Probate records, documents including wills and estate inventories and auctions, are excellent tools for historical archaeologists who want to better understand the material possessions of past peoples. Probate and archaeological data are particularly amenable to comparison because they both quantify material culture. This thesis compares a sample of 76 16th-century Spanish probate records (both inventories and auctions) compiled in Spanish America to the archaeological assemblages of the 1559-1561 Luna Settlement site and Emanuel Point I (EPI) Shipwreck in Pensacola, Florida excavated by the University of West Florida. The probate records of a variety of Spanish individuals were chosen to reflect the types of people that would have inhabited the site including soldiers, sailors, carpenters, blacksmiths, doctors, artisans, women, etc. This work involves the transcription and translation of historical Spanish documents and the creation of a Probate Inventory Database and an artifact database. The primary goal is to demonstrate the utility of synthesizing material culture data from both the documentary and archaeological records as well as provide an analysis of the similarities and differences between these data sources using the Luna Site and EPI as case studies. An emphasis is made on the idea of "personal property" in 16th-century Spanish America. This project is a model for synthesizing quantitative data from documentary and archaeological sources.