Much of the original Interstate infrastructure built in the 1950s and 1960s in the United States is approaching or has already reached the end of its useful life, and now requires large investments for rehabilitation. At the same time the freeway revolt has evolved into a more widespread movement, underlined by values such as sustainability. The vigorous debate about the future of urban highways and mobility continues with the development of a fairly recent phenomenon: urban freeway removal. This paper works toward a theory of highway removal by examining three different cases in which urban freeway removal was a seriously considered option-two in which the freeway was removed and replaced with a lower-capacity at-grade boulevard and one in which the freeway ultimately was not removed. The analysis suggests that freeway removal will take place only when (a) the freeway's condition raises concerns about its integrity and safety; (b) a window of opportunity exists, some event that enables a freeway removal alternative to gain serious consideration; (c) the value of mobility is lower than other objectives such as economic development; and (d) those in power value other benefits more than they value the benefits associated with freeway infrastructure.