The life of Annie Besant (1847–1933) is marked by a remarkable spectrum of engagements which entailed numerous crossings of borders and boundaries demarcating social, cultural, ideological, geo-political as well as gender distinctions. During her early career she was a prominent supporter of rationalism, atheism, women’s rights, birth-control, and socialism. She later turned to Theosophy and settled in India, where she became the President of the Theosophical Society and an important figure in the Indian independence movement. Her biography can to a considerable extent be seen as a self-referential blending of political, spiritual and trans-cultural endeavours. While the combination of the political and spiritual is a feature of Besant’s biography that is shared with other contemporary intellectuals and leaders, it gains an additional complexity as it dove-tails with an explicit trans-cultural endeavour concerned with translating ideas and terms from one culture into another, and proposing it as a solution to what she regarded as a crisis of colonialism and materialism, as well as of ancient values. The complexity of the constellations she has entered as well as created can be seen as resulting from her criticising and crossing boundaries at different levels. Her critique of bars and borders is often fuelled by the claim to interconnect realms that are usually kept apart. These different levels produce not only a multilayered discourse, but also a biography no less complex. Rather than it being made up of a sequence of neat phases, it seems to consist of co-existing fields of engagement and is characterized by a trans-cultural dimension as well, since Besant made the joining of cultures not only her agenda, but viewed herself as being the embodiment of such mediation.