Pittsburgh Pirates GM talks leadership, trust, culture — and replacing a legend

Major league baseball front executive Ben Cherington has had some mighty highs and blighty lows in his two decades in the sport. He helped assemble a team (the 2013 Boston Red Sox, where was the general manager) that won a World Series. He also helped assemble teams (like the 2021 and 2022 Pittsburgh Pirates, his current organization) that lost 100 games in one season. 

And after being responsible for hundreds, if not thousands, of decisions, from player contracts to hiring and firing coaches, Cherington says one leadership lesson consistently sticks out: trust. In any decision he makes regarding people, he considers trust first and foremost. He learned that from one of his mentors, longtime baseball executive Mark Shapiro, who, Cherington says, learned it from Hall of Fame baseball executive Pat Gillick. 

It sounds simple, Cherington says, but Gillick, and then Shapiro, would want to know one thing before a final call was made: Could he trust them? “You have to trust them on the field and trust them to do what’s right off the field,” says Cherington, speaking recently at an event in Bradenton, spring training home of the Pirates. The event was hosted by the Manatee Chamber of Commerce.   

While he isn’t batting 1.000 with the trust strategy, Cherington has had plenty of successes. His front office baseball career began about as close to the bottom as possible, when he was named an advance video scout for the Cleveland Indians in 1998. That led to another scouting job, with the Red Sox. A New Hampshire native who grew up a fan of the team, Cherington remained in Boston for 16 seasons, advancing through several roles before being named GM in 2011. In that position, one of the most high-profile front office roles in sports, he replaced Red Sox icon Theo Epstein, who, in 2004, helped deliver the team's first World Series victory since 1918.  

Cherington was named GM of the Pirates in 2019, after a few seasons with the  Toronto Blue Jays. At the Chamber event, Cherington talked about the Pirates’ deep connection to Bradenton, LECOM Park and Pirate City, where the team has held spring training since 1969. After the event I sat down with Cherington to talk about leadership in a hyper-competitive and high-pressure environment.

What are the characteristics that make up a good leader? 

Certainly part of it is being able to set a clear vision for what it is that we are going after and who we want to be. You have to be able to articulate that to the group. Just as importantly, through community and trust-building and support, you have to influence behavior in a positive way. You have to be able to help people move toward improvement, however you measure that. Good leaders do both those things. 

As a leader, how do you develop and maintain a strong and positive corporate or team culture, even among the losses? 

First you need good players. In a baseball environment we are trying to win games on the field, so you need good players. No matter the quality of people you have in the room, if there’s not enough talent on the field and you aren’t winning games, it will be hard to get to the culture you want because you’re going to be getting negative feedback all the time. So at some point you need some positive feedback from the game. 

The second thing is people need to connect to the idea that there's something bigger than the individual that we are going after. It doesn't mean that individual goals can’t be met or aren’t important, too. There’s nothing wrong with individual people aspiring to get the next job or get the next contract, or get a promotion or get paid more. But on top of that there needs to be an idea that we are working toward something that’s bigger than themselves. In baseball, in a way, that’s easy because we have a tangible thing: we are trying to win a championship. 

And the third thing is people in the group have to be interested in adding value to the people next to them. I think the best players I’ve been around had that. They are able to compartmentalize for some of the day; there are certain times of the day where it’s all about them because you are playing (pro) baseball, and it’s really hard and you have to be selfish. You have to make sure you are ready to play and execute. And there are other times where you have to take the time to help other people. I think the best players can do both those things. 

Teams in smaller markets and teams with smaller payrolls, with the Tampa Bay Rays a prime example, often talk about the need to beat the competition in innovation. How do you lead the Pirates to have an innovative mindset?

In a place like Tampa or Pittsburgh, we have this natural constraint that forces us to be resourceful. One of my mentors, (former Indians President and current Blue Jays President) Mark Shapiro, used to say ‘if we just do everything equally as well as the Yankees or Red Sox, then we will finish behind them. Because they will be able to put more resources into the major league payroll and in theory have more talent.’

So in order to win we have to be better in other things than those teams are, which requires innovation. That’s the only way to do it. It’s not a tactic that we are going after but it’s the continuous innovation we are going after. That’s the kind of culture the Rays have established over time. 

Critical to that is retaining and hiring people who want to do that and training them and giving them the resources to do that. There’s all kinds of slogans and words you can use to describe that but we need people with an incredible appetite for learning, have a high level of curiosity and are always seeking the next best thing and a way to do something better. And it doesn’t mean every pursuit we do will turn into something. But we need to pursue a lot to find the stuff that helps us. 

What was it like replacing an iconic leadership figure like Theo Epstein? 

It’s hard. I worked for that group for a long time. On the one hand it was certainly a job I wanted — I had grown up a Red Sox san and aspired for that job. It was part of a lifelong dream. I also thought it was something I had to do, because I wanted to have some continuity and keep our group together moving forward.  

I don’t think I fully realized the weight of it at the time. I definitely remember early on there were times I tried to do the job the way he would, thinking in the back of my mind ‘how would Theo handle this, what would he say in this situation?’ In time I realized you can’t do that. Trying to be someone else is not authentic. Even if I could authentically mimic him, it wasn’t me, it wasn’t the stuff I was good at. I had to fall back on what my strengths were, and that took me a while. 

I was also reminded quickly how big that job is in Boston. There's a lot of stakeholders and a lot of people with a lot of interest in the team and a lot of scrutiny. One of the great things Theo did during the time I worked with him — we didn’t realize it at the time — is he effectively shielded us from all that and allowed us to do the work. He allowed us to be innovators and creators and explote things and be part of this fun environment.I think he shouldered the other stuff. I had to learn how to do that in a way I could handle.