Street trees are an integral component of urban forests. However, streetscapes are often challenging habitats, which lead to standing dead street trees persisting on these landscapes until their eventual removal. The management of dead street trees is entirely dependent upon human-driven cycles of replacement and removal. However, the fate and persistence of dead trees is not readily apparent during inventory and monitoring studies that capture tree mortality status at a single point in time, or only every few years. In this study, the fate of standing dead street trees were observed based on field remeasurements (2015 and 2021) and Google Street View (GSV) imagery of randomly-distributed plots within Philadelphia, PA. The total percent of standing dead street trees increased from 1.5% (2015) to 2.0% (2021), while the persistence on streetscapes prior to removal decreased from a median of 36-50 months (2015) to 24-38 months (2021). Additionally, the average diameter at breast height (DBH) of dead trees decreased from 15.3–30.4 cm (2015) to ≤7.6 cm (2021). The results demonstrate how current management practices are shifting to remove dead trees on streetscapes faster in order to compensate for the high rate of mortality, particularly in small, young trees. Future studies should investigate management practices that mitigate risk, promote preservation, and encourage stewardship to enable or hinder the removal of dead trees. Further investigation is also needed regarding how the persistence or removal of standing dead street trees alters the structure of urban forests over time.