Abstract: Local Hampton Roads Virginia (USA) folklore has intimated for almost forty years that a Quercus virginiana called “Old Pointe” tree which had been targeted by some City planners to be removed, had a historical connection to the “Emancipation oak” (i.e., a tree that is historically significant in the US because it's the physical location where slavery ended in the US). As we come to the 150 years of the end of the US Civil war this paper shows how modern research can be used to answer a historical ethnological question. The objective of this research was to evaluate the genetic similarity of a Hampton Roads Virginia Live oak (Quercus virginiana Mil. L.) to a historic Q. virginiana called the “Emancipation oak” using random amplified polymorphic DNA. Cluster analysis was used to describe patterns of genetic similarity. Six primers produced 86 bands and had average polymorphisms of 54%. Three Zelkova trees [Zelkova serrata (Thunb.) Makino] were used as an out-group. Analysis using UPGMA dendrogram divided the Quercus and Zelkova species into two distinct groups. A similarity matrix was computed with Jaccard coefficient among the five trees. The cophenetic correlation for the goodness-of-fit of the cluster analysis to the similarity matrix was 0.99. This study successfully demonstrates that RAPD markers can be used in estimating the extent of genetic relatedness of live oaks.