Here is a short piece that describes the myth behind the devil at the crossroads. It explains the myth much better than I could personally.
The crossroads is a place loaded with superstitions and stories. Back in the days before the automobile and paved highways, people traveled dirt roads through the wilderness and bayous either on horseback or by foot. The pace of the journey was generally slow and often caused the mind to wander in the trees and shrubs. In a way travelers were much more vulnerable. They did not have the safety of their cars or road side phones to call for help. And as darkness fell, I'm sure that all of the superstitions and stories of evil devoured their consciousness.
Many countries such as the European countries, India, Greece and Japan, as well as people such as the American Indians, subscribed to the superstitions and folk tales of the crossroads. At these intersections, demons, evil spirits, ghosts, Kobolds and fairies were found. It is a burial place for suicides and murderers and a dump heap for parricides. The crossroads is a rendezvous for witches who use this place for Sabbat rituals. Sacrifices were offered to the gods to protect humans from the evil which lurked here.
Legba is a trickster deity and god of entrances and crossroads. He is part of the belief systems of blacks of Dutch Guina, Brazil, Trinidad, Cuba and the voodoo cult of Haiti and New Orleans. In the new world, Legba goes about in tatters and he functions in cult rituals "to open the way" for the gods to possess their devotees. For this reason his songs are sung first at all rites. In the new world syncretism he is often equated with the devil. With this information, we can assume that when Robert Johnson made his claim of meeting the devil, he was referring to Legba.
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