A growing number of cities are choosing to remove parts of their urban freeway network to make room for alternative land uses. This study examines the history of two freeway spurs in Milwaukee—the Park East Freeway and Interstate 794—which were both targeted for demolition. Park East was demolished in 2002, but Interstate 794, which was considered for partial demolition on two separate occasions, was eventually rebuilt. This study asks what the cases of Park East and I-794 can tell us about the attributes of a successful freeway teardown project. This study traces the history of both freeways from the 1950s to the present, drawing on a mix of newspaper coverage, archival sources, planning documents, and relevant scholarly studies. This thesis makes two arguments. First, it argues that the cases of Park East and I-794 support the idea that freeway removal efforts may need: (1) An adequate window of opportunity; (2) a strong advocate for the teardown option; (3) strong business support, and; (4) reasonable assurances from teardown proponents that the removal option will “do no harm.” Second, it argues that the I-794 outcome can be partly explained by a major state investment in the freeway in the 1990s