Loading
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.
Subscribe today. Cancel anytime.
Your free article limit has been reached this month.
Subscribe now for unlimited digital access to our award-winning business news.
Join thousands of executives who rely on us for insights spanning Tampa Bay to Naples.
