games to their archrivals, Boston. Then, at how the Milwaukee Brewers, the team that’s 20th in payroll in MLB, have managed to come out looking like the best team in MLB!

They are a small market team that cannot even spend like the New York teams, nor LA, nor even their division rival, the Cubs. Not just that, they have traded away big talent over the years, too, like Corbin Burnes, Willy Adames, and even Devin Williams. And they have refused to spend money on big-market stars, and hence, in baseball logic, they should have been as irrelevant as they could be. But here they are in 2025, sitting atop the division.

A big reason for this is the front office. They know how to get the dice rolling to the right number. They play smart and efficient baseball, and they are the “underdog” story other small-market teams want to be. But no matter how good they look, you can’t ignore curses. The team has been great in the regular season but haunted by the ghosts of October.

From the so-called curse of Prince Fielder to the reverse curse that haunts them every postseason, their playoff failures have become baseball folklore by this point. Sure, the New York Mets ended the reverse curse last season, but the truth is that their World Series drought is very much on. And one can’t help but question—will fate be the same this season? Let’s take a closer look at the reasons why they still might be waiting for that championship ring.

1. Bullpen Volatility

When talking about the Milwaukee Brewers, you can’t miss out on their bullpen situation. If you are a baseball fan, you know that making it deep into the postseason requires more than home runs. And for the Brewers, while their bullpen has been effective overall, volatility is looming large, and the recent events are proof of it.

Their recent outing with the San Francisco Giants was an eye-opener. Freddy Peralta gave Milwaukee everything they could have asked for, honestly. Five scoreless innings, six strikeouts, and a chance at winning this game, too. However, once he exited, the game slipped away just as quickly.

Grant Anderson entered in sixth, and defensive miscues opened the floodgates. He got tagged for three unearned runs. Then the Giants tacked on four more when Carlos Rodriguez, their rookie, came in hoping to calm things a little. And just like that, the lead they had was done for, and they finished on the wrong side with a 7-1 score. Ouch indeed! But this is the truth about relief work—one or two mistakes, and the entire game can turn on you. There is no denying that fragility in the bullpen has been an issue, too.

DL Hall, for example, was placed on a 15-day injured list in mid-August because of an oblique strain. Sure, the Brewers are optimistic that he will return in September, but one cannot predict everything. Before the injury, though, he played a crucial role on the roster. After his shaky 2024 season, his 2025 numbers showed an upward trajectory. His ERA was 3.35, and his WHIP went from 1.60 to 1.04. Plus, he was working things out efficiently.

For now, the bullpen, though, remains thin when it comes to the NL heavyweights. And sure, Anderson and Rodriguez are capable, but October is a different animal altogether. One bad inning in a best-of-five or seven can make the difference between a ring and going home.

2. Rotation Depth and Injuries

If there is one thing that can keep the Milwaukee Brewers awake at night leading up to October, it is injuries. Sadly, even they have been riddled with injuries. And for a team like them that doesn’t have a Gerrit Cole or a Spencer Strider to lean on, even a small margin of error can lead to a mess. Everything can change.

Take Christian Yelich as an example. He is the heartbeat of the team, but there is no denying that his body has gone through a lot. Like his 2019 fractured kneecap that ended his season. He has been to multiple ILs due to inflammation and tightness, and his 2024 season was cut off in the summer itself because of his surgery. The good news is that he has fought back every time, but a flare-up in October can be the difference between playoffs and home. And it’s not just him.

The rotation has had its own share of fears. Jacob Misiorowski, for example, was supposed to have a breakout season. And for a while, he was, by blowing away hitters with a 102 mph fastball, and he looked almost untouchable. But that left tibia contusion in early August knocked Misiorowski out for a couple of weeks, and since his return, that spark has been missing. Just 5.1 innings across two starts, eight earned runs, and six walks. That’s not the confidence booster the team needed at this time and place.

There is also Logan Henderson, who was placed on the IL with an elbow inflammation. Now, news is coming that Brandon Woodruff, who was on a long 60-day IL this year, can delay his return, too. Their outfielder Jackson Chourio is also on the injured list. But he did begin his rehab assignment and even went 0 for 3 with a walk in the game. He didn’t end up with explosive numbers, but for the Brewers, that doesn’t matter. They need him right now to get on the field, and they could use him to make the roster feel less fragile.

So injuries, as you see, have made matters tricky for Milwaukee, and if more pieces fall, then the WS dreams might tumble down with them, too.

3. Postseason Experience

Sometimes, even the best of the teams falter post-season. And this is not without reason. The big issue is experience. Sure, talent gets you to a place, but without experiences, things can get messy. And this is where the Brewers come up short—the postseason mileage. Until 2024, for example, they had to tackle one of the strangest curses in baseball, too. Every season, the team that knocked them out of the playoffs went to the World Series.

Think about this—the Yankees back in 1981, the Phillies in 2008, the Cardinals in 2011, the Dodgers in 2018, the Nationals in 2019, and Atlanta in 2021—the result keeps going on.

From 1969 through 2023, they made nine postseason appearances, but they never won. Meanwhile, their opponents reached WS all nine times and even walked away with six championships. This is what is called the reverse curse, and it’s more than their bad luck. In 2024, the curse broke as they lost a wild-card series to the Mets. Also, New York looked great against the Phillies in the NLDS; however, in the NLCS, the Dodgers took care of their business.

For the first time, a team that eliminated the Milwaukee Brewers didn’t make it to the fall. But the tides are far from turning; the experience is a major issue. Because their last serious run they had was in 2018, when they had pushed the Dodgers to seven games in the NLCS. But then, most of the players who were with the team are gone now. This roster is for sure talented, but they lack that veteran energy—because they were traded, right?

The roster is talented but doesn’t seem to have the experience needed to manage the pressure of playoff baseball.

4. Lack of Betting and National Faith

It almost feels unfair—but it is what’s happening. The Milwaukee Brewers put together one of the best seasons so far—almost unbelievable that they would be able to do so. Given that they are the “underdogs of the season.” It’s something even their manager would agree to. However, this underdog aura of theirs might just be seeping into the betting odds and the national faith, too. Because even after playing that great, the sportsbooks continue to tilt towards the powerhouse in MLB, like the Dodgers.

However, there has been a major change. In fact, the Yankees’ and Mets’ betting odds are lower than that. First, the Dodgers are setting pretty at +375, then the Phillies at +600, and then the Brewers at +750. On paper, though, the gap is less about the wins and more about the reputation.

See, the team doesn’t have marquee names, take for example Aaron Judge or even Harper and Mookie Betts. They have players like Issac Collins, Jefferson Quero, and Jackson Chourio, and while they have made their way up, they are not game-changers.

This is the main rub—can a roster that’s full of newbies and rising stars really deliver when it comes to facing the game’s biggest and brightest stars? This is a major question, and it is also a reason why their October storyline is fascinating to others.

5. Possible Offensive Slumps

There is no doubt that the Milwaukee Brewers’ offense has been the surprise element this season. That’s why they’re sitting on top of their division, too. But even then, is there a deep fear that this group can keep hitting when it matters the most? October can humble lineups, and while one is staring down at elite pitching almost every night, slumps don’t take long to creep in. And if you think back to May, there was a point when most of the hitters were underperforming. It looked like the dominance was done with. But then happened the U-turn!

The Brewers went for a 14-game winning streak that ended up just shattering the franchise record. A big reason for their breakout has been guys like Brice Turang. ZiPS had pegged him to be steady but nothing spectacular. But he has added power, all without losing the ability to get to base. Then there is Sal Frelick, who was supposed to be this average hitter. But he turned out to be a real gem and added pop with his contact skills.

Then there is Joey Ortiz, who was hitting .343 in August. However, he got out due to a hamstring strain, and this injury really comes at a lousy time. The Bewers could only hope that he would pick up where he left off. The danger, however, is that emerging hitters of the team are not battle-tested for October just yet. If these players cool off at the wrong time, the offense will kill the chance at rings.

6. Head-to-Head Against Super Teams

The elephant in the room is what happens when October arrives in Milwaukee. Can they hold against the so-called super teams? Teams that are heavyweights, at least in terms of payrolls, deep rotations, benches, and all-stars? The kind of teams where the depth is huge, so that even if a few sit it out, nothing much changes?

On paper, the Milwaukee Brewers have no way to keep up, right? Their payroll ranks 20th in MLB. This is just a fraction of what LA or New York shells out. Moreover, no Shohei Ohtani or Aaron Judge in here. But they have one thing that Pat Murphy, at least, is proud of.

In the skipper’s words, it is their orange life saver! They are the non-flashy players, not players who are stars, but players who play hard and win. And here is the main kicker—Milwaukee has not just survived big-market teams, they have excelled. They swept the Dodgers 6-0 and were unbeaten against Boston and the Phillies. They posted winning records with the Mets, too. So all the bigger teams seem dusted by them. And they had their rising star Jackson Chourio injured, but it didn’t stop them.

Andrew Vaughn and Issac Collins, and even William Contreas played. And this is the thing—everyone contributes. And this is the difference between them and even the big market players. No dependency on a certain “star” player to deliver, or the dominoes fall. For Brewers, it’s about guys grinding together every night. But then, yes, the postseason is another animal, and when the lights are brightest, even the best come under pressure.

Now, whether they wreck or rise above the teams with star power and deep pockets post-season remains to be seen. What’s your guess?