In this article, I examine how changes in the competitive environment of firms affect matches between chief executive officers (CEOs) and firms. I exploit the 1980 Staggers Rail Act, which drastically deregulated the freight railroad industry, as a source of arguably exogenous variation in the operating environment. Using hand-collected data, I obtain three main findings: first, CEO turnover rates increase; second, relative to utility firms, railroad CEOs have more business education and show broader work experience after deregulation; and third, firm performance leads to CEO turnover only during the regulated period.