Colonel Shane O'Neill, 3rd Earl of Tyrone (Irish: Seán Ó Néill; Spanish: Juan O'Neill; also anglicised John O'Neill; 28 October 1599 – 29 January 1641) was an Irish-born nobleman, soldier and member of the Spanish nobility who primarily lived and served in continental Europe. He fought for Spain in the Franco-Spanish War (1635–1659) and the Reapers' War.

O'Neill was born during the Nine Years' War in Ireland, the son of Irish confederate leader Hugh O'Neill. Shane O'Neill and his extended family permanently left Ireland in 1607 due to hostility from the English-led government. O'Neill grew up in the Spanish Netherlands. By 1610 he was his father's eldest surviving son, and he eventually moved to Spain to serve in the Spanish army. Though James I of England had attainted his father's title (Earl of Tyrone) in 1614, the Spanish court made O'Neill the third holder of the equivalent Spanish title El Conde de Tyrone. Shane was also de jure 6th Baron Dungannon from 1610 to 1614 by patent of the original earldom.

O'Neill succeeded his elder half-brother Henry as colonel of the original Irish regiment (tercio) in the Netherlands. He was a major supporter of a proposed 1627 Spanish invasion of Ireland. O'Neill professionally clashed with fellow Irish noble-turned-soldier Hugh Albert O'Donnell, Earl of Tyrconnell, even though their fathers had been wartime allies. Following military success at the Siege of Fuenterrabía, O'Neill was appointed a member of the Council of War in 1640. His duties to the Spanish military impeded his lifelong desire to return to Ireland and stage a revolution against English rule. O'Neill died in Catalonia at the Battle of Montjuïc in 1641, and was succeeded by his son Hugo Eugenio O'Neill as both Earl and colonel of the regiment.

Shane O'Neill was born in Dungannon^[4] on 28 October [O.S. 18 October] 1599,^[5] during Ireland's Nine Years' War. His father was Irish lord Hugh O'Neill, Earl of Tyrone,^[6] Chief of the Name of the O'Neill clan, Tír Eoghain's ruling Gaelic Irish noble family.^[7] His mother was Hugh's fourth wife Catherine Magennis, daughter of Sir Hugh Magennis, Baron of Iveagh.^[8] The Magennis family were based in Rathfriland.^[9] Shane O'Neill had two younger full-brothers, Conn Ruadh (born c. 1602) and Brian (born c. 1604).^[10] He also had various elder half-siblings on his father's side, including Conn Mac An Iarla, Rose, Alice, Hugh and Henry.^[11]

From the 1590s to 1603, Hugh led a confederacy of Irish clans against the Tudor conquest of Ireland.^[12] Donough O'Connor Sligo, a loyalist who submitted to the confederacy through intimidation, was made O'Neill's godfather to further enmesh him into the confederacy.^[13] O'Neill was born during a period when the confederacy had won many victories over the English Crown. Catherine was present at Hugh's camp when she was four months pregnant with O'Neill.^[14]

Hugh was repeatedly antagonised by English officials following his surrender in 1603. Possibly facing arrest for a treasonous plot,^[15] in September 1607 he decided to abruptly leave Ireland for continental Europe along with ninety of his followers.^[16] At the time O'Neill was living with Anglo-Irish politician Garret Moore, an ally of his father, and receiving his education alongside Moore's family. On the afternoon of 9 September, Hugh left Moore's house with O'Neill in their preparation to depart Ireland.^[17] On 14 September, at the age of eight, O'Neill left Ireland with his parents during the Flight of the Earls.^[18] His brother Conn was left behind in the rush.^[19] O'Neill's father was accompanied by his wartime ally Rory O'Donnell, patriarch of the comparatively powerful O'Donnell clan of Tyrconnell.^[20] The refugees hoped to reach Spain but were turned away by King Philip III due to fears of violating the Anglo-Spanish peace treaty.^[21] Thus the refugees spent the winter in the Spanish Netherlands.^[22]

In mid-December, the refugees received news that Archduke Albert VII, sovereign of the Spanish Netherlands, wanted them to leave his states.^[23] O'Neill, along with many of the nobles' children, was left in the Spanish Netherlands whilst his parents proceeded to Rome.^[24] He was educated by Franciscans at St Anthony's College, Leuven,^[25] in the company of his brother Brian and fellow nobles Hugh Albert O'Donnell (son of Rory O'Donnell) and Hugh O'Donnell (son of Cathbarr O'Donnell).^[26]

Two of O'Neill's half-brothers died from illnesses in quick succession—Hugh died in Rome in 1609; Henry died in Aranda in 1610.^[27] O'Neill's father Hugh aimed to strengthen Philip III's favour toward O'Neill, now his eldest surviving son.^[28] However, Philip III sought to avoid appearing to side with Irish rebels, which could instigate warfare with England.^[29][b] In 1613, O'Neill went to the court at Brussels as a page to the Infanta Isabella Clara Eugenia, Albert VII's wife and joint sovereign. O'Neill's father continued to compel the Spanish government to grant O'Neill special privileges which could be of use to his exiled countrymen. In September 1614, Hugh sent another petition to Philip III asking him to make O'Neill a Knight of the Military Order of Santiago.^[31] In November, the Infanta wrote in support of O'Neill.^[32] Philip III refused this, stating that other individuals of merit must be attended to first, but that he would consider anything that could be done for O'Neill.^[28]

O'Neill's half-brother Henry had been the colonel of the first Irish regiment in the Spanish army,^[33] known as the "Old Irish Regiment" (Spanish: El Tercio Viejo Irelandés) or "Regiment of Tyrone".^[34] His death left a vacant colonelcy.^[35] The English had previously conspired against the formation of the Irish regiment^[36] and had planted spies there.^[37] Archbishop Florence Conroy feared that the English would try to fill the vacancy with a colonel sympathetic to the English government.^[35] Two weeks after Henry's death, Conroy wrote to Philip III, urging him to immediately appoint Henry's cousin Owen Roe O'Neill to the colonelcy. Hugh instead requested that O'Neill be appointed. Philip III granted this request,^[38] and recommended that Owen Roe should instead be made major of the regiment.^[39] Though Owen Roe had failed in his bid to take command, within a few years of Henry's death he was promoted to sergeant-major of the regiment.^[40] As O'Neill was still pursuing his studies,^[32] Owen Roe served as acting commander until O'Neill was old enough to assume leadership. During his tenure, Owen Roe played a key role in making the regiment into a valuable asset to the Spanish military.^[40]

In 1615, Hugh's chaplain Fr. Chamberlain arrived in Brussels to arrange a marriage between O'Neill and the daughter of Don Juan de Mancicidor (Secretary for War in the Archduke's government). The English representative in Flanders, William Trumbull, warned his government that the marriage would increase the standing of the exiled Irish community. In Trumbull's opinion, "it is high time some underhand means were used to prevent the match". Trumbull was apparently successful; he reported that arguments against the marriage had been put forward, and the marriage did not take place.^[41]

O'Neill's father died in Rome in July 1616.^[42] Though English authorities no longer recognised the title Earl of Tyrone^[3] since it had been attainted in 1614,^[43] the Spanish court granted O'Neill the equivalent Spanish title El Conde de Tyrone.^[c][d] Officially O'Neill was the third of this title.^[44][e] Additionally, O'Neill was de jure 6th Baron Dungannon from 1610 to 1614 by patent of the earldom of Tyrone, though not recognised as such by the Irish House of Lords.^[f]

O'Neill became estranged from his mother Catherine due to arguments over the late Earl's will. They disputed over their shares of the earl's pension as well as the maintenance of his dependents.^[50][51] Hugh's unhappy retainers asked the earl's secretary to inform O'Neill that his mother was refusing to give them the money bequeathed to them. The claimants asked for O'Neill's support and even suggested that Catherine be "enclosed in a convent of nuns". They cautioned O'Neill to send someone to Rome to deposit his father's money and valuables in a bank before his mother could.^[52][53]

In August 1617, O'Neill's 13-year-old brother Brian was found hanged in his room in Brussels with his hands tied behind his back,^[54] possibly killed by an English assassin^[55] or accidentally killed during a children's game.^[56] Despite their arguments over Hugh's will, O'Neill was said to be greatly saddened at Catherine's death in March 1619.^[57] On 9 June 1623, the Infanta Isabella wrote to Philip III's successor Philip IV, requesting that he ask James I of England to have O'Neill restored to his estates.^[58]

Catholic Archbishop Florence Conroy was an important adherent to O'Neill's family during their exile.

O'Neill began his military career in 1615^[32] and assumed command of the "Regiment of Tyrone".^[59][g] Like his cousins and Irish refugees, O'Neill had ambitions to return to Ireland with the regiment to take back his lands and restore his family's rank.^[60] O'Neill used his influence with Pope Urban VIII to have his former tutor Hugh MacCaghwell installed as Archbishop of Armagh and Primate of All Ireland in early 1626.^[61] MacCaghwell died in September that year,^[62] and O'Neill organised the erection of a monument in the Sant'Isidoro a Capo le Case, a Catholic church in Rome.^[61]

Conflict between Spain and England was revived with the Anglo-Spanish War of 1625 to 1630. From 1625, Irishmen living on the Continent pressured the Spanish government to use this conflict to liberate Ireland from English control.^[63] By this time, Hugh Albert O'Donnell had succeeded his father as Earl of Tyrconnell^[64][h] and had begun a military career.^[67] As O'Neill and O'Donnell had claims as the heirs of the two most powerful Ulster clans,^[i] Conroy proposed they take command of an Irish invasion force.^[70] It was agreed that, since "one will never serve under the other",^[71] both men should be made generals of equal footing.^[72] It was also proposed that half of O'Neill's regiment could be assigned to O'Donnell, with Walloon soldiers drafted to supplement the invasion force.^[73] A fleet of 11 ships had been prepared at Dunkirk by March 1627,^[74] with the fleet anticipated to sail in September. Disagreements remained however, as the Spanish government was reticent to be publicly associated with the invasion. O'Neill and O'Donnell also could not abide each other and argued over their roles as joint commanders. The authorities in Brussels wished for O'Neill to be in sole command, while Madrid favoured O'Donnell (probably because Conroy remained there as an advisor).^[75]

With the approval of Philip IV, it was proposed (possibly by Owen Roe) that an Irish republic should be established rather than a new monarchy.^[76] This was to avoid conflict between the earls over who had the right to the throne of Ireland. The Infanta suggested that "the earls should be called Captains General of the said republic and... one could exercise his office on land and the other at sea".^[77] Correspondence within the Irish government demonstrates that O'Neill was considered a threat to English rule. A letter from the Lord Deputy of Ireland, Viscount Falkland, dated 27 April 1627, claimed that O'Neill would have himself crowned King of Ulster by Philip IV. O'Neill would be appointed governor of Ireland on Spain's behalf, and would have the power to create new noble titles, to attract important allies and gain the cooperation of Irish Catholics. Falkland also claimed that a story was circulating among the Irish that O'Neill had already received a crown of gold, which he kept on his bedside table in Brussels.^[61]

Conroy proposed an arranged marriage between O'Neill and Mary Stuart O'Donnell, Hugh Albert's sister, to remove tensions and unify the noble families.^[78] Mary was born in England shortly after the Flight, as her pregnant mother Bridget had been left behind due to time constraints.^[79] Mary was a free spirit and a staunch Catholic who disliked her mother's Protestant family; in 1626 she fled from England following her involvement in a prison break.^[80] She arrived in Brussels in January 1627.^[81] Conroy wrote in March 1627, "Let the king of Spain... get the Infanta to treat of bringing about a marriage between the sister of the earl of Tyrconnell, who has lately fled from England and the earl of Tyrone, and let his Majesty give her a dowry, since her brother cannot do so". O'Neill was then 28; Mary was about 19.^[82] However, Mary was secretly in a relationship with an Irishman named Dudley O'Gallagher, who had accompanied her to the Continent; she rejected the marriage.^[83]

Despite an English expedition on Cádiz in 1625,^[84] the Anglo-Spanish conflict did not develop into full-scale war.^[85] Philip IV was never optimistic about the invasion's chances and was unwilling to support an independent Ireland whilst Spain was officially at peace with England.^[84] Plans for the invasion were abandoned. Conroy died in Madrid in 1629.^[86] Mary became pregnant around this time and her relationship with O'Gallagher was exposed.^[87] The couple fled to Italy in disgrace.^[88]

O'Neill left Brussels for Madrid. Shortly after his arrival in 1630, he submitted two documents to the government: detailed plans for an invasion of Ireland, and a request that the restoration of his family's Irish estates should be included in Anglo-Spanish peace negotiations. Government commissioners felt that circumstances were not yet suitable to grant O'Neill's requests and advised Philip IV to wait for a more favourable occasion. However, it was recommended that the king should placate O'Neill by increasing his pay by two hundred crowns per month. The commissioners were concerned that this pay rise could create a dangerous precedent and make the Irish refugees reliant on the king. It was suggested that, to ensure the stability of the O'Neill family, a marriage should be arranged between O'Neill and some wealthy or noble lady. O'Neill stayed in Madrid for the next three years.^[89]

O'Neill founded the Irish College of St Patrick at Alcalá de Henares in 1630.^[91] O'Neill's confessor, Limerick man Richard Goold, was professor of theology at the College in 1624.^[92] The college closed after O'Neill's death^[93] due to a lack of financial liquidity.^[94]

O'Neill felt slighted and protested when Hugh Albert O'Donnell was given his own Irish regiment in January 1632.^[95] In May 1632, O'Neill was appointed Knight Commander of the military Order of Calatrava.^[96][89]

In January 1635, the French military made efforts to lure O'Neill and O'Donnell to work for their own military.^[97][98] O'Neill sailed from Flanders in early 1638. By June 1638, he was in A Coruña, where he was joined by O'Donnell and his regiment.^[99] The earls' regiments were the first regiments to be transferred from Flanders.^[100] In July, O'Neill and O'Donnell received permission to visit the Spanish court and so they went to Madrid. Prior to O'Neill's arrival at Madrid, Philip IV received a petition from O'Neill to be given "a house suitable for his position, a carriage and maintenance, as he had received the first time he came to the court with the Duque de Ariscot". The Spanish Council of State recommended that this be given as O'Neill's stay would be short.^[99] However, Philip IV recognised the need to not appear to choose favourites between O'Neill and O'Donnell's houses. He wrote: "Examine what can be done with the Count of Tyrconnell considering that both of them are coming to serve in my household; from what my brother has written to me I do not know how the matter may be adjusted evenly.^[101]

O'Neill reached Madrid on 25 July 1638, and wrote to the king: "The weather and the journey have prevented the Count of Tyrconnell and myself from arriving, as we had wished, before to-night. We humbly beg Your Catholic Majesty to compensate for this delay by ordering immediately that we should be employed in your royal service which is the life we most desire in this world".^[102]

When he returned to court in August, O'Neill once again argued that his years of service in the Netherlands warranted greater promotion than he had thus far received. He reminded Philip IV that the O'Neill clan was of royal heritage and deserved to be treated with great honour. However, O'Neill's promotion was delayed as the court was busy dealing with the Franco-Spanish War of 1635 to 1659.^[103] In August, by royal decree, the Earls of Tyrone and Tyrconnell were granted a payment of four thousand escudos for their unpaid service in Flanders, in addition to two thousand escudos from army funds to support their continued service.^[100]

In 1638, the Irish regiments commanded by O'Neill and O'Donnell were transferred from the Army of Flanders to the Basque Country to bolster forces on the northern coast in the face of an expected French invasion. With 1,200 men, the two Irish regiments comprised roughly 10% of the Peninsular force.^[104] A French army of 22,000, led by the Prince of Condé and the Due de la Valette, had begun besieging the Spanish town of Fuenterrabía in July.^[105] A small garrison of five companies had been holding out for two months when a relief force of 12,000 Spanish soldiers reached the town in early September. O'Neill and his regiment were among those in the relief force, and the French were quickly routed.^[103] The two Irish regiments distinguished themselves at Fuenterrabía, significantly contributing to a Spanish victory.^{[106][3][100]}

Following this, O'Neill returned to Madrid. In late September 1638, he submitted another document to Philip IV asking once more for a "house, carriage and maintenance". O'Neill explained that he previously did not press his claims as he was staying in Madrid for only a short time—but with Philip IV's permission he returned to Madrid and left his regiment in Navarre, where they will be better accommodated than they were during his last stay. Three months later, the King informed the Council that there was ample evidence of O'Neill's merits, and it must be decided what favors should be granted to him.^[107]

On 24 May 1639, O'Neill wrote again to Philip IV requesting that he be allowed lead a Spanish army to Ireland.^[108] He wrote:

"In the thirty-two years since my father left Ireland there has never been another occasion like the present for the restoration of Ireland to the Catholics... With four or five thousand men, even with only the Irishmen who are in His Majesty's service here and in Flanders, and arms and munitions for twenty thousand, I shall go in person to accomplish it..."^[109]

The proposal was rejected; on 4 June, the Council of State recommended to the king that "[O'Neill] and his Irish followers must be assured that the protection of Your Majesty will not fail them when the occasion is more favourable".^[108] Philip IV agreed, adding that "the best of all would be not to answer for the present and to continue delaying the matter".^[109]

The Count-Duke of Olivares was highly impressed with the Irish regiments' success at Fuenterrabía, and he sent the regiments to take part in the Siege of Salses in 1640. O'Neill and O'Donnell's participation was decisive in the siege's end. Olivares subsequently boosted attempts to attract Irishmen to the Spanish military. Following the Siege of Salses, O'Neill and O'Donnell's regiments remained in Catalonia for several months.^[110]

In 1640, O'Neill was appointed a member of the Supreme Council of War.^[111] O'Neill's success at the Siege of Fuenterrabía was the main reason for this appointment. This was the first time that an exiled Irishman had held such a high position in the Spanish government, and represented recognition of the work of Irish emigres done in support of Spain.^[112] On 27 April 1640, O'Neill was present at a banquet at the Buen Retiro Palace in Madrid. On 18 August 1640, O'Neill granted financial help to an Irish woman, Sicilia O'Quilli, in his capacity as a member of the Council of War. O'Quilli claimed that her father and two uncles had died in service to the king.^[113]

When the Reapers' War began in 1640,^[114][115] O'Neill and his regiment were sent into Catalonia.^[116] The regiment entered Ulldecona on the night of 27 October 1640, acting loutish and unruly. Ulldecona resident and royal supporter Joan Baptista Giner Martorell described the regiment's conduct in a letter asking for protection from the soldiers: "they have caused some disturbances in the town, notably next to my house... they wanted to tear down the doors, and I have turned them away by giving them wine through the windows..."^[117]

In 1641, the O'Neill and his regiment fought at the Battle of Montjuïc where they suffered heavy casualties.^[106] On the morning of 29 January 1641,^[j] the Catalans made a premature attack^[120] and O'Neill was killed in action near the town of Castelldefels by a musket-ball shot to his chest.^[121] He was among the first to be killed,^[113] and was reportedly "at the head of his men, both he and they fighting with their accustomed valour".^[106] Most of the regiment's soldiers were either killed in battle or taken as prisoners.^[122] O'Donnell, who also fought at the battle, retreated southwards with his own decimated regiment.^[106]

By order of Philip IV, O'Neill's remains were taken to Madrid and buried beside his half-brother Henry in the family vault in the Chapel of the Blessed Sacrament behind the high altar in the Church of Saint Francis.^[123] The contemporary source Commentariiu Rinuccinianus described O'Neill and O'Donnell thus: "Tyrconnell, an accomplished courtier, expert in matters of war, of the greatest courage, but less prudent than Tyrone, a man of singular judgement".^[124] O'Neill was his father's last surviving son.^[2]

Irish rebel Rory O'Moore, unaware of O'Neill's death, sought his assistance for the Irish Rebellion of 1641.^[125] News of O'Neill's death took months to reach O'Moore and caused some confusion among the rebellion's organisers.^[126] It is clear that O'Neill was eager to assist in an Irish rebellion, and would have done so in his lifetime were it not for his obligations in Catalonia.^[127] O'Donnell asked permission for to travel to Ireland, intending to take part in the 1641 rebellion, but this was refused.^[128] He later died in July 1642 in a naval battle off Catalonia.^{[97][129][84]} The earls' deaths in consecutive years were a major blow to Irish expectations that they would lead an Irish rebellion.^[128][84]

During his time in Madrid in the early 1630s, O'Neill became acquainted with Mary and Hugh Albert's cousin Isabel O'Donnell^[84] (Spanish: Doña Ysabel O’Donnell). Isabel, a daughter of Cathal O'Donnell, held comparable standing with O'Neill in the Gaelic nobility.^[130] The couple had a son out of wedlock named Hugo Eugenio (or Hugh Eugene) O'Neill,^[131] who was born in Madrid on 15 November 1633.^[132] A few days before Hugo Eugenio's birth, O'Neill returned to his regiment in the Spanish Netherlands.^[133] Isabel later became a nun in the Convent of La Concepcion Real de Calatrava; she eventually left the convent due to ill health.^[134]

When O'Neill wrote his will on 18 September 1640, he mentioned that he had married the daughter of Madama de Buixln.^[135] Per a request in O'Neill's will,^[136] Philip IV legitimised Hugo Eugenio.^[137] Hugo succeeded his father as colonel of the Irish regiment,^[138] and as "Conde de Tyrone".^[139] It was O'Neill's wish that Gaspar Bernaben, his business agent and friend, should continue to serve and care for Hugo until the boy reached a suitable age, and also that Hugo should learn the Irish language.^[140]

O'Neill also had a daughter named Catalina O'Neill, who was left in Bernaben's care. The identity of Catalina's mother is not stated in O'Neill's will. O'Neill wished for Catalina to become a nun, and he also wished for Catalina to inherit the possessions and money left to Hugo in the event of Hugo's death.^[140]

In his will, O'Neill requested that, if Hugo had no sons, for the earldom to pass to (in order):

1. Conn O'Neill, son of Cormac MacBaron O'Neill
2. Hugh Dubh O'Neill, son of Art Óg O'Neill, son of Art MacBaron O'Neill
3. Owen Roe O'Neill, son of Art MacBaron O'Neill
4. The closest relative of Shane O'Neill the Proud^[141]