This chapter examines Eugene Esmonde's family tradition of service in terms of the wider phenomenon of Irish Catholic loyalty. The Esmonde family's history certainly demonstrates that adaptation and evolution to the changing coordinates of Anglo-Irish relations was an essential feature of elite Catholic politics. Loyalty to the crown was deeply ingrained in the Esmonde family's history. After all, the Esmondes claimed descent from Sir Geoffrey Esmonde, who was one of the thirty knights who landed with Robert Fitzstephen in Wexford in 1169. His descendants settled in the southern Barony of Forth, built Johnstown Castle and formed part of the close-knit Old English community which developed in Co. Wexford. The children of John Esmonde who came to adulthood in the early decades of the nineteenth century embodied the transitional circumstances of the Irish Catholic aristocracy at that time.