The direct physical loss from a tornado is one possible factor in considering resilience goals for a community. Estimating such loss has historically been done either through analysis of empirical data from historical events meant to then match future hypothetical events or through a cost analysis based on a building’s damage state. These approaches provide a solid baseline for estimating loss from wind events; however, gathering data from historical events may assume all locations are the same, while analyses based solely on the building damage state may not include a building’s contents. This study builds on work previously established in determining loss from building damage state fragilities, by including a loss to the building’s interior (including contents) based on FEMA’s HAZUS equations. The approach laid out in this paper is then validated, showing what is deemed an acceptable level of accuracy, using the May 22, 2011 Joplin tornado that devastated the local community. Once validated, the same tornado path is relocated in different directions, ultimately crossing most of city of Joplin in four additional hypothetical scenarios. The results of both hindcasting the 2011 Joplin Tornado and its hypothetical track variations show commercial (non-residential) type buildings as key in contributing to the direct physical loss of a wind event. Ultimately, this provides decision makers with a point of consideration when evaluating their community’s resilience goals.