Pittsburgh Pirates' Recent Incompetence in Free Agency Stands Alone Across MLB

Every team except the Pirates has signed at least one free agent to a multi-year contract since the 2022 offseason, while Pittsburgh hasn't done so since December 2016.

Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. / Charles LeClaire-Imagn Images

The Pittsburgh Pirates have come under fire for a lack of spending this winter, but their unwillingness to extend themselves for free agents dates back to well before the start of this offseason.

Burgh Sports United's Jason Shetler took to social media on Friday to note that the last time the Pirates signed a free agent to a multi-year contract was all the way back in December 2016, when they inked starting pitcher Iván Nova to a three-year deal worth $26 million.

It has been 2,965 days since Nova put pen to paper in Pittsburgh.

December of 2016 was the last time the #Pirates signed a free agent, to a multi-year deal (Ivan Nova). Let me repeat that again - December of 2016. How doesn’t MLB look into this? For a team to go that long, with a multi-year commitment, is complete lunacy.

— Jason Shetler (@Jason_Shetler) February 7, 2025

Looking elsewhere across the league, the Pirates stand alone in that regard.

All but five teams have signed at least one free agent to a multi-year contract between the last two offseasons alone. The Cleveland Guardians, Minnesota Twins and Miami Marlins did so most recently ahead of the 2023 campaign, while the Colorado Rockies did so coming out of the MLB lockout in March 2022.

Go back another five years and three months, and you have the last instance of the Pirates' front office issuing a contract longer than one year to a free agent.

Owner Bob Nutting doesn't seem to want to sell the team anytime soon, much to fans' chagrin, while general manager Ben Cherington hasn't made many significant external additions since taking over in November 2019. Although Pittsburgh has awarded extensions to Ke'Bryan Hayes, Bryan Reynolds and Mitch Keller, those deals were struck far away from the open market.

Extending Oneil Cruz, Spencer Horwitz and especially Paul Skenes could prove difficult if the Pirates' front office continues to avoid making long-term commitments, so their hesitance in free agency may come back to bite them in a destructive way.

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