Churchill is often ranked as one of the most hated figures in Irish history but he was also one of the most influential politicians in shaping relations both within and between Britain and Ireland. Churchill played a formative role in the ‘Irish Question’. At the beginning of his career he was a Unionist, inheriting his father’s sympathy for Ulster, but converted to Home Rule. The chapter contrasts the impact of social reforms in helping Irish pensioners with the role of Irish suffragettes in defeating Churchill at Manchester in 1908. It looks at how he tried to navigate between the Unionists and nationalists in the Edwardian era, before showing how the war (including Irish losses at Gallipoli) led to rebellion. Thereafter, Churchill pursued a dual strategy of repression and negotiation and played a key role in the Anglo-Irish Treaty and the subsequent events surrounding partition. His belligerence has tended to overshadow the multi-faceted ways he dealt with and thought about the Irish.