Recognizable by their cunning exploits and gray morality, tricksters can be found in mythology, folklore, and religions throughout the world. Two tricksters were familiar to the Yoruba people in West Africa, Ajapa and Eshu, and their stories and abilities provide insight to the functions fulfilled by trickster characters. Upon the introduction of Regla de Ocha (or Santeria) to Cuba following the transatlantic slave trade, a new figure emerges, known for his tricks and adaptability. Due to the West African influence in Santeria religious practices, the original roles and traits of Eshu and Ajapa are analyzed for comparison, but Eleggua, the Santeria trickster, has become his own entity. Through ethnographic observations, personal conversations, and a collection of various sources and manuals, this project explores Eleggua and the trickster presence in Cuba. Although his role as a trickster has changed throughout the past few centuries, Eleggua and the trickster identity persists in modern Cuba, visible in religious practices and secular exchanges.