Pittsburgh Pirates: Assessing the Best Free Agent Signings of the Past 25 Years

Which GM has the best track record of attracting talent to Pittsburgh?

Milwaukee Brewers v Pittsburgh Pirates
Milwaukee Brewers v Pittsburgh Pirates / Joe Sargent/GettyImages
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No. 1 The Ben Cherington Era (Nov. 2019 - present)

Jose Quintana (Nov. 2021, 1 year, $2 million)

Cherington’s reuses this script every offseason: a mid-career starter signed to eat innings and mentor young pitchers. Compared to the more recent contracts with Rich Hill and Martin Perez, though, the Quintana deal was a steal.

Quintana turned in his best performances since an All-Star campaign with the White Sox in 2016. He ranked in the top 10 in ERA, games started, and FIP, and he led MLB in home runs allowed per nine innings. Quintana’s four-seamer had a resurgence and ranked as the 20th most effective pitch in the Majors based on run value.

The cherry (or Cherington) on top of this signing, though, was its yield. With the Pirates sitting at 47-58 and the Trade Deadline approaching, Pittsburgh flipped Quintana and reliever Chris Stratton to St. Louis for two highly regarded, young, controllable players: Johan Oviedo and Malcolm Nunez. 

Before undergoing Tommy John surgery in late 2023, Oviedo, who won’t hit free agency until 2028, racked up 2.9 WAR and displayed one of the most devastating sliders in the game. Nunez rose quickly through the farm system, ending 2023 with Triple-A Indianapolis. He currently ranks as the Pirates’ No. 22 prospect and will likely make his Major League debut in 2024. Quintana, meanwhile, signed a $13 million, two-year deal with the Mets before 2023 and missed half of that season due to injury.