The South Side Masonic Temple sits on the corner of 64th and Green in the heart of Chicago’s Englewood neighborhood. Built in 1921, the seven-story Classical Revival-style building served as a clubhouse for the fraternal order of masons for decades but was abandoned in the 1980s. Since then, the facade has deteriorated as several redevelopment plans have fallen through. This year, for the second time, the temple is on Preservation Chicago’s annual list of Chicago’s most endangered historic buildings. The structure begs the question: when do you give up on trying to preserve a historic building? We discuss when a building should be saved and when it should simply be torn down.