This article explores the impact of illegitimacy upon the social, judicial and political landscape of the North of England, from the late medieval period to the eve of the English Civil War. Historiographies of the gentry and of marriage might suggest that irregular unions and resulting bastardy were increasingly frowned upon and of declining significance. At a time when civil strife and Reformation settlements altered the political structures of the North of England and provided alternative approaches to office holding, social and religious commentators expressed concern about the ordering of society at elite levels. In the face of that, this article considers some of the evidence which suggests the extent of bastard-bearing among the elite throughout the period. It further demonstrates the degree of acceptance of this phenomenon among gentry families, including the inheritance of land, property and goods, and involvement in informal political networks, and demonstrates that base-born sons of the nobility and gentry were often accepted into the Church and ranks of northern officialdom, holding highly localised but strategically important offices as Wardens of the Marches in the far North and acting as Justices of the Peace.