The first three decades of the twentieth century saw a gradual pacification among the rebel Mayas of Yucatan, who for over half a century had struggled against both Yucatecs and Mexicans. As they accepted the reconcilatory measures of Mexico's succesive revolutionary governments, they also got involved in the capitalist exploitation of gum. However, this process developed not only because of state's and capital's incorporating pressure, but also due to Mayan society's rationale of trying to preserve their autonomy. By examining the activities of Francisco May, the most important Mayan leader of that time, this paper describes how Mayas cleverly negotiated with the outer world, and clarifies the duality in the position of Mayan leaders, who acted as mediators between two worlds.