Rudyard Kipling is considered to be one of the most popular but also one of the most controversial figures in British literature, most notably for being a colonialist. As an Anglo-Indian man, Kipling travelled between the two nations of Britain and India, and his difference from the native Indians shaped his opinions on the colonisation of India. He expressed his views on colonisation in many of his works, including his most well-known two short story collections, The Jungle Book (1894) and The Second Jungle Book (1895). This paper explores the allegory of colonialism and imperialism in the short stories about the main character, Mowgli, the boy who was raised by wolves in the jungle, through the different animal groups, and the protagonist himself, who embodies the dual identity and the traumatic childhood of the author, presenting the readers the fantasy of a hurt Anglo-Indian man who advocates for the domination of others.