In June of 2021, a 135-year-old church in Auburn, NY - a National Register of Historic Places listed building - was demolished. A church that spanned three centuries of history now takes up space in a landfill. What can we learn from this and how could this have been avoided so we can better retain our history, cultural heritage, environment, and economy for generations? Through a FOIL request, I ascertained the City of Auburn’s actions. I conducted interviews with experts. I investigated the context of the church, historic preservation law, and the potential for deconstruction as a form of preservation. I found the main barriers were the property owner’s inaction and the City’s lack of sufficient policy frameworks to detect problematic structures early on then intervene in a productive manner to avoid wasteful demolitions. Lastly, a lack of interest from a developer to lift a struggling neighborhood sealed its demise.