Brewers' NLCS appearance emphasizes one of Pirates' biggest regrets of the modern era

Six years ago, Bob Nutting had a choice to make between two primary candidates to succeed Neal Huntington as general manager of the Pittsburgh Pirates: Matt Arnold of the Milwaukee Brewers, or Ben Cherington of the Toronto Blue Jays.

Needless to say, he made the wrong choice.

The Brewers’ NLCS appearance in 2025 is a painful reminder for the Pirates of what could have been, because it highlights one of the franchise’s biggest modern-era regrets: choosing Cherington over Arnold back in 2019.

When both teams were searching for front-office direction around 2019, the Brewers promoted Arnold internally, trusting the framework David Stearns had built in Milwaukee. The Pirates, meanwhile, hit the reset button with Cherington – a move that led to years of noncompetitive baseball, endless “foundation-building” rhetoric, and an MLB roster still searching for stability six years later.

The Brewers chose smart continuity. The Pirates chose another rebuild. Arnold’s Brewers built forward from a playoff core. Cherington’s Pirates tore everything down and are still trying to crawl out of the hole he dug.

Milwaukee’s rise to the NLCS under Arnold shows what the Pirates keep claiming is impossible: that you can win big with a modest payroll if you’re shrewd, proactive and willing to take calculated risks.
Arnold consistently develops depth through scouting and analytics, trades veterans for controllable MLB-ready talent – not just prospects years away – and finds undervalued players who fit specific roles.

Cherington, by contrast, has leaned on endless “process talk” without translating it to tangible results. His trades (like for Roansy Contreras or Endy Rodríguez) may look smart at first but have yet to anchor a winner. Milwaukee has done more with less, proving Pittsburgh’s stagnation isn’t a market problem; it’s a management problem.

The Brewers under Arnold aren’t just good for a single run; they’re built to sustain competitiveness. Their player development pipeline keeps producing players likeJackson Chourio, Sal Frelick, Joey Ortiz and a parade of capable pitchers.

But where Arnold built a sustainable machine, Cherington built a treadmill. The Pirates, despite all their supposed developmental focus, are still struggling to turn top-100 prospects into consistent Major Leaguers. The contrast is stark: Milwaukee reloads every year, while Pittsburgh keeps promising that the “next wave” will finally fix everything (and it never does).

Brewers' NLCS appearance another reminder that Pirates made wrong choice with Ben Cherington

When Pittsburgh hired Cherington, they could’ve chosen Arnold – a data-driven, progressive executive already thriving in a similar market. Instead, they went with a more conservative, process-heavy approach that feels outdated in today’s analytical era. Now, Arnold’s Brewers are showing exactly what the Pirates hoped Cherington would deliver: a lean, efficient, fearless contender that develops talent and wins at the margins.

The NLCS is proof of concept – and Pittsburgh’s ultimate “what if." Every Brewers playoff win this fall is a flashing reminder of what the Pirates passed on. Arnold took over a small-market team and built a postseason powerhouse, while Cherington took over another small-market team and turned it into a perpetual rebuilding project.

Milwaukee’s NLCS berth is validation of the path the Pirates could have taken – a path rooted in competence, creativity, and trust in modern baseball thinking. Instead, Pittsburgh chose another half-decade of patience and empty promises under Cherington.

The Brewers’ success under Arnold isn’t just a feel-good story for Milwaukee; it’s a mirror showing the Pirates their biggest misstep of the past decade. Pittsburgh had a chance to hire the right architect for a small-market contender. They picked the wrong one, and Milwaukee’s October run is the living, nationally televised proof.