Sidney, Sir Henry (1529–86), lord deputy of Ireland, was the eldest and only surviving son of the prominent Henrician courtier Sir William Sidney (c.1482–1554) and his wife Anne (nee Pagenham). Sidney commenced a promising career at court in the later 1530s as companion of Prince Edward. Having been made a gentleman of the privy chamber (1548), his position at the very centre of court politics appeared to be consolidated by March 1551 through his marriage to Mary Dudley, only daughter of John, earl of Warwick. Knighted in October 1551, on the occasion of Warwick's elevation as duke of Northumberland, Sir Henry served his father-in-law on at least two diplomatic missions to France, and was regarded as one of his closest supporters. In the summer of 1553, however, he rapidly deserted the Dudley cause, receiving a pardon in June for his actions in the last months of the closing days of the regime. Anxious to rehabilitate himself, he volunteered to serve at his own cost on the earl of Bedford's diplomatic mission to Spain to conclude negotiations for the marriage of Queen Mary with Prince Philip, where he was accompanied by his new brother-in-law, Thomas Radcliffe (qv), earl of Sussex. Sidney's service was undertaken not only to reconstruct his own career, but also, he recorded, to secure the pardon and release of John Dudley, Northumberland's youngest son, and so discharge his debt to his wife's family.
The mission also brought Sidney into closer contact with Sussex, whom he accompanied to Ireland in May 1556, holding senior appointments as vice-treasurer and treasurer at war for Ireland. During his caretaking intervals as lord justice (November 1557–July 1559) Sidney already showed himself willing to depart from his superior, Sussex, making attempts to curtail the army's impositions on the Pale, and entering so seriously into negotiations with Shane O'Neill (qv) as to become O'Neill's blood-brother. This independence of attitude preceded Sidney's renewed association with the Dudley interest under the rising royal favourite, Lord Robert Dudley. But after his departure from Ireland in 1559 to take up the post of president of the council in Wales and the marches, he assumed an important role as adviser to Dudley on Irish affairs. He played a central role during Shane O'Neill's embassy to court (where he insisted on harder terms than was expected), and used his influence to defend the interests of the earls of Kildare (qv) and Desmond (qv), enemies of Sussex whom Dudley was seeking to patronise, and of the agents sent by the gentry of the Pale to complain against Sussex's extortions. There is no evidence that Sidney sought the Irish viceroyalty at this stage, but following the failure of another of Dudley's clients, Sir Nicholas Arnold (qv), as lord justice in 1564–5, Sidney emerged as a principal candidate of the Dudley interest for the permanent replacement of Sussex as Irish viceroy. Raised to the order of the Garter in May 1565, Sidney at first appeared destined to succeed Sussex as lord lieutenant with ease. But his appointment became increasingly contested by friends of Sussex, and it was only after considerable bargaining that he was finally confirmed as lord deputy in October 1565.
This controversial background shaped the character of his first viceroyalty. Richly experienced as a provincial administrator both in Ireland and in Wales, he came to the office with a clear view of his political and administrative priorities, and with a sufficiently strong set of connections to enable him to put them into effect. His first policy statement, embodied in the remarkably full royal instructions which he was heavily involved in drafting, was designed as a comprehensive set of measures designed to transform the political and administrative infrastructure of Ireland. Provincial councils were to be established in each of the provinces; the central courts, the financial offices, and the organisation of the garrison were to be reformed in line with recommendations made by successive reports in the 1560s; and the crown's commitment to the completion of the plantation in Leix and Offaly was to be upheld. These were ambitious but quite conventional proposals. Sidney's real originality rested on more personal grounds: on all aspects he promised to be more efficient and more economical than Sussex had been, and in particular he promised to deal with the outstanding political embarrassment of Shane O'Neill.
This personal commitment supplied a particular edge to Sidney's administration, ensuring that from the beginning it would be subject to hostile attention and persistent criticism from Sussex and his supporters. In this atmosphere, the failure of an audacious but expensive campaign strategy which he launched against O'Neill in 1566, and the destruction through an explosion of the garrison he had introduced at Derry to maintain pressure on Shane in April 1567, made Sidney immediately vulnerable to attack. At the same time his deliberate delay in responding to the queen's directive to arrest Gerald, 15th earl of Desmond, and his brother John (qv) for their part in the feud with Thomas Butler (qv), 10th earl of Ormond, deepened Elizabeth's suspicions that he was placing factional considerations before the interests of the crown, and lost him her confidence. Ordered to arrest the Desmond brothers or face recall, he conceded at length in March 1567. Sidney's difficulties were, however, suddenly relieved by the unexpected defeat of Shane by the O'Donnells in the following May. Anxious to exploit the event Sidney, through his agent William Piers (qv), hurriedly entered into negotiations with the MacDonnells of Antrim to seek their support against the badly damaged Shane; and it is probable that his promise (later reneged on) to recognise them as Irish subjects influenced their decision to kill O'Neill in June.
The fulfillment of this key priority of Elizabethan policy in Ulster allowed Sidney to return to Whitehall with some credit. But almost immediately his proposals for building on this success were buried in a welter of opposing propositions and criticism of his past conduct and current associations with the Geraldine interest, a confusion that was exacerbated by illness, which struck him down in the spring of 1568. Amid all this debate and indecision, the situation of the crown in Ireland deteriorated sharply as Shane's successor as O'Neill (Turlough Luineach O'Neill (qv)) began making himself almost as powerful as his predecessor, and outright rebellion broke out in Munster.
Sidney's solution to this reemerging crisis was even bolder than his earlier strategy against Shane. The long-deferred schedule of political, administrative, legal, and religious reforms would now be initiated not by viceregal instructions but by statutes of an Irish parliament. To this end he began the compilation of a large compendium of draft bills, concerning government policy regarding law and religion, as well as corporate and private interests. At the core of this legislative programme was a set of measures surrounding an act for the attainder of Shane O'Neill, a piece of legislation that was intended to lay the constitutional basis for a massive initiative intended to undermine the legal and customary status of Gaelic lords and enable the English government to deal directly with the landholding families in the lordships. Bedeviled from the beginning by mistrust engendered through Sidney's encouragement of colonisation schemes in Ulster, and his support for the adventures of Sir Peter Carew (qv) in Leinster, Sidney's parliamentary programme met with fierce opposition from the representatives of the Pale, and was soon buried by the crisis provoked by the revolt of Sir Edmund Butler (qv) and the resurgence of rebellion by James fitz Maurice Fitzgerald (qv) in Desmond. The suppression of rebellion in Munster, as well as the emergence of resistance in Connacht to the introduction of a provincial presidency and the need to contain the increasingly powerful Turlough Luineach O'Neill, consumed the bulk of Sidney's time from July 1569 until his departure from Ireland in March 1571, and though some of his proposed legislation was passed (including the O'Neill attainder) the integrity of the programme was lost.
Sidney left Ireland not intending to return. But shortly thereafter, in consultation with his private secretary, Edmund Tremayne (qv), he began a reformulation of the policy of restructuring the distribution of power in the Irish lordships by means of executive action alone. This strategy, which envisaged the threat of massive military exactions on a provincial scale in order to negotiate the commutation of all military exactions between and within the lordships, was termed ‘composition'. The term, denoting a bargain, was currently in use in England for similar commutation of feudal dues into agreed cash rentals. But the strategy had distinctively Irish origins in Sidney's contrasting experience of his failure to secure legal and fiscal change by legislative means, and the striking success of his captains in establishing themselves as powerful figures in the provinces by the sheer emulation of the practices of intimidation, force, and personal diplomacy by which the native lords had ruled. Though Sidney began canvassing for office on the basis of the strategy of ‘composition’ as early as 1572, his reappointment faced serious opposition at court, and he was forced to make a number of concessions concerning costs and time which severely constrained the efficiency of the policy, and substantially increased its risks. His attempts on his arrival in Drogheda (8 September 1575) to initiate a form of composition in the Pale, in lieu of the army's irregular exaction of ‘the cess', immediately provoked resistance. The conduct of his agents Sir Nicholas Malby (qv) and Sir William Drury (qv), appointed presidents in Connacht and Munster respectively, likewise produced widespread unrest throughout 1576 and 1577. But while Drury achieved considerable success in advancing composition in Munster, and Malby, by ruthless tactics, had succeeded in isolating the Clanrickard Burkes in Connacht, the most serious challenge arose in the Pale, from whence agents were dispatched to Whitehall to plead the unconstitutional nature of Sidney's conduct. At first unimpressed by this challenge to the royal prerogative, Elizabeth became convinced, partly through the advice of Sidney's own lord chancellor, Sir William Gerrard (qv), and partly by the rising costs of his administration, that Sidney had exceeded his legal powers over her English subjects in the Pale. Sidney was ordered to negotiate an alternative arrangement. This effectively destroyed Sidney's plans for a national policy of composition; and when his recall was finally confirmed in May 1578, he made no attempt to oppose it.
The course of Sidney's attempts to advance religious and ecclesiastical reform in Ireland followed a similar pattern. The viceregal instructions of 1565 included an elaborate, if conventional, agenda for the advance of ecclesiastical reform. In 1567 he published a slightly adapted form of Archbishop Parker's moderate eleven articles (1561) as a provisional constitution for the Church of Ireland, and he hoped to sustain the force of his initiative through key episcopal appointments in Armagh, Dublin, and Cashel. But Sidney's plans were disrupted by his preoccupation with more urgent military imperatives and, more importantly, by the blockage of most of his appointments, most notably Terence Danyell to Armagh and Hugh Brady (qv) to Dublin. Again several bills concerning ecclesiastical reform were included in his parliamentary programme in 1569, but these too were dashed, along with his highly ambitious plan for the funding of an Irish university. Sidney's frustration with the ecclesiastical establishment – and especially with Archbishop Adam Loftus (qv), whom he believed had actively obstructed his earlier plans – led him to undertake a bold initiative on his return to Ireland in 1575. By establishing a court of faculties and a new high commission under his own direction, Sidney sought at once to override the authority of the bishops and also to launch a campaign for the enforcement of conformity among the clergy and laity of the Pale. Coinciding with his implementation of ‘composition', this use of the royal prerogative only strengthened resistance to his government in the Pale, and reinforced the case that he was acting above the law. On his recall the new courts were placed under the authority of Archbishop Loftus.
Though embittered by his experience, Sidney did not abandon hope of returning to Ireland. In 1582 he was again angling for office, though his demands on this occasion, which included a substantial grant of land and a peerage, were unacceptable to Elizabeth, and he resigned himself to political exile, retaining his office as lord president of the council in Wales and residing at Ludlow castle, where he died 5 May 1586. Portraits in oils, attributed to A. Bronckorst, are at Petworth House, West Sussex, the National Portrait Gallery, London, and Penshurst, Kent.
Sidney's initiatives in secular and religious policy were reflections of his increasing frustration with the conventional political, legal, and administrative structures of his day. There are hints – in his proposals to impose taxation without parliamentary consent, his establishment of powerful regional governors, and his willingness to exempt compliant nobility from taxation – of a drift in his thinking on Ireland toward a form of government that would later be recognised as absolutism. But if so, Sidney himself was largely unconscious of it. He wrote no general treatise on policy beyond his several position papers and memos, and his invaluable ‘memoir of service’ is a narrative written primarily to put some order on his tumultuous and controversial experience in Ireland.