Since the early 1970s, as shipping has undergone a period of structural change, Swedish shipping has rapidly declined from a position of global importance. The Swedish-controlled fleet has dwindled, and the structure of the industry itself has changed. This article explores the influence of shipping markets, shipping regulations, company strategies, maritime know-how, and financial resources on the development of Swedish shipping from 1970 to 2010. A comparison is made between, on the one hand, the direction taken by two failing companies and, on the other, the courses followed by two companies that managed to grow despite difficult conditions. On a broader level, the article traces the development of expertise in a declining industry.