The Pirates' biggest mistake might not have been passing on Matt Arnold in 2019. It might have been failing to build the kind of organization where someone like him could succeed.
Emma Lingan argues that the Milwaukee Brewers' 2026 World Series title highlights Pittsburgh's deeper organizational failures after passing on Matt Arnold in 2019. Pittsburgh hired Ben Cherington over Arnold as general manager, but the Pirates have yet to make the postseason under his tenure while Milwaukee flourished.
Lingan writes that Milwaukee's sustained success stems from superior infrastructure, scouting, and player development that survived major departures. Consequently, the writer contends Pittsburgh's primary failure is not merely missing out on Arnold, but ownership's inability to build an environment where such an executive could succeed.
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