Colliding worlds? Shane the Proud and the advance of the Tudors in Ireland

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A rather fanciful 19th century depiction of Shane O’Neill.

By John Dorney

 In 1562, Shane O’Neill, lord of the powerful O’Neill dynasty in Ulster, arrived at the Court of Queen Elizabeth I in London. He was, one writer tells us, ‘attended everywhere by his guard of gallowglass [gal oglaigh, Scottish Gaelic mercenary soldiers] armed with axes, bare headed, with curled hair hanging down… whom the English people gazed on with no less admiration than they do nowadays them of China or America’.[1]

According to one exasperated English Lord Deputy, ‘I believe that Lucifer was never puffed up with pride more than O’Neill is’.[2]

Shane was to his admirers, a defiant Irish lord, who treated the English as equals, to his enemies, both Irish and English, a vainglorious tyrannical ruler, ‘Shane the Proud’ whose ambition in the end caused his own ruin.

A dark legend grew up about Shane O’Neill in his lifetime.

Ciaran Brady begins his recent biography of Shane O’Neill by recounting the hostile legends built up around Shane; that he would ‘swallow up vast quantities of usquebeatha’ (uisce beatha or whiskey)’ and subsequently bury himself up to the neck in hot ash to cure his hangover; that he raped the wife of the O’Donnell chieftain while her husband Calvagh was chained in front of them, that he was cruel but cowardly in battle.

But as Brady points out, all of these stories were spread by O’Neill’s enemies, both Irish and English, after his death. Even his popular nickname, ‘Shane the Proud’ or Sean an Diomais, was an invention of his Irish foes. Burying oneself in ash was a common folk medicine at the time – a cure for arthritis – and Cathleen O’Donnell appears to have willing eloped with Shane and stayed with him until the end. [3]

But outside of those who wanted to praise or damn him, Shane O’Neill was a man of historical significance. He was certainly a cruel man and in modern terms, a ruthless warlord. But more broadly, Shane O’Neill demonstrated to the Tudor English that they would not be able to take control of Ireland and to anglicise it without violence and coercion. The Gaelic political system that spawned Shane O’Neill would not fit into the grooves constructed by the Tudor state in Ireland.


The O’Neills of Tir Eoin


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A map of 16th century lordships in Ireland. Courtesy of Rootsweb.

The O’Neill dynasty dominated all of central Ulster in the early 16th century. Their lordship was Tir Eoin – or Tyrone in English – but it reached far beyond the modern county of that name, in fact incorporating all of modern counties Tyrone, Fermanagh and Derry, and much of modern Armagh as well.

The O’Neills had been the foremost power in the north of Ireland since the 12th century and their castles and tower houses dotted the landscape from Clandeboye in the east to the Foyle river the west.

To the east of the O’Neills’ for most of their history was the Anglo-Norman Earldom of Ulster, held by the de Burgh family but this gradually fell apart in the late 15th century and in their stead, the eastern coast of Ulster had begun to be colonised by the Gaelic Scottish clan, the MacDonnells. To the west, in modern Donegal, the O’Neills were bordered by their perennial enemies and rivals for supremacy in the west Ulster, the O’Donnells. Only force subordinated a host of smaller lordships in Ulster, such as the O’Cahans and O’Reillys to the O’Neills.

Their chieftain was known simply as The O’Neill – like all other Gaelic Irish lord, the ‘head of his name’ – but in reality they were essentially kings of a small independent country in Ulster.

The O’Neills had ruled most of central Ulster since the 12th century but in the 1540s they were first recognised by the English.

Like all Gaelic lordships, the O’Neill lordship was internally unstable. According to Gaelic custom and law the lordship was not automatically inherited by the eldest son (‘primogeniture’ in contemporary English terms), but rather was the subject of fierce competition between a wide pool of cousins and nephews – the derbh fhine or true kin. In theory the successor was elected but in fact many successions were ultimately settled with violence between the rival cliamants and their personal following.  What was more, the losers in such civil wars, disaffected minor chieftains, would often break off from the main clan and set up their own independent lordship, as did the O’Neills of the Fews (modern South Armagh) and Clandeboye.

The O’Neill chieftains had traditionally dealt carefully with the English presence in Ireland,  from whom they were independent, at times fighting with the English authorities in Dublin, but just as often negotiating with them. In any case, its authority, by the 16th century restricted to the Pale around Dublin, only touched the borders of the O’Neill lands in modern County Louth.

However, by the time Shane O’Neill was born in 1530, youngest son of the chieftain Conn Bacach O’Neill, all of this was changing. Under the Tudor monarchs, who were concerned that Ireland could be a source of foreign invasion to England itself, the English embarked on a project to bring all of Ireland under their control.

When, in 1541, King Henry VIII of England declared himself King of Ireland (rather than ‘Lord of Ireland’ as previous English monarchs had) he offered the Irish lords a settlement known as ‘surrender and regrant’. Previously English theory had been that the Gaelic lordships were ‘his majesty’s Irish enemies’ and that a constant state of war existed until they were conquered. But now under ‘surrender and regrant’, Irish Lords such as Conn Bacach O’Neill would swear fealty to the King, recognizing his authority and in return by ‘regranted’ their lands under and English title – in Conn Bacach O’Neill’s case the ‘Earl of Tyrone’.

Civil War in Ulster


Shane O’Neill was the fifth and least favoured son of Conn O’Neill, some even claimed, erroneously, that he was the illegitimate son of a Dundalk blacksmith. But he made his name as a formidable warrior in the 1540s and 50s. When Conn O’Neill was placed under arrest in Dublin in 1551, for raiding the English Pale, Shane took up position as the chief ‘captain’ of the O’Neills, holding the lordship together in the absence of its leader.

A bloody succession dispute broke out among the O’Neills in the 1550s, from which Shane emerged victorious.

Shane had, for a military force, the backing of his foster family the O’Donnellys and successfully hired Scottish mercenaries from among the MacDonnells. However his bitterest enemies were his own kin, and in the 1550s the O’Neill lands descended into a bitter civil war between Shane and his brothers and half brothers. At first, Shane claimed to be acting on behalf of Conn, the Earl, against his rebellious sons who wanted to either split up the lordship of take the title of O’Neill for themselves.

Acting with great ruthlessness, Shane stripped the succession to the Lordship from the English-backed Feardaragh (Fear Dorcha – dark man, also called Matthew) O’Neill whom the English had granted the title of Baron of Dungannon. Shane was the youngest son but he was the strongest war leader. He launched a bloody campaign against his half-brothers and their territory, which he burned and spoiled.

By the time of the bloodletting was over, Shane had emerged victorious. By 1554 he had seen Feardaragh, the English successor killed. Not content with this, he also exiled Conn from the O’Neill lands and on the death of the latter in 1559 in the Pale, Shane had himself made The O’Neill.[4]

This type of internal conflict was not at all uncommon in Gaelic Ireland. Shane was, to Gaelic eyes, the legitimate successor, merely the winner of a bloody and messy succession dispute.  The problem was that the English recognition of one claimant forced them to choose sides.

Enter Sussex

Anthony St Leger, the Lord Deputy entrusted with implementing the advance of the new Kingdom of Ireland, throughout most of the 1540s and 1550s, preferred making allies by conciliation rather than enemies by confrontation. He was also not above giving and taking bribes from local interests to grease the wheels of diplomacy. The Lord Deputy did have run-ins with the O’Neills. In response to their raiding of the Pale, he raided back into Ulster via an aggressive garrison of English troops under Nicholas Bagnal, who were established at Newry in east Ulster.

The Earl of Sussex was determined to enforce the ‘rightful’ O’Neill heir according to English law. A stance that meant war with Shane.

At one point Con O’Neill, the chieftain was arrested when he visited Dublin, by Croft, an interim Lord Deputy. However for St Leger, such conflicts were always temporary and could usually be resolved by compromise. He had O’Neill released.

St Leger stayed in place, on and off, until 1556 before finally being sacked for his pervasive corruption and replaced by the Earl of Sussex.[5]

Sussex was a major English aristocrat  and was, unlike his predecessor, a man with a fixed agenda. He diagnosed that Ireland’s violence was not simply a result of militarised independent lordships, but a result of “faction” – the series of alliances that kept Irish lords constantly in arms against each other – so for instance the alliance between the O’Neills and the Earls of Kildare would have to severed and the O’Neills and O’Donnells forced to make peace, under English backed rulers.

In the case of the O’Neills, he insisted, against the better judgement of some others in the Dublin administration, that Shane, the usurper, in his eyes, should be forcibly removed and replaced by the English backed candidate; Hugh, the surviving son of Feardaragh O’Neill. He also planned to expel the Scottish MacDonnell clan from Ireland altogether. [6]

By all this, Sussex proclaimed he would finally establish the rule of common law throughout Ireland. From the start, Sussex’s theoretical programme proved inadequate when faced with awkward Irish realities.

Shane had built up a large military force of about 4000, partly through mercenaries, but also through pressing his peasant dependants into military service. He raided the Pale incestantly, burning the town of Carlingford and blockading Dundalk. He also took the opportunity to raid the O’Donnell’s territory to punish them for allying with Sussex and it was at this point that he captured their chieftain, Calvagh and took his wife as his own. [7]


Sussex’s campaigns


Sussex led several expeditions into central Ulster to depose Shane and re-introduce what he considered the rightful heir of the O’Neill dynasty (or the Earldom of Tyrone as he saw it). His forces marched from Armagh into O’Neill lands in 1559 and in 1560-61, rounding up cattle and crops but unable to destroy Shane’s powerbase.

Wisely perhaps, Shane did not attempt to confront Sussex in battle, but reverted to the time- honoured Gaelic tactics when faced with a superior force. He denied the enemy the chance to live off the land by removing cattle and crops from their line of march and withdrew to the woods, hills and bogs, from where he harried the flanks and rear of the English columns. As a result, Sussex spent the better part of his expeditions to Ulster marching around searching for an invisible enemy until his supplies or the weather gave out. At this point he would have to return to Dublin, leaving Shane firmly in possession of Tir Eoin and proud as ever.

‘For so long as one son of a Saxon remains in my territory against my will’, Shane O’Neill wrote to Sussex, ‘there will be no peace’.

‘For so long as one son of a Saxon remains in my territory against my will’, he wrote to Sussex, ‘there will be no peace’.[8]

Sussex’s grand programme for pacification thus turned out to be an abject and costly failure. The burden for paying for it fell mainly on the Palesmen, who, disgruntled at the Lord Deputy’s adventures, refused to approve extra taxation in the Dublin parliament. And were instead coerced into paying “Cess” – an extra-parliamentary tax originally intended to pay for the quartering of the Lord Deputy and his bodyguard, but which was reinterpreted to mean paying for the quartering of all Crown troops in Ireland. In the Pale, this imposition was viewed as arbritrary and illegal military government and a boycott was organised throughout the 1560s and ‘70s.[9]

Humiliatingly, for Sussex, while his military strategy was failing, The Earl of Kildare and Sir Thomas Cusack managed to get Shane O’Neill pardoned and invited to Elizabeth I’s Court, where Shane histrionically prostrated himself before the Queen, but then read out a series of demands. At Court, Shane argued that he should be recognised as the legitimate Earl of Tyrone, since Feardaragh had been a bastard son of Con Bacach, and besides, as The O’Neill, Shane was already “the head of his people” by Irish custom. [10]

This was a significant claim on Shane’s part – claiming primacy for the position of The O’Neill, over the inherited title of Earl which the English recognised. Although Elizabeth did not accept O’Neill’s argument, the incompatibility of English and Gaelic social organisations was a worrying omen for the future. Shane returned to Ulster without a settlement, but still in control of Tir Eoin. Unable to curb his further aggression, the English signed a treaty with him at Drumcree in 1563, recognising him as ‘The Lord O’Neill’.[11]

Exasperated and ruined, Sussex was replaced in 1564. His successor, Henry Sidney, inherited his problems.

Shane’s years of triumph and disaster


While the English had made a treaty with Shane O’Neill in 1563, they had no real intention of keeping to it; Shane was becoming too powerful. In 1565 he crushed the MacDonnells at a pitched battle at Glentasie in Antrim, after they had attempted to invade Clandeboye. Over 600 Scots were killed. He also enforced his authority over the Irish lords in Breifne (modern Cavan) and expelled the English garrisons from Newry and Dundrum in what is now County Down. Rumours had also reached the English that Shane was intriguing with Mary Queen of Scots and with the King of France.[12]

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A depiction of the death of Shane O’Neill at the hands of the MacDonnells at Cushendun.

In 1566 Elizabeth formally sanctioned the breaking of the treaty that had been made with Shane in 1563 and the Lord Deputy Henry Sidney again led his forces to war with Shane.

As with Sussex’s expeditions, at first this did not go at all well for the English. Shane besieged the town of Drogheda for a time and an English garrison established at Derry was forced to evacuate by sea.

The downfall of Shane the Proud did not in fact come at English hands at all, but in an amazing stroke of fortune for Henry Sidney and the Dublin administration, at the hands of the O’Neill’s hereditary enemies, the O’Donnells.

Shane was undefeated by the English but was defeated by the O’Donnells and killed by the MacDonnells.

Shane marched his army into their territory in 1567 in order to impose his authority on O’Donnell allies, O’Cahan and O’Hanlon, who had ceased paying O’Neill tribute. In a fierce battle at Farsetmore, near the modern town of Letterkenny, Shane was routed. Out of 2,000 men he brought to the battle, over 1,500 were lost, some in the fighting, many drowned in the River Swilly as they tried to get away.

Having lost the bulk of his fighters, Shane turned to the MacDonnells of Antrim, the allies of his youth, for refuge and reinforcements. The MacDonnells though, keeping in mind Shane’s recent ravaging of their own territory, killed him instead and an English officer William Piers, sent Shane’s pickled head to the Lord Deputy in Dublin, who displayed it on the walls of Dublin Castle. [13]




Sussex, the Lord Deputy who was brought down by his inability to topple Shane, once wrote, ‘if Shane be overthrown all is settled, if Shane settle all is overthrown’. But in fact Shane O’Neill’s death settled nothing at all in Ulster or in Ireland generally.

The MacDonnell’s in the short term received thanks and promises of future accords for killing Shane, but in the 1570s, the English under the Earl of Essex, made a concerted but failed, attempt to remove them from Ireland, in the process carrying out an atrocious massacre of MacDonnell clans-people in 1575 at Rathlin Island. Nevertheless, the MacDonnells held their lands and the campaign was eventually called off on the orders of the Queen. [14]

Turlough Lineach O’Neill, a cousin of Shane’s took over as The O’Neill and unlike his belligerent predecessor, quietly built up alliances with the O’Donnells and MacDonnells, which served to shore up all of their position against the English. His successor in turn, Hugh O’Neill, the one time English protégé, would eventually return to Ulster and wreak a terrible vengeance on the sons of Shane, who had killed his father. But Hugh was no English stooge, in fact he would fight largest Gaelic war of resistance against them – the Nine Years War – in 1594-1603.

Shane O’Neill was, of course, no nationalist hero. He, like all of his contemporaries, lived in a different world, where such categories did not yet apply. He was a self-interested Gaelic lord, who fought his clan rivals and indeed rival O’Neills more than anyone else. But his career does tell us something about sixteenth century Ireland.

The English project of ‘reforming’ Ireland could not happen peacefully. Gaelic and English modes of law and government were too different, too incompatible to be fused peacefully. Only after a great deal more blood had been shed would English rule advance over all of Ulster and all of Ireland.




[1] Thomas Wright, History of Ireland from the earliest times. The quote is from the English historian William Camden, who wrote in the early 17th century.

[2] Eleanor Hull, A History of Ireland,

[3] Ciaran Brady, Shane O’Neill, UCD, 2015, p1-5

[4] Sean Connolly, Contested Ireland, Oxford 2007, p.139-141

[5] Colm Lennon, Sixteenth Century Ireland, the Incomplete Conquest, p174-175

[6] Ibid. p179

[7] Lennon, p268-269

[8] Brady, p143

[9] Lennon p181-182

[10] Ciaran Brady, Shane O’Neill, p38-47

[11] Brady, p.66

[12] Brady, p74-75

[13] Lennon p274

[14] Lennon p274-280

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