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Previous bioarchaeological analysis of postmortem tooth loss (PMTL) has failed to recognize the potential influence of diseased dental tissue on tooth retention after death. Because tooth loss from a traditional taphonomy prospective is treated simply as missing data, demographic studies are potentially influenced by underestimations of disease prevalence. To investigate the association of tooth loss and dental disease, tissue health data was collected on a sample of teeth from 771 individuals. By analyzing the health of the bone and dental tissues immediately surrounding empty alveolar sockets suggestive of PMTL, trends in the presence of diseased tissue and retention of a tooth emerged. When compared to teeth retained after death, PMTL sockets were 15.3% less likely to retain neighboring teeth and 21.5% less likely to have neighboring teeth that showed no signs of carious lesions or abscesses. The results suggest that the traditional explanation of susceptibility to damage because of the exposure and morphology of single-rooted, anterior teeth does not sufficiently explain the causes of PMTL. Rather, it would be more accurate to consider PMTL as an advanced symptom of dental disease when interpreting missing teeth in the bioarchaeological record.