Watching playoff baseball is hard for me, because it often reminds me of how futile the Pirates are in comparison despite being in the same league. This year has been particularly tough though. Not only did the Pirates finally have the talent to be a playoff team and choked it away, we have to watch three small market teams with similar payrolls battle it out in the Championship Series. The one that hurts the most is watching the division rival Brewers curb stomp their way into the World Series. It hurts even more knowing that if the Pirates were smarter, they could’ve been playing in October if they hired the people who run the team from Milwaukee.

The Decision

The Pirates fired Neal Huntington after a disastrous 2019 campaign that became so toxic manager Clint Hurdle wasn’t even going into the clubhouse area where his players were. Huntington had been GM of the Pirates since 2007, and while he had posted four winning seasons and was the most successful leader of the franchise in the 21st century, it was clear that a change in leadership was needed. The Pirates chose to hire the consulting firm Korn Ferry to conduct the general manager search. In the end, the firm had recommended two finalists for the job: Ben Cherington and Matt Arnold. The Pirates ended up going with Cherington, who previously won a World Series in Boston while Arnold stayed with the Brewers. This fateful decision set the Pirates and Brewers on wildly different courses, one trending up and one trending down.

Fast forward to today in 2026, 7 years after Huntington was fired. The Brewers, under promoted GM Matt Arnold, are 100-game winners, swept the juggernaut Dodgers in the NLCS, and are currently one game away from winning the World Series. The Pirates, on the other hand, are just celebrating their first winning season with Cherington at the helm but have yet to even make the playoffs. Since David Stearns was poached by the New York Mets, Arnold has led the Brewers to heights not thought possible. He has won 3 division titles in a row and never won fewer than 93 games in a season, all while on a shoestring budget that doesn’t allow him to go shopping for big stars. He benefitted from inheriting a well-run organization from Stearns, but he has given the blueprint for how small market teams can dominate. It’s impossible not to agonize a little bit as a Pirates fan about what could’ve been.

While the Brewers have won 5 of the 7 NL Central titles since Cherington was hired, the Pirates have been the laughing stock of baseball. Everyone was ready for a rebuild that would take several years, but at this point the Cherington Era is a failure by every metric. The team tanked and drafted 1st overall twice, has never finished higher than 3rd in the division, lost 100 games twice, and has never reached the playoffs. The major accomplishment of the Cherington Pirates has been winning 82 games this year, which was a severe underperformance when considering the talent assembled on the team. Nothing else can encapsulate why the Pirates are where they are better than this hiring choice. It is a microcosm of every rotten aspect of the franchise and why sustained success will never come as long as the people in charge stay the same.

Why Bad Teams Stay Bad

The Pirates continue to lose because Bob Nutting and the people he surrounds himself with are losers. They are not smart baseball people, nor are they even smart business people. Nutting inherited his wealth and businesses from his father, and ever since then, Bob has been a failing businessman. Despite the Pirates appreciating in value from less than 400 million in 2007 to over 1 billion in 2026, Nutting’s net worth hasn’t changed. He simply bought into the one business where it’s impossible not to make millions. He had to sell Seven Springs because it was losing money, and he has overseen the closing of numerous newspapers that came from his dad. If Bob wasn’t born with a silver spoon in his mouth, there is just no way he would’ve achieved the riches and success he has right now. Bad business owners make bad financial decisions and don’t lead companies well, and those issues are all over the Pirates’ organization.

The Pirates have an investment problem. The most glaring problem is the lack of willingness to spend on payroll. Bob has insisted that payroll will only come from ballpark revenue, e.g., the tickets and hot dogs sold at PNC Park. The Pirates clearly have much more money than to spend on the roster, instead that money is pocketed. However, the Brewers also don’t spend much on payroll. If the Pirates want to be the Brewers, they also need developmental investment. Back when Neal Huntington was GM, he had to cut payroll to fund a modern baseball facility for developing prospects and international talent because Bob wouldn’t greenlight the extra funds. This extreme frugalness was occurring during the Pirates’ playoff years of 2013-2015. Bob didn’t have the foresight to see the importance of adding to a successful team’s payroll and developing the next successful team. For years the Pirates were one of the few teams without basic training tools like weighted plates and generally had a reputation for having some of the worst training facilities in the entire league. Not only does this take you out of the running for free agents, but it also means you’re hindering yourself from having low-cost rosters where most of the team is making MLB minimum or arbitration money. Just like how Bob and Company didn’t have the foresight to pass on Cherington, they also don’t have the ability to recognize good investment in the team that will save them millions in the long run.

Ultimately, Bob thinks he can be the Brewers without putting any real thought into why the Brewers are good. He sees the payroll number and assumes that he can achieve the same results. I’m sure Bob is a really nice guy, and his Pirates Charities work is fantastic. I also appreciate his dedication to keeping the Pirates in Pittsburgh. With that said, he should really be realizing that he isn’t fit to own the Pirates, has no clue how to make a winner, and should sell the team. Hiring Ben Cherington wasn’t the worst thing he’s done as owner, but it’s proof that he doesn’t know what he should be looking for to produce a winner for the city of Pittsburgh.

Why Good Teams Stay Good

While the Brewers share many similarities with the Pirates, the organizations couldn’t operate more differently. The Brewers are development geniuses, who are able to pump out MLB-caliber pitchers like it’s an easy task. They made Quinn Priester a good MLB pitcher after 2 other teams failed (including the Pirates). They turned Jacob Misiorowski into a must-watch television prospect instead of a hard-throwing prospect. They even traded for Joel Kuhnel and immediately had him throwing 3 mph faster than what the Athletics did. Not every move works, but they have a philosophy and have become a machine. Their bullpen is Neal Huntington-esque, trading away Devin Williams and Josh Hader and simply replacing them with flamethrowers that provide similar value at a fraction of the price. Their development is so good they can afford to bat Jake Bauers 2nd in the lineup in game 1 of the World Series. They developed Jackson Chourio and Brice Turang into bonafide stars that anchor the lineup and fill in the rest with guys who are annoying to play against. They play incredible defense, run the bases at an elite level, and limit strikeouts. Despite not having many great hitters, their system allows them to fill the holes around their stars with ease. In other words, they make good decisions that are proven to work.

Simply put, the Brewers hire smart people who align with their vision of winning in small market fashion. They invest heavily into analytics and development that have made them one of the best farm systems on a yearly basis. Every single top 100 list now has at least five Brewers in them. They have become a machine that doesn’t need to spend big. The Pirates chose a general manager who won once while spending big, and then signed Pablo Sandoval to an insane deal.

If the Pirates are serious, every single person in the front office should look themselves in the mirror. They need to realize that what they’re doing isn’t working, and if they aren’t willing to change they shouldn’t be in charge. For Bob’s entire tenure, no one seems bothered with a bad process or losing. That creates a culture of losing, and it’s impossible to get that stench off if you aren’t willing to change. It is to Bob and Travis Williams, though I imagine they will continue to be content with being a losing organization.