Cowley, Robert (d. 1546?), government official, was the son of Walter Cowley. His origins are uncertain: the near-contemporary Book of Howth states that he was born in England, but the name Cowley was common in Kilkenny city from the start of the fifteenth century; perhaps he was from an English branch of the Cowley family and was attracted to Ireland by family connections there. Besides the commonest form, his name is variously spelt Coule, Cole, and Colley. He appears to have had some legal training and may have attended Lincoln's Inn, London, in 1502. In 1505 he appears as customer of the port of Dublin, a post he still held in 1520; he resided in the city, where he was also a merchant, and was admitted a citizen in January 1506. By then he was secretary to Gerald (Garret Mór) FitzGerald (qv), 8th earl of Kildare and lord deputy of Ireland, who also appointed Cowley to his baronial council. His closeness to Kildare enabled him to secure lucrative government contracts to import goods from England on behalf of the crown. By 1513 he had at least six ships.
After Kildare's death in 1513, his son and successor to both the earldom and lord deputyship, Gerald (Garret Óg) FitzGerald (qv), dismissed Cowley from his council (c.1513–15). Cowley then became servant to Lady Margaret Butler (qv), sister of Garret Óg and wife of Piers Butler (qv) of Pottlerath, later earl of Ossory and 8th earl of Ormond. Around this time Butler and his wife fell out with Kildare over Kildare's refusal to support Sir Piers's claim to the earldom of Ormond. Contemporaries believed that Cowley played a key role in bringing about this momentous rupture between the two dynasties, though other factors appear to have been more important. Thereafter Butler managed in a remarkably short period of time to re-establish the Butler lordship in Kilkenny and Tipperary as a rival to the previously hegemonic Kildare lordship. This development was supported by the crown, which wished to reduce the Kildares’ dominance over Irish politics. Cowley became Butler's legal adviser and envoy to London.
In 1519 Cowley travelled to London to accuse Kildare of abusing his position as lord deputy to advance his own personal power at the expense of both the king and the increasingly beleaguered English colony in Ireland. As a result of Cowley's deposition Kildare was dismissed and replaced by an English governor. Cowley was clerk of the privy council in Ireland in 1520–24, but presumably relinquished this post when Kildare was restored to the governorship in late 1524. In that year Cowley returned to London to promote Butler's efforts to be recognised as earl of Ormond and to present articles against Kildare. During the 1520s he advised Henry VIII's chief minister, Cardinal Thomas Wolsey, on Irish affairs, a relationship he would replicate in the 1530s with Wolsey's successor, Thomas Cromwell. In February 1526 he became gauger of Ireland, excluding the Pale. About 1525, after intercepting treasonable correspondence between Kildare and the rebel earl of Desmond, he returned to England to discredit Kildare once more. There he remained for a year, successfully proving these charges against Kildare, who was detained in England until 1530. On his return to Ireland, Cowley moved from Dublin to Brownestown, Co. Kilkenny, in the heart of Butler's lordship where he was safe from Kildare's supporters, who had previously attacked his property.
In 1532 he informed royal officials that the liberty of Kildare had lapsed in 1432 and that its revival in 1502–6 had been illegal. This information contributed significantly to the crown's decision in 1534 to abolish the liberty, an act that precipitated the rebellion of Thomas FitzGerald (qv) (‘Silken Thomas’) and the subsequent destruction of the Kildares after his defeat in 1535. In 1536 Cowley moved to Dublin in order to pursue a career in the central administration and was appointed customer of Dublin port and clerk of the crown. In 1538 he was granted confiscated monastic property at Holmpatrick in Co. Dublin, where he established his residence. He also appears to have been an MP in the 1536–7 Irish parliament.
During 1535–6 the government was uncertain how to deal with the many FitzGerald sympathisers within the Pale and with their Gaelic allies further afield. Cowley urged a ruthless prosecution of FitzGerald supporters and, in a treatise written for Cromwell in summer 1536, called for a radical policy of conquest and colonisation in Leinster against the Gaelic Irish there. His objective was to maintain Ireland in a state of war in order to make the crown more dependent on the Butlers for military support. In the event of peace the government was more likely to demand that Butler reform and demilitarise his own lordship. Cowley argued that Anglo-Irish magnates should be allowed to retain their private armies until the Gaelic Irish had been destroyed. However, Cromwell rejected the policy of conquest because of the expense involved. Worse still, the lord deputy, Leonard Grey (qv), was unwilling to be a Butler puppet and favoured the FitzGeralds’ supporters, whom he hoped to play off against the Butlers. Cowley criticised Grey repeatedly, but failed to secure his removal. Despite this setback, he was made master of the rolls on 2 January 1539 and granted a royal pension in 1541.
In July 1540 Cowley wrote to London complaining that the vice-treasurer, William Brabazon (qv), was embezzling royal revenues. A royal commission was dispatched to Ireland to investigate, but found only minor irregularities in Brabazon's accounts. Dissatisfied, Cowley compiled a detailed list of charges against Brabazon and sent them to London in December. By 1541 the Butlers had decided that the new lord deputy, Sir Anthony St Leger (qv), was not sufficiently beholden to their interests, and Cowley broadened his corruption charges to include St Leger. His case was strong but politically ill advised, given that virtually the entire Irish government, including his patron the 9th earl of Ormond, was implicated in the corrupt sale of former monastic lands. The government closed ranks behind St Leger and a now isolated Cowley travelled to England in autumn 1541 without permission to pursue his vendetta; he accused St Leger of declaring that Henry VII (the current king's father) had been an illegitimate king and stated that all the leading members of the Irish government had stolen crown lands and revenues. The English privy council heard his charges on 17 October 1541 and then imprisoned him while it considered his allegations. On 14 April 1542 the king branded him a troublemaker, dismissed him as master of the rolls, and later returned him to prison. He was released on 21 July 1543, but appears to have been refused permission to return to Ireland. In January 1545, he was deprived of his lease of Holmpatrick. He had become totally blind by the time of his death, which occurred in London, probably in 1546.
With his wife, Anne, he had three sons and a daughter. His eldest son, Walter Cowley (qv), served as principal solicitor of Ireland; Robert received lands in the plantation of King's County but was killed by rebels in 1572; and Nicholas was a merchant of Kilkenny, being mayor of the city in 1540 and 1541.