Depicting his childhood in Trinidad in the opening pages of Beyond a Boundary (1963), C. L. R. James repeatedly makes clear that cricket and the canon of English literature (especially Shakespeare, Dickens and Thackeray) were connected as imperial pillars of his colonial education. He explains how his growing engagement with anti-colonial politics, including the politically aesthetic dimensions of cricket, was bound to his earlier literary development. He also articulates cricket's role in Britain's nineteenth-century domination of the Caribbean, the performative resistance of black players on the margins of the game, and how the racial divide of the plantation and its consequences were visibly enacted and challenged on the cricket pitch long after the 1833 Slavery Abolition Act. As a barrack yard author, cricket writer, Marxist activist and political agitator, James's life and writing drew together cricket, literature and the push towards independence – political, cultural and economic – that the Caribbean basin is still working through. Anthony Bateman has rightly suggested that ‘the legacy of James gave rise to a significant tradition of Caribbean cricket literature, including a particularly rich body of oral and written verse’. While cricket also features heavily in many Caribbean prose works, novels and short stories alike, this chapter shows that we can identify a set of cricket poems from the Caribbean and its diaspora which collectively constitute a tradition of Caribbean cricket poetry that is itself part of the canon of Caribbean writing.