In 1976 Elyahu Ashtor set forth the argument that post-Black Death depopulation in the Levant decreased demand for foods like wheat and barley, leading farmers to increase their cultivation of cotton, flax and mulberries: the three textile crops. As a result, the textile industry saw a boom in the late 14th century. But that boom was a short-lived one, Ashtor argued: the volume and value of goods being exported from the Levant declined in the 15th and 16th centuries. The decline of the textile industry was a contributing factor to the economic decline not only of the Mamluk sultanate but of the whole Islamic Middle East. Ashtor’s theory about the boom and bust of the Levantine textile industry is based upon the ship registries of the Venetian merchants transporting raw cotton to Europe for manufacture, but he provides no numbers for increase or decrease in productivity at the levels of agriculture or manufacture within the Levant. Sources documenting the output of farms and factories are few and far between, and problematic at best. I propose that Geographic Information Systems, or GIS, might be a key to expanding our understanding of the agricultural and industrial productivity of the 14th-15th century Levant, and could provide more reliable estimates for the productivity of cotton cultivation from which we could substantiate Ashtor’s proposed late 14th century textile boom and 15th century bust. This research, still in-progress, considers the real-world application of GIS in the agricultural industry of the 21st century and modifies the methodologies in order to analyse the Medieval Levantine landscape in an attempt to recreate the agricultural conditions of 14th century Syria. This will be done by creating layers of data for soil and irrigation types, elevation and land-cover, rainfall and weather patterns in a 3 dimensional map. Using the innovative data analysis properties of GIS it will become apparent how these agricultural conditions were affected by changing weather patterns, erosion and desertification, demographics, wars and conflict, and market fluctuations, and ultimately will address Ashtor’s assumptions about the growth and contraction of cotton cultivation.