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Ben Cherington shocks baseball again as Pirates bring in another All-Star

Ben Cherington has done it again! In less than a week, the Pirates have brought in another 2025 All-Star player by signing Ryan O’Hearn to a two year deal worth $29M, according to Robert Murray. In less than five days, Cherington has brought in Brandon Lowe, Jake Mangum, and now O’Hearn to rebuild Pittsburgh’s offense.

This is a historic addition for the Pirates, marking the first multi-year, free agent contract since Ivan Nova in 2016. At $14.5M AAV, this is also the most amount of money given to a free agent position player in franchise history.

Everything about this move screams that the Pirates want to win. After a summer of disappointment, this organization has taken a shift in the right direction. This fanbase has been completely rejuvenated and this team suddenly looks like a contending squad.

O’Hearn is coming off a career year, where he generated a 3.0 fWAR with a 127 wRC+ and an .803 OPS. Defensively, he was worth a combined 5 OAA at first base and in the outfield. All around, O’Hearn is an upgrade in every area for the Pirates.

Now that they’ve added a lot to payroll, what’s next? Kazuma Okamoto remains unsigned with his posting window set to close on January 4, and the free-agent market appears stalled as teams wait on Alex Bregman and Bo Bichette. If the Pirates were to shock the league again by signing Okamoto to a multi-year deal, Pittsburgh could suddenly emerge as a legitimate postseason contender.

The offense looks significantly improved, but there’s still room to upgrade. Okamoto may be a long shot, and Eugenio Suárez could be as well, but Yoán Moncada remains a solid option. A reunion with Tommy Pham as a fourth outfielder also makes sense. There are still several viable paths for this team to finalize the roster.

With what the Pirates have now, they have a real shot at a Wild Card spot. A top rotation in baseball with what could be a league average offense. Great work Cherington, baseball in Pittsburgh hasn’t looked this promising in years.

 

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