The Betting Act 1926 legalised cash betting in Ireland and led to the appearance, for the first time, of the legally regulated and licensed betting office. The introduction of this legislation was a pragmatic step, designed to eradicate the undesirable practice of street bookmaking. This article seeks to examine the operation of the legislation over the entire period of its enactment before it was superseded by the Betting Act 1931. What follows focuses on the bookmaker, their social background, geographical distribution, clientele and business practices. The industry, as it made its transition from its illegal to regulated forms, was characterised by both continuity and change. How bookmakers were perceived in the context of the puritanical atmosphere of the Free State is also considered. Attitudes to bookmakers depended on the scale of their involvement in the business, where they conducted their business, and who they conducted it with. Debates featuring these issues were spliced with contemporary concerns about class, gender and youth.