This thesis is a case study of established media during a period of rapid technological change involving new media. It examines the New Century Network (NCN), a consortium of nine companies that published more than 100 newspapers, including the New York Times and the Washington Post. Formed in 1995, NCN sought to create an online affiliate network linked to a national advertising platform. Reasons typically given for the consortium's demise include the number of participants, primitive technology and the egos of those involved. But previous accounts have largely ignored a significant paradox. Decades before the Internet, newspapers had faced emergent technologies and remained profitable. This thesis argues a defensive posture assumed by newspaper leaders limited their ability to capitalize on potentially groundbreaking ideas that arose out of NCN. These possibilities included a nascent but abandoned effort to use Internet search as a means of maintaining control of newspapers rich content.