Pirates passed on Matt Arnold in 2019, but Brewers' World Series win exposes a much bigger problem

In November 2019, the Pittsburgh Pirates were searching for a general manager who could transform their struggling organization into a sustainable small-market contender.

One of their finalists was Matt Arnold, an executive who had spent years working for two organizations that had already figured out how to do exactly that: the Tampa Bay Rays and Milwaukee Brewers.

Pittsburgh ultimately hired Ben Cherington instead.

Seven years later, Arnold is celebrating Milwaukee's first World Series championship, while the Pirates are still waiting for their first postseason appearance of Cherington's tenure.

It's the kind of decision that will inevitably leave Pirates fans wondering what might have been. But the bigger question isn't whether Pittsburgh hired the wrong general manager. It's whether the organization ever truly understood what made teams like Milwaukee successful in the first place.

Pirates' missed opportunity with Matt Arnold reveals a deeper organizational problem

At the time when the Pirates hired him, Cherington was an understandable choice. He had won a World Series as Boston's general manager in 2013 and built a reputation for scouting and player development.

But Arnold brought something arguably more relevant to Pittsburgh's circumstances: extensive experience operating within the financial limitations of small-market baseball.

When the Pirates introduced Cherington, team president Travis Williams acknowledged that other small-market organizations had already figured out how to compete. Seven years later, Milwaukee has done it. Pittsburgh still hasn't.

The Brewers won 103 games in 2026 before capturing their first championship. They've reached the postseason eight times in nine seasons, establishing themselves as one of baseball's most consistently successful franchises.

Meanwhile, Pittsburgh's long-awaited rebuild finally produced an 82-80 record in 2026, its first winning season since 2018. That's progress, but it's a considerably lower standard than the one Milwaukee has established.

Still, attributing that entire difference to one executive would miss the most important lesson. Milwaukee's success didn't begin with Arnold, and it certainly doesn't depend entirely on him. David Stearns helped establish the Brewers' competitive foundation, while Craig Counsell provided stability in the dugout. When both departed, Milwaukee promoted Arnold and Pat Murphy from within.

Instead of collapsing under the weight of those departures, the Brewers continued winning. That kind of organizational continuity doesn't happen by accident. Milwaukee has invested in scouting, player development and front-office infrastructure that allows the franchise to identify talent, replace departing contributors and remain competitive without repeatedly starting over.

Arnold inherited a successful operation, helped strengthen it and ultimately guided it to a championship. The fact that the Brewers could withstand significant leadership turnover speaks to the strength of the entire organization.

That raises an uncomfortable hypothetical for Pittsburgh. Even if the Pirates had hired Arnold in 2019, would he have experienced anything resembling the same success? Would he have received the same organizational support, resources and flexibility? Would Pittsburgh's ownership have committed to building the infrastructure necessary to sustain a winner?

There's no way to know, and that's precisely why the Pirates' problem extends beyond Cherington.

The front office deserves scrutiny for a rebuild that has taken seven seasons to produce a winning record, but ownership ultimately bears responsibility for creating an environment where sustained success is possible.

Milwaukee has demonstrated that small-market limitations don't have to prevent an organization from developing a championship-caliber operation, and the Pirates have spent years talking about following that blueprint. Back in 2019, they had an opportunity to hire an executive who had already helped put it into practice. They chose another direction, and seven years later, the results speak for themselves.

Perhaps Arnold wouldn't have succeeded in Pittsburgh. Perhaps the obstacles that have plagued the organization for decades would have limited him, too. But that possibility might be the most damning part of this entire comparison.

The Pirates' biggest mistake might not have been passing on Matt Arnold. It might have been failing to build the kind of organization where someone like him could succeed.

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