Dillon, Sir Robert (d. 1597), judge, was the eldest son of Thomas Dillon of Riverston, Co. Meath, and his wife Anne, daughter of Sir Thomas Luttrell (qv), chief justice of the common pleas. He studied law at Lincoln's Inn, appearing as escheator there in 1560. In 1562 he was among a group of Irish students at Lincoln's Inn who signed a protest at the quartering of royal troops on the Pale. This youthful and public rebelliousness contrasts with his subsequent career, characterised mainly by calculated loyalty to the crown.
Early official career He was called to the bar (1567) and, after practising law with some success, was appointed second justice of the presidency of Connacht (1 June 1569), thereby perpetuating a family tradition of public service. In November 1570 the chief justice of Connacht, Ralph Rokeby (d. 1596), left Ireland permanently, leaving Dillon to carry out his role. As such, he emerged as the right-hand man to the president of Connacht, Sir Edward Fitton (qv), being engaged in overseeing judicial sessions throughout the province. The formation of the presidency of Connacht, and Fitton's ensuing efforts to establish English law in the province, aroused intense opposition. As a result, Dillon often found himself accompanying Fitton on campaigns against recalcitrant lords during 1570–72, leading the president to praise him for his resolve, particularly as he had no previous military experience. Eventually (summer 1572) a widespread and sustained revolt in Connacht drove Fitton and his entourage out of the province.
Both Dillon and Fitton blamed the lord deputy of Ireland, Sir William Fitzwilliam (qv), for failing to support them and plotted his downfall. Despite the humiliating end to their governorship of Connacht, the duo remained influential – Dillon was made chancellor of the exchequer on 5 June 1572, in which capacity he continued to work alongside Fitton, who became vice-treasurer of Ireland in January 1573. In early 1573 Dillon went to London to try to secure some reward for his service and to complain against Fitzwilliam, but achieved little. On his return he avoided Fitzwilliam's presence, such was the lord deputy's animosity towards him. As well as being chancellor, he was formally appointed chief justice of Connacht (18 June 1573), and he and Fitton continued to oversee occasional judicial sessions for Connacht at Athlone down to 1575, although in practice their rulings were largely disregarded.
By about the middle of 1574 Fitton and Fitzwilliam, having failed to dislodge each other, came to an accommodation, leading to a corresponding improvement in Dillon's relationship with the lord deputy. Indeed, in November 1574 Fitzwilliam entrusted Dillon with covertly investigating claims that Gerald Fitzgerald (qv), 11th earl of Kildare, had orchestrated rebellions against the crown in the midlands. Given that Kildare was the most powerful nobleman in the Pale and a client of the queen's chief favourite, Robert Dudley, this was a highly sensitive matter. The Dillon family was known to be strongly anti-FitzGerald, which (combined with Robert's unscrupulousness) commended him to Fitzwilliam, who was determined to make the earl a scapegoat for the failures of his own viceroyalty. Dillon's investigations culminated in Kildare's arrest for treason in May 1575. That September, he went to London to brief the English privy council on the ultimately unsuccessful case against Kildare.
Protestantism and advancement By the mid 1570s Dillon had impressed his government colleagues not only with his legal ability, but also with his staunch protestantism. In 1572 the Church of Ireland archbishop of Dublin, Adam Loftus (qv), praised him for assisting the work of the court of ecclesiastical commission, which prosecuted catholics for not attending protestant church services. As the crown's fiscal and religious policies became progressively more intolerable for the traditionally loyal Anglo-Norman population of the Pale, Dillon stood out as a rare example of a man of Irish birth who could be relied on. Indeed, he aligned himself politically with the most hard-line elements within the Irish government, being particularly close to Loftus and proved himself to be unconcerned about incurring the hostility of his neighbours in executing unpopular government policies in his role as a leading member of various local government commissions in Co. Meath.
As a result, he rapidly ascended the judicial ranks, becoming second justice of the court of common pleas on 26 November 1577. In practice he ran the court of common pleas, as his elderly and infirm grand-uncle and namesake Sir Robert Dillon (qv), who was its chief justice, delegated this role to him. In late 1579 his grand-uncle died; Dillon expected to succeed him as a matter of course, but reports of his intended promotion infuriated Kildare, who (doubtless recalling Dillon's role in his arrest in 1575) warned that he would refuse to serve the government if his bitter enemy received such advancement. In a bid to placate Kildare, the government passed Dillon over, appointing Nicholas Nugent (qv) instead. This development was deeply galling for Dillon. A long-standing enmity existed between the Dillon and Nugent families, who vied acrimoniously for dominance of the Meath–Westmeath region and for jobs in the royal administration. Both reflecting and intensifying this rivalry, the families chose opposite sides in the increasingly unbridgeable divide that had opened up between crown and country, with the Dillons emerging as staunch loyalists, while the Nugents became prominent in the constitutionalist and catholic opposition to the government within the Pale. On a personal level, Dillon had come to blows with his fellow student Nicholas Nugent in 1560 during his time at Lincoln's Inn.
The outbreak of a catholic rebellion within the Pale in summer 1580 caused panic and suspicion in official circles, and this, combined with the simultaneous appointment of a militantly protestant lord deputy, Arthur Grey (qv), with whom Dillon immediately formed a close relationship, enabled him to turn the tables on his hereditary foes. The Dublin administration adopted harsh repressive measures against its opponents, both real and imagined, within the Pale, as the Dillons and their English protestant patrons exploited fears of a catholic conspiracy to settle old scores and further their own interests. In spring 1581 Dillon went to London, where he successfully undermined Nugent, supplanting him as chief justice of the court of common pleas on 14 July. During Grey's lord deputyship, a number of Dillon's family gained high public office, including his brother Gerald, who was made clerk of the crown, and his relative Thomas Dillon, who became chief justice of Connacht.
Indicative of Dillon's membership of Grey's inner clique is A discourse of civill life by Lodowick Bryskett (qv), which was published in 1606 but purports to relate a discussion between Grey's closest supporters in spring 1582. All the protagonists see themselves as an embattled elite, striving to impose peace and civility on a barbarous country. All are protestant, with Dillon being the sole Irishman present. He plays a prominent role in the discourse, where Bryskett casts him as a veritable man for all seasons, quoting classical authors, speaking with authority on education and theology, and making witty jokes. Although undoubtedly fictitious, it reflected the manner in which Grey and his circle idealised Dillon as the ‘good Irishman’, implicitly contrasting his loyalty and learning with the treachery and backwardness of his compatriots.
The Nugents In autumn 1581 Dillon played a key role in investigating a plot against the government, instigated by William Nugent (qv), which allegedly embraced a wide cross-section of Pale society. For his efforts, Grey knighted Dillon on 17 November. Meanwhile about twenty landowners were executed for treason during 1581–2, the most prominent victim being Dillon's foremost rival Nicholas Nugent, who was a cousin to the rebel leader William Nugent. It appears as if Dillon suborned one of the genuine plotters, John Caro Cusack, to implicate Nugent in return for securing his pardon. At a special trial held in Trim (4 April 1582), the jury initially acquitted Nugent and his co-defendant; but, backed by the menacing presence of royal soldiers in the courtroom, Dillon, who was one of the judges, intimidated them into reversing their decision. The unfortunate Nugent was hanged at Trim two days later.
The widespread outrage within the Pale that accompanied the executions of Nugent and others provoked a reaction in the royal court against Grey and the Dillons. Grey was questioned from London about payments he had authorised to Dillon and was recalled as lord deputy in summer 1582. This diminished Dillon's political influence, although he remained a leading government official and jurist. The government called a halt to the trials and executions in the Pale, and in 1583 Dillon was forced to pay £300 in compensation for seizing his goods to Edward Cusack, who had been convicted alongside Nicholas Nugent, but had not been executed and was later pardoned by the queen. In pardoning Cusack, the queen was admitting indirectly that Nicholas Nugent had been innocent of treason. Regardless, Dillon continued to harass the Nugents whenever the opportunity arose, especially the head of the family, Christopher Nugent (qv), Baron Delvin, who found it impossible to secure a speedy resolution to a number of long-running and expensive lawsuits in Dillon's court.
In May 1583 Dillon engaged in rancorous and unsuccessful negotiations with representatives of the Pale landowners at Navan, regarding the crown's demands for supplies for its armed forces. By then, his widespread unpopularity made him wholly unsuited for any kind of mediating role between the government and the Palesmen. This was not the case in the rest of Ireland, where he and other members of his extended kin formed financially lucrative ties with powerful Gaelic families who, finding themselves being drawn within the crown's ambit, urgently needed influential patrons at the administrative centre. Dillon appears to have taken money from leading members of the O'Farrells in Longford, the O'Carrolls of Offaly, the O'Connors of Sligo, the O'Reillys of Cavan, the O'Neills of Tyrone, and the O'Rourkes of Leitrim. All things being equal, he tended to promote coercive religious and military measures, especially within the Pale, but his sideline as advocate for certain Gaelic lords often caused him to advocate diametrically opposed policies. His competing political interests, combined with his propensity to engage in personal vendettas with his government colleagues, contributed to his increasingly erratic political behaviour during the 1580s.
From 1583 he clashed with the secretary of state, Sir Geoffrey Fenton (qv), then in late 1584 he was embroiled in a dispute over precedence with the master of the rolls, Sir Nicholas White (qv). His relationship with Sir John Perrot (qv), lord deputy of Ireland 1584–8, was uneasy, but Perrot tolerated him due to his high regard for his relative, Sir Lucas Dillon (qv), chief baron of the court of exchequer. Moreover, like Fitzwilliam before him, Perrot struggled to impose his authority over his fractious subordinates and found uses for Dillon's willingness to engage in the dark arts of politics. In January 1587 and at Perrot's behest, Dillon had their mutual enemy Fenton arrested on a trivial charge of non-payment of debt and brought before the court of common pleas, where he was tried, convicted, and imprisoned within the space of fifteen minutes. Perrot also used the Dillons to undermine the president of Connacht, Sir Richard Bingham (qv), whose ruthless conduct often provoked the armed opposition of Gaelic clans in the province, many of whom were Dillon clients.
Away from these political tribulations, Dillon emerged as the richest commoner in the Pale by the mid 1580s. He had inherited a sizeable estate from his father, but undoubtedly he added significantly to this by accepting bribes and by the self-interested mismanagement of the judicial process. However, the ruthless and at times reckless abuse of political authority that had been required to achieve this wealth had also earned him the hatred of many influential figures within and without the royal government. It also provided these enemies with the ammunition to fashion his ruin, given the right political circumstances.
Fitzwilliam's second term In autumn 1588 Fitzwilliam was reappointed lord deputy in Perrot's stead, and Dillon soon emerged as one of his key lieutenants, their past rivalry long forgotten. This is not surprising given that during his second term of office Fitzwilliam governed Ireland in a cynical, opportunistic, and above all else corrupt fashion, something that complemented Dillon's preferred modus operandi. As events transpired, Fitzwilliam proved far more dangerous as a friend than he had ever been as an enemy. In spring 1589 Dillon was appointed commissioner to pacify Connacht, where a rebellion had broken out against Bingham. As such, his brief was to discredit Bingham's governorship of the province by fair means or foul. However, trusting too much in Fitzwilliam's influence, he appears to have overreached himself, and his evident bias earned him a royal rebuke in July. Worried that his manipulation of rebellious Gaelic clans in order to advance his factional and financial interests could leave him exposed to charges of treason, he sent gifts to a number of privy counsellors in London in August in a bid to shore up his position. Later that year, he was specifically barred from being one of the judges appointed to consider a number of charges against Bingham, and allegations that he received bribes from a number of Gaelic lords were taken seriously for the first time.
In the event, his patron Fitzwilliam unwittingly encompassed his near-demise by accusing Perrot of treason in February 1590, thereby precipitating a major political crisis that eventually drew the queen's attention towards Dillon's many dubious political and judicial machinations. Initially, Dillon had not been involved in the concocted treason charge, but once it became apparent that the queen was prepared to countenance Perrot's downfall, he emerged in summer 1590 to play a leading role in accumulating prosecution evidence. In doing so, he was playing with fire, given that one of the main accusations against Perrot was that he had encouraged the Connacht lord Brian O'Rourke (qv) to rebel in 1589, and given Dillon's own close links with O'Rourke and murky involvement in Connacht politics during that period. Moreover, Fitzwilliam also accused Perrot of relying on the sinister advice of Irish-born counsellors, sparking a witch-hunt against all Irishmen holding public office. The Nugents, having rehabilitated themselves in official circles, seized their chance to avenge themselves by accusing Dillon on 4 August 1591 of abetting and being in the pocket of known rebels, and of abuse of public office. Fitzwilliam was in a difficult position as he had to be seen to pursue the matter in a non-partisan fashion. Moreover, the controversy still surrounding Dillon over his role in Nicholas Nugent's execution in 1582 and in the 1589 Connacht commission lent weight to these allegations.
On 6 August Dillon was imprisoned in Dublin castle, but was released in early September on condition that he remained within the city limits. He used this freedom to bribe and threaten witnesses, thereby defeating the initial charges presented against him. However, in September, the queen expressed an interest in Dillon's case, immensely complicating his and Fitzwilliam's efforts to clear their names. In November the English privy council rebuked Fitzwilliam for obstructing Dillon's prosecution and ordered that the charges against him be reexamined. He appears to have been suspended from office and from attending privy council meetings, placed under house arrest, and ordered to confer solely with his family and servants. Fresh evidence and allegations were presented in February 1592 to a Dublin-based royal commission, which proceeded to interrogate witnesses from 14 April to 13 June. The commissioners were allies of Dillon, but – aware that the queen's eyes were on them – they proceeded cautiously and indecisively, referring the evidence to London.
In the autumn his position deteriorated further when former servants of Brian O'Rourke deposed that Dillon had advised their master to rebel in summer 1589. This may well have been the case, and if so it was almost certainly done at Fitzwilliam's instigation in order to discredit Perrot, with whom O'Rourke had been aligned. This would account for the desperation with which Fitzwilliam continued to defend his client, often defying the queen's express commands in doing so, by stressing in his dispatches Dillon's importance to the running of his administration, threatening witnesses, passing confidential prosecution material to Dillon, and arresting one of the prosecution lawyers on a trumped up charge. On one occasion, when the lord deputy presided over a meeting of the Meath gentry, he caused astonishment by having the then disgraced Dillon ride alongside him in full view of the assembly.
Final years: changing royal attitudes Although Dillon could rely on the support of most of his government colleagues in Dublin, the chief royal minister Lord Burghley, perhaps taking his cue from the queen, facilitated the Nugents in their relentless harassment of Dillon. On 10 April 1593 Dillon was dismissed as chief justice of common pleas while being allowed to remain on the Irish privy council. Nonetheless, his foes grimly pressed for his prosecution and in June London ordered further investigations into his dealings with O'Rourke. That autumn the commission investigating the Nugents’ claims cleared Dillon of all charges and he resumed his public duties on 27 November, when he was appointed to an ecclesiastical commission. On 30 January 1594 he was formally pardoned by the queen.
The queen's change of attitude may owe much to the growing realisation that the purge of Irish officials during 1590–92 had deprived the state of its most effective intermediaries with the Gaelic lords in Ulster, who had formed a formidable confederation and were poised to rebel. Dillon was a long-standing associate of the leader of the Ulster confederation, Hugh O'Neill (qv), 2nd earl of Tyrone, and it may have been hoped he could use his influence with Tyrone to bring about a peaceful settlement. Significantly, he was immediately appointed to ride the assize circuit in Ulster, although in practice this probably entailed negotiating with various northern lords rather than presiding over court sessions, such was the condition of the province at the time. His comeback was complete on 15 March 1595, when he was reappointed chief justice of common pleas, on which occasion the queen declared that she now realised that the charges against him were without foundation.
In the event, Tyrone led his confederates into a rebellion that slowly gathered momentum during 1594–7, and Dillon's perceived closeness to the rebel chief caused many loyalists to view him with suspicion. Indeed, in February 1596 a government informer specifically requested that his intelligence should not be communicated to Dillon. He died 15 July 1597 at his home in Riverston and was buried at the church in Tara, Co. Meath. His will, which was drawn up in 1593, suggests that, despite some ambiguity in its wording, he continued to identify strongly with the protestant religion.
He married first Eleanor, daughter of Thomas Allen of Kilteel, Co. Meath, with whom he had one son who predeceased him, and after her death married Katherine, daughter of Sir William Sarsfield (qv) of Lucan, Co. Dublin; they had five sons and nine daughters. Neither marriage can be dated.