Leonard was born in January 1962 in Westow, East Riding of Yorkshire and raised in the market town of Malton, North Yorkshire. He is the son of Derek, a tailor and member of the Tailor and Garment Workers Union, and Janet, who looked after him and his two sisters. From the age of 11, he was educated at the independent, fee-paying Pocklington School in the East Riding of Yorkshire, having received a local education authority scholarship. As a young boy, his first job was picking potatoes in Autumn. He was inspired politically in his youth by Arguments for Socialism written by Tony Benn, a leftist Labour Member of Parliament and former cabinet minister. He was further influenced by Farewell to the Working Class and Critique of Economic Reason by Austrian philosopher André Gorz, as well as the works of early socialist novelist William Morris.
