First baseman’s 2-year, $29M contract ends franchise’s decade of avoiding free agency commitments

PublishedDecember 24, 2025 7:34 PM EST•UpdatedDecember 24, 2025 7:34 PM EST

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They did it. They finally did it. 

The Pittsburgh Pirates have ended the single most humiliating streak in Major League Baseball. But only by the slimmest, narrowist of margins. And in the most Pirates fashion imaginable. 

Pittsburgh has, to their credit, built an impressive roster of young pitching talent. Paul Skenes followed his National League Rookie of the Year winning season in 2024 by…winning the NL Cy Young in 2025. Skenes is a foundational talent, someone who competitive organizations can build around. He’s added nearly 11 wins above replacement in two seasons, and won’t turn 24 until May 2026. 

Bubba Chandler is one of baseball’s top prospects. Jared Jones had an outstanding start to his career in 2025, before going down with an elbow injury. He’s expected to return at some point in 2026. Mitch Keller provides veteran depth. It’s the makings of a strong rotation. There’s just one problem: they can’t hit. 

If the Pirates were a serious organization, this is where they would sign one of top available free agent bats. Someone like Alex Bregman, Kyle Tucker, or Bo Bichette. There’s just one problem: entering the offseason, they literally had not signed a multi-year free agency contract in a decade. 

Paul Skenes

MILWAUKEE, WISCONSIN – JULY 11: Paul Skenes #30 of the Pittsburgh Pirates throws a pitch in the second inning against the Milwaukee Brewers at American Family Field on July 11, 2024 in Milwaukee, Wisconsin. (Photo by John Fisher/Getty Images)

Pirates End Their Absurd Free Agency Streak

The last multi-year contract the Pirates handed out was to Ivan Nova in 2016. Nova, a journeyman pitcher, got three years and $26 million. Almost too generous, some might say. That generosity was not rewarded, as Nova was frequently injured and mostly ineffective. Apparently, Pirates owner Bob Nutting then decided that winning was simply not worth risking any amount of his profits. So he just…stopped. 

While Pittsburgh has given out extensions to existing Pirates players, they had yet to sign another free agent to a contract longer than one year since Ivan Nova. Until now. 

In an offseason with plenty of available talent, the Pirates signed first baseman Ryan O’Hearn to a 2-year, $29 million contract this week. It’s a Christmas miracle. And one that shows how they’re considering thinking about maybe partially moving towards becoming a serious organization at some point in the next few decades. 

O’Hearn does help the Pirates offense; he had the best offensive season of his career in 2025 with the Baltimore Orioles and San Diego Padres. He hit .281/.366/.437 with 17 home runs, good for a 127 weighted runs created plus, or 27 percent better than league average offensively. 

He’s also nowhere close to Bregman, Bichette or Tucker’s level on offense. And hardly enough to fix the Pittsburgh offense. Even with the addition of Brandon Lowe via trade, they have just three hitters who were significantly above average in their everyday lineup. But hey, at least they’re trying! A little!

It’s a near-certainty that Paul Skenes leaves town as soon as he reaches free agency; the economics of baseball mean that he’ll almost certainly set records for the most expensive contract given to a starting pitcher. Within that window, it’s vital that the Pirates do everything in their power to compete for a championship, or at the very least, playoff appearances. O’Hearn may not be enough to get them there, but it’s a start. 

The thing is, at two years and $29 million, it’s barely one. Let’s hope there’s more.