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Ryan O'Hearn Discusses Building Pirates Winning Culture
Sep 27, 2025; San Diego, California, USA; San Diego Padres first baseman Ryan O'Hearn (32) gestures after hitting a double during the second inning against the Arizona Diamondbacks at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images Denis Poroy-Imagn Images

PITTSBURGH — The Pittsburgh Pirates have spent this offseason looking for ways that will improve their roster and the addition of Ryan O'Hearn is one of those moves they hope will do that.

O'Hearn joined the Pirates on a two-year, $29 million deal officially on Jan. 8, the marquee free agent signing for the franchise this offseason.

The slugger, who can play many different positions, is the first free agent multi-year signing for the Pirates since right-handed starting pitcher Iván Nova for three years, $27 million on Dec. 27, 2016. He is also the first free agent position player multi-year signing for Pittsburgh since outfielder John Jaso for two years, $8 million on Dec. 23, 2015.

O'Hearn now has a big role for the Pirates in 2026, helping end the agony for the fanbase and delivering winning baseball.

Ryan O'Hearn Discusses Building Winning Baseball Culture

It wasn't long ago that O'Hearn found himself out of favor with his first ball club and at a difficult point in his career.

O'Hearn spent his first five MLB seasons with the Kansas City Royals, but never established himself as a solid bat, hitting .219 and possessing a .683 OPS during that time.

The Royals designated him for assignment at the end of 2022 and then traded him to the Baltimore Orioles.

O'Hearn eventually established himself with Baltimore, having a breakout season, slashing .289/.322/.480 for an OPS of .801 and putting himself on the right path towards success in baseball, earning an All-Star nod in 2025.

"I think it's really a combination of a lot of things," O'Hearn said on his improvement with the Orioles. "I feel like I've taken something from every hitting coach I've ever worked with and I've worked with some really great hitting coaches. And when I got to Baltimore for whatever reason it kind of clicked.

"You know how it is in this game. When you're struggling you can just kind of feel defeated because it's every day. But it's the same thing when you start to have success, you start to realize, 'Hey, I'm a guy.' I think that happened for me in 2023..."

His success as a hitter also coincided with the Orioles becoming one of the best teams in the major leagues.

The Orioles saw an 18-win improvement from 2022 to 2023 and finished with 101 wins, the second-most wins in baseball, behind the 104-58 Atlanta Braves.

Baltimore also made it back to the playoffs the following season at 91-71 and after they traded him to the San Diego Padres at the 2025 deadline, he still made the postseason with them.

O'Hearn looked at how that 2023 team came together in Baltimore as a big reason for their success.

They took their underdog mentality coming into the season and then kept a good mindset the whole season, which helped them deal with losses and disappointments throughout, while also enjoying success when they earned it.

“That’s a great question. It happens organically. In 2023, when I got to the team, the expectations weren’t – we expected to be, like, good but nobody thought that team was going to win 101 games in April. It just happened. Guys were committed to having fun, enjoying each other – you’ve got to have fun.

"The team has to enjoy being around each other, doing things together. You have to enjoy showing up to work. The attitude when it’s time to get after it, you get serious and you get after it. You celebrate wins. When you lose, you wear it and you move on. There’s too many games in the season to get down on yourself. Stuff happens every day in this game. It’s a crazy game. Just having each other’s back, picking each other up and keep this thing moving one day at a time. That’s how you go about it.”

Pittsburgh hasn't made the postseason since 2015, nor had a season above .500 since 2018, both the second-longest streaks in baseball.

O'Hearn has that experience of winning with a small market club and the Pirates will need his expertise and leadership, as they try and field a competitive outfit in 2026.

This article first appeared on Pittsburgh Pirates on SI and was syndicated with permission.

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