The Indian Maoists and the largest contingent of India’s parliamentary Left started their political journey on two divergent paths from the late 1960s. The Indian Maoists aim to capture political power with an armed rebellion. In contrast, the parliamentary Left identified electoral democracy as a site of political struggle necessary to change socio-economic conditions in India. Five decades later, when India has gradually transformed from an old order state-managed capitalism to corporate-led neoliberalism, what does it mean to be radical in contemporary India? Has the radical transformation of capitalism in India exposed the limit of the promise of the Maoists and the parliamentary Left? Has the success story of Indian capitalism questioned the basic premise of the Maoists of fighting the capitalist nation-state with its armed strategy? Do the Indian Maoists and the Indian Parliamentary Left need to learn from the global experiences of successes and failures of specific political strategies? This chapter will deal with such questions by analysing the ideological discourses of Maoism and the debates between the Maoists and the parliamentary Left in India as well as examining the radical politics of the Maoists in contemporary India.