Gerald of Wales was about twenty years old when John, youngest son of Henry II, was born and he outlived him by seven years or so. They probably first met in or soon after 1184, the year when Gerald, at the time archdeacon of Brecon, entered royal service; John was then sixteen. Thirty-two years later, in the last year of John's life and reign, Gerald was composing verse welcoming the arrival in England of the king's adversary and would-be supplanter, Louis of France. In the three intervening decades, Gerald had accompanied John on his unfortunate expedition to Ireland in 1185, painted a detailed pen-portrait of the young prince, recorded many personal conversations with him, supposedly declined the offer of several Irish and Welsh bishoprics from him, had a four-year struggle with him over his election to St Davids (1199–1203), during which he had been declared an enemy of the king, had a reconciliation, offered the king advice on a second expedition to Ireland, and then finally settled down in retirement to excoriate John as the worst of tyrants.

Gerald first turned his pen to John in two works that were published in 1189: the second edition of the Topographia Hibernica and the Expugnatio Hibernica. The former contains several chapters, not found in the first edition of the Topographia, presenting both physical and psychological portraits of the four sons of Henry II, while the latter includes an account of the Irish expedition of 1185 and analyses the causes of its failure. In this second edition of the Topographia John shares a chapter with his older brother Geoffrey, ‘the Breton and the Irish’ as they are titled, as Geoffrey was count of Brittany and John lord of Ireland. It should be noted that, although Geoffrey died in 1186, this passage is in the present tense: