Pirates Break Nine-Year Drought With Major Free Agent Deal
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In a move that reshapes both their payroll and competitive expectations, the Pittsburgh Pirates have signed first baseman Ryan O'Hearn to a two-year, $29 million contract, marking the largest annual salary commitment to a free agent in the franchise's history.
The Pittsburgh Pirates are continuing to make definitive statements about their intentions for the 2026 season, reportedly agreeing to terms with free-agent first baseman Ryan O'Hearn on a two-year, $29 million contract.
The deal, which includes $500,000 in performance bonuses available each season, represents the first multi-year contract the franchise has given to a free agent since pitcher Ivan Nova in December 2016. O'Hearn's contract was reportedly signed on December 23rd, while Nova's was signed on December 22, making this the Pirates' biggest free agent move in almost exactly nine years to the day.
A splash for the Pirates: Free-agent first baseman Ryan O’Hearn and the Pittsburgh Pirates are in agreement on a two-year, $29 million contract, according to sources familiar with the deal. It includes $500K in performance bonuses in each season.
— Robert Murray (@ByRobertMurray) December 23, 2025
The signing directly follows through on General Manager Ben Cherington's stated goal this offseason to increase spending and bolster the team's offense. It comes just days after the team executed a three-team trade to acquire second baseman Brandon Lowe from the Tampa Bay Rays, further demonstrating an aggressive approach to upgrading the lineup.
A New Financial Era in Pittsburgh?
For years, the Pirates' activity in free agency has been characterized by modest, short-term commitments. The O'Hearn deal shatters that pattern in both total value and, more notably, average annual value. There are three major takeaways from the signing:
- At $14.5 million per year, O'Hearn's contract carries the highest Annual Average Value (AAV) the Pirates have ever given a free agent.
- This breaks a near-decade-long drought of multi-year free agent deals. The last such contract was Ivan Nova's three-year, $26 million agreement in 2016. The last position player to receive one was John Jaso on a two-year deal in December 2015.
- The move aligns with management's pledge to add roughly $30-40 million to the 2026 payroll. Following the acquisition of Gregory Soto, owed $7.5 million next season, as well as Brandon Lowe, who is owed $11.5 million in 2026, the Pirates' spending this offseason is demonstrating a tangible shift in philosophy.
Ryan O'Hearn: A Late-Blooming Bat
O'Hearn, 32, arrives in Pittsburgh as a player who has revitalized his career in recent seasons. After spending his first five years with the Kansas City Royals, where he struggled for consistency, a trade to the Baltimore Orioles before the 2023 season sparked a dramatic turnaround.
The left-handed hitter earned his first career All-Star selection in 2025 as a member of the Orioles before being traded to the San Diego Padres at the July deadline. Last season, split between Baltimore and San Diego, he slashed .281/.366/.437 with 17 home runs and 63 RBI, posting an OPS+ of 125, indicating his bat was 25% more productive than the league average hitter.
His primary value lies in his steady, above-average offensive production as a left-handed bat. Over the past three seasons with the Orioles and Padres, he has been a reliable run producer, adept at getting on base and providing occasional power. Defensively, he provides experience at first base and has also seen time in the corner outfield positions.
Building Around a Pitching Foundation
The Pirates' offseason strategy appears focused on capitalizing on a promising young pitching staff, anchored by 2025 National League Cy Young Award winner Paul Skenes. The logic is clear: by adding proven offensive pieces like Lowe and now O'Hearn, the team aims to convert strong pitching performances into more victories.
General Manager Ben Cherington acknowledged this approach earlier this offseason, stating, "The odds increase a little bit each offseason with the combination of players seeing the strength of our pitching and the opportunity to win with that pitching foundation, and a little bit more flexibility".
The back-to-back acquisitions address two clear areas of need. Brandon Lowe brings proven power from the left side of the infield, while O'Hearn provides a high-contact, on-base presence who can slot into the middle of the lineup. For a Pirates team that finished 2025 with a 71-91 record — their seventh consecutive losing season — adding established major league talent is a direct response to years of offensive struggles.
The O'Hearn signing is more than a simple player acquisition; it is a symbolic break from a long-standing organizational pattern. The Pirates have historically preferred to extend their own players — like Bryan Reynolds, Ke'Bryan Hayes, and Mitch Keller — rather than pursue premium outside talent in free agency.
By committing nearly $30 million to a free agent, the Pirates' front office is signaling to a weary fanbase and the rest of the league that the period of extreme financial restraint may be ending. Whether this marks the beginning of a sustained competitive push or a short-term anomaly will be revealed in the seasons to come. For now, the message from Pittsburgh is clear: after nearly a decade, they are officially back in the free-agent market.
Ethan Merrill is from Grand Rapids, MI, and brings with him a diverse background of experiences. After graduating from Michigan State University with a degree in journalism, he worked with the Arizona Diamondbacks for three seasons before settling in the Pittsburgh area in 2020. With a passion for sports and a growing connection to his community, Ethan brings a fresh perspective to covering the Pittsburgh Pirates.