The Pirates hired Ben Cherington seven years ago. Another name in that GM search now sits atop one of baseball’s most successful small-market organizations.

With Matt Arnold and Milwaukee providing an unavoidable comparison, DiNardo and Tyler revisit Pittsburgh’s decision and a much bigger question: why has one organization built sustainable success while the Pirates continue waiting for their window to truly open?

They also dig into Sean Buchanan’s hiring and what it could mean for Pittsburgh’s pitching development.