As a child, Shaw was horrified by the appalling poverty of the Dublin slums, and, while working in a Dublin estate office as a teenager, he actually had to collect slum rents. On a more personal level, both sides of Shaw’s family were tied to the Protestant Ascendancy, possessing land throughout Leinster and Munster. Although Shaw himself was raised in “shabby genteel poverty,” he was taught to take pride in his family’s exalted social connections. He gradually came to realize, however, that his revered relations were complicit in the unjust land distribution prevalent in Ireland prior to the Land War. The unjust relations between landlords and tenants that Shaw witnessed in Ireland cast a shadow over not only his politics (leading him to embrace socialism as a young man) but also his drama. As this article demonstrates, Shaw deals with Irish landlord-tenant relations directly in his three plays set in Ireland: John Bull’s Other Island, O’Flaherty, V.C., and Tragedy of an Elderly Gentleman. In addition, his exposure to Dublin slums as a child and teenager informs Widowers’ Houses, and his numerous visits to Irish (and not simply English) Big Houses were a clear influence on Heartbreak House.