The Williamite confiscation was the last of the major land settlements in seventeenth-century Ireland. Each settlement had provided unprecedented opportunities for accelerated social mobility which was impossible under normal conditions. The disposal all at once of so much confiscated land (620,000 Irish acres) created a buyers’ market, creating opportunities for the ‘speculative and strong willed’. The most speculative and strong-willed adventurer in the 1690s was William Conolly. In 1688 Conolly was a busy but unremarkable Dublin attorney. The Williamite war and its aftermath, however, had a profound effect on his career especially the opportunities to gain riches and influence through investment in forfeited Jacobite estates. In 1703 his rental income was reckoned to be approximately £4,000 p.a. Virtually all of this came from property purchased in the 1690s. These included forfeited Jacobite estates spread across five Irish counties as well as others purchased at depressed prices due to the effects of the war and the resultant oversupply in the Irish land market. Conolly also acquired a reputation for shrewd dealing (or sharp practice depending upon the viewpoint of the observer); the Trustees of Forfeited Estates allegedly described him as a ‘cunning intriguing spark’ in 1701, while Joseph Addison referred more favourably to his raising of a great estate ‘without the advantages of birth or education’. His acquisition of a large fortune in such a short period of time provoked, almost inevitably, questions and innuendo about the means by which he had acquired this fortune, questions which have continued to dog his reputation.

J. G. Simms, in his authoritative history of the Williamite confiscation noted that ‘Conolly’s rise from obscurity has always been a puzzle and that it could not be solely ascribed to his trafficking in forfeited estates, although he certainly made a great deal of money out of them.’ Later historians have been content to follow him in noting Conolly’s rapid accumulation of land and wealth but failing to analyse the methods by which they were acquired. Hayton has referred to Conolly’s ‘mushroom fortune, which was thought to have its origins in trafficking in forfeited estates’, while McNally merely states that Conolly’s fortune was founded upon successful land speculation.