This article studies the history of Web portals widely used in business-to-business and business-to-consumer Web applications in the late 1990s. Web portals originated from Web search engines in the early 1990s and evolved through Web push technology in mid-1990s to its mature model in the late 1990s. This article also compares Web portals with other popular media, such as radios and televisions, for their audience base and content broadness. As of January 2003, only a few libraries had adopted Web portal technology despite the widespread use of my.yahoo.com-type Web portals in the business sector. The article examines several reasons for the lack of portal development in libraries and concludes with a set of Web portal development guidelines for academic libraries. Some of the pioneer library portals are also discussed, as well as the California State Government, the first government portal to offer customization and financial transactions for individuals and business. This article concludes by probing a more fundamental question about general information storage and retrieval processes. In the last several hundred years, libraries primarily built hierarchical data structures and librarians provided information service without any search engines. In the past ten years, Web business communities have primarily worked on developing fast search engines for information retrieval without paying much attention to data structure. Now with the exponential growth of data on the Web, it is time that librarians and computer engineers work together to improve both search mechanisms and data structures for a more effective and efficient information service. Reprinted by permission of the publisher.