Brewers Success is an Embarrassment for Pirates

Cherington ended up winning the job, and Arnold eventually earned promotion to Brewers general manager, as the franchises went in different directions.

The Pirates have had just one winning season under Cherington, which came this season and on the very last day, finishing 82-80.

Milwaukee has made the playoffs six of the past seven seasons under Arnold, including five National League Central Division Titles and winning the past four.

Arnold's background was scouting, and he helped the Tampa Bay Rays build a strong pitching foundation, one that has still played a big part in the franchise's success today.

The Brewers have a fantastic pitching staff, and Arnold has also done well when having to move players ahead of them, hitting free agency and commanding a big contract.

He traded right-handed starting pitcher Freddy Peralta to the New York Mets this past offseason for prospects, infielder Jett Williams and Brandon Sproat, while dealing right-handed closer Devin Williams to the New York Yankees for left-handed pitcher Nestor Cortes and Caleb Durbin ahead of 2025.

Arnold then traded Durbin, plus two prospects, to the Boston Red Sox for left-handed pitchers Kyle Harrison and Shane Drohan and infielder David Hamilton before this season.

Harrison and Drohan have had big roles on the Brewers' pitching staff, and Hamilton became the starting third baseman, putting up solid numbers in Durbin's replacement.

Peralta struggled with the Mets, and they traded him to the Rays at the deadline, where he's been better, while Devin Williams lost his closer role with the Yankees in 2025 and wasn't great with the Mets in 2026.

The Brewers have also developed their young prospects into stars, while prioritizing their best talents: designated hitter Christian Yelich, second baseman Caleb Durbin, left fielder Jackson Chourio and first baseman Jake Bauers.

Milwaukee is an excellent pitching team, with NL Cy Young hopeful in Jacob Misiorowski leading a rotation that has had its injury issues.

The bullpen is where the Brewers have excelled, with the likes of Aaron Ashby, closer Trevor Megill, Abner Uribe, Chad Patrick and DL Hall dominating opposing hitters late in games.

Arnold has built the Brewers into a team that could not just win the World Series this season, but be ready to do so every year going forward for the foreseeable future.

Why the Pirates Haven't Had the Same Success

Cherington led the Pirates on a rebuild at the start of the decade, which has resulted in little success for the Pirates.

The Pirates finished with the worst record in 2020, 19-41, back-to-back 100-loss seasons in 2021 and 2022, then 76-86 finishes in 2023 and 2024, where they actually had good starts to the season.

That 2024 season was even more important, as the Pirates were above .500 at the trade deadline, before an 8-19 August sent their season into disarray.

Cherington and the Pirates' front office, instead of bolstering the roster by going after players who could make it better, settled on veterans in outfielder Tommy Pham, infielder Adam Frazier and left-handed starting pitcher Andrew Heaney.

The Pirates, as a result, were awful for most of 2025, starting 12-26, which led to the dismissal of manager Derek Shelton and a 71-91 finish, the fifth-worst record in baseball and last in the NL Central.

Changes were made last offseason, big additions in second baseman Brandon Lowe by trade and Ryan O'Hearn in free agency, both of whom played big roles for the Pirates in 2026.

The Priates seem to be playing "catch up" after every season, constantly trying to fix mistakes, rather than building on something that will ensure a winning team for the future.

Pittsburgh's additions of Lowe and O'Hearn helped turn their lineup from the worst into one of the better in baseball, but it also resulted in neglecting the bullpen.

The Pirates bullpen blew too many important games, and another slump. 7-16 from late July to mid-August was too much for them to overcome.

Pittsburgh addressed the bullpen at the trade deadline, and, likely, they'll do so again this offseason, but there will likely be another area they're missing on either improving or bolstering.

Pirates Fans Feel General Apathy Towards Team

This was the second season I've covered the Pirates, with this past season much better than 2025, but still the same end result: no postseason baseball.

Pirates fans, even the most hopeful ones, likely have a hard time seeing their franchise ever becoming a perennial winner like the Brewers are.

Both teams are similar: small-market ballclubs that need to make strong front office decisions from the MLB Draft, free agency and the trade market to maximize talent.

Payroll is also close, with the Brewers' higher than the Pirates', $146 million to $106 million, but far from the Dodgers' $339 million.

The Pirates haven't done anything like the Brewers in the past few decades, last winning the World Series in 1979 and only making the postseason six times since.

Milwaukee has been far more successful, with 10 postseason appearances since 2008 and a chance to win its first World Series.

The difference was felt with Pirates fans at PNC Park and Brewers fans at American Family Field this season, and I noticed it when walking around the concourses.

Pirates fans, even if they were optimistic, were still cautious about whether they fully believed their team could finally make the postseason.

Brewers fans expect a great product, and they get one, making it easy to come to games and root for the home team.

It's no surprise to see the differences in attendance, with the Brewers posting the 11th-highest average (34,431) and the Pirates posting the fifth-lowest (21,064).

Winning baseball takes time to build and the Brewers support shows that, while losing baseball is emblematic in attendance from Pirates fans.

Can Pirates Turn Things Around?

The Pirates have a big season ahead of them in 2027, one they are confident they can end their postseason drought, last making it in 2015.

It's the second-longest postseason absence in baseball, with only the Los Angeles Angels longer (2014), and one that the Pirates need to break before aiming to become the next "Brewers".

The Pirates have a strong, young rotation, a bullpen that should improve with more additions and a lineup that can do some serious damage.

It's not the biggest window for the Pirates, as many of their best players are entering arbitration, but as a small-market team, they must take advantage.

Cherington deserves criticism for his tenure with the Pirates, but he has still made them a much better team through the draft, particularly with starting pitcher Paul Skenes (first overall in 2023) and shortstop Konnor Griffin (ninth overall in 2024).

The Pirates have a young team wanting to buck the losing trend and a hometown manager, Don Kelly, who would love nothing more than to do that.

It's been incredibly disappointing for Pirates fans over the last few decades, even embarrassing watching a small-market team like the Brewers have the success they've had.

A postseason appearance in 2027 is a must, and if the Pirates can achieve that, they can start building the foundation for a winning ball club.