The notoriously frugal Pirates have only handed out one nine-figure deal in their history, but most of their biggest contracts have aged surprisingly well.
The Pittsburgh Pirates have never been known for having free-spending habits, handing out just one nine-figure contract in their history. For reference, the Los Angeles Dodgers have seven such players on their 2025 roster alone.
Nevertheless, the team has (reluctantly) stepped up their financial game in recent years, though only on extensions for in-house stars.