The evolution of jatra is deeply embedded in the social, cultural, and political history of Bengal. The first half of this chapter reflects on jatra as a liberatory performance. More importantly, this chapter demonstrates ways in which sixteenth-century Vaishnava philosophy cultivated a liberative perception within Brahman-centric orthodoxy. This liberatory nature ranges from emancipation and colonialism to social vices, such as caste and religion-based discrimination prevailing in Bengali Hindu society.