This dissertation presents a multifaceted social and commercial history of Sackville (later O’Connell) Street – Dublin’s principal thoroughfare – between 1782 and 1930. Over the course of six chapters, the evolution of Sackville Street as the principal commercial thoroughfare and as the most significant public space in Dublin for the expression of often contested political identity and organised protest is examined. In the late eighteenth century, following a long political struggle, the central axis of Dublin moved eastward away from Essex Bridge, the stronghold of elite merchants. The construction of Carlisle Bridge and the extension of Sackville Street to the river set the scene for the rapid commercial expansion of Sackville Street. Further infrastructural change – the location of the new General Post Office, the widening of the Carlisle Bridge and the creation of one of the most modern light rail systems in Europe, among other factors ¬– consolidated Sackville Street’s commercial significance. A novel feature of this dissertation is the creation of bespoke databases of business listings drawn from commercial almanacs and contemporaneous newspapers. This has permitted the construction of a detailed profile of the retailers and services on Sackville Street over the long nineteenth century. A key finding is that the predominance of retail on the street gave way over time to services, particularly those associated with the law. Sackville Street’s long pedigree as a site of protest helps explain its prominence as the epicentre of the Easter 1916 Rising and site of bombardment at the beginning of the Irish Civil War. As a result, almost the entire street was destroyed. Utilising compensation records, the final section examines how first the British and then the Irish government devised compensation schemes to enable the reconstruction of Sackville Street.