Cathal O'Connor Faly

Cathal O’Connor Faly (Cathal Ó Conchobhair Failghe; c. 1540 - October 1596) was an Irish rebel of noble ancestry.

As a young man, O'Connor was a political spy for the Catholics in Great Britain. He became a rebel and killed several high-ranking English soldiers before escaping to Spain in the 1580s, where he joined the Spanish Armada. He was known by the Spanish as Don Carlos or Don Carolo - though he is not to be confused with Don Carlos, Prince of Asturias. He died in a shipwreck on the 2nd Armada.

O'Connor's family were traditionally the Lords of Offaly, though the Crown forfeited the title in 1550 over his father's insubordination. Cathal's claim to the lordship was recognised by the Spanish, but not by the English.

Early life
O’Connor was born about 1540 into the O’Connor family, specifically the O'Connor Faly branch of the Kingdom of Uí Failghe. The suffix Faly (Failghe) is used to distinguish them from other O'Connor families.

His father was Brian O’Connor Faly, Baron Offaly, and his mother was Lady Mary FitzGerald, daughter of the 9th Earl of Kildare. He was a foster-brother of Richard Tyrrell, who went on to command troops at the battle of Kinsale.

Political career
O’Connor was taken to Scotland as a child. In 1560, he accompanied representative Henri Cleutin to France, and appealed to Catholic Englishman Francis Throckmorton to "intercede for his pardon and restoration". On Throckmorton's advice, O'Connor became a spy in the service of Mary, Queen of Scots.

In 1563, he obtained a grant of Castle Brackland and other lands in King's County (now Offaly).

Rebellion
O’Connor was implicated in the Desmond Rebellions, led by James FitzMaurice FitzGerald and the Earl of Desmond.

In response to the Massacre of Mullaghmast led by Francis Cosby and Lord Deputy Henry Sidney, where over 100 Gaelic nobles were killed, the enraged O'Connor "inflicted great devastation on the English, and often vainly attacked them".

In April 1582, he killed Pallas man Donnell McTibbott O'Molloy in a fight, and killed forty-five of his men. O'Connor also burned Sir Edward Harbert's residence in Durrow Abbey, King's County.

Mackworth
In May 1582, O'Connor and his followers ambushed and captured English Captain Henry (or Humphrey) Mackworth. They met Mackworth at Eosbrye, Co. Kildare, where he was returning from Dublin to Philipstown, under the pretence of parleying with him. Instead, the group captured him and carried him off to the woods. Lord Deputy Arthur Grey ordered Henry Warren, sheriff of King's County, to call for Mackworth's release. O'Connor refused, unless his safety could be granted via royal pardon from Elizabeth I. When the administration refused, O'Connor murdered Mackworth.

Philip O'Sullivan Beare gives an account of Mackworth's murder in his Historiae Catholicae Iberniae. According to O'Sullivan Beare, a day was arranged for Mackworth to produce the pardon. On the day, as agreed, he arrived on horseback and O'Connor arrived on foot with his ally Conal MacGeoghegan. During their parley, Mackworth frequently showed the two men a parchment but refused to let them read it. He began to leave, but O'Connor sprang from the high ground, grabbed him around the neck and dragged him off his saddle to the ground. Mackworth put the parchment in his mouth and started to swallow, to stop O'Connor and MacGeoghegan from reading it. The men pried his jaws open with their hands, and upon reading the parchment, O'Connor discovered it was an order from the Queen for Mackworth to capture and kill him. O'Connor and MacGeoghegan killed Mackworth for his deception.

Grey had no alternative but to engage in active warfare against O'Connor. The rebel and his followers dispersed themselves among the wilderness of Kildare to escape Grey's incoming forces; they planned to remain hidden until winter for a better chance of retaliation. Eventually, the majority of O'Connor's men submitted and received pardons. Only O'Connor, who had no chance of a pardon, persisted resisting and eluded every attempt by the garrison at Philipstown to apprehend him.

Spain
O'Connor subsequently fled to Scotland in a pinnace; then, disguised as a sailor, he stowed away on a Scottish vessel to Spain.

He joined the Spanish Armada under the Duke of Parma in the Netherlands. After the Armada's defeat, he returned to Spain. By 1588, he was known as Don Carlos (Carlos being the Spanish variation of Cathal).

Portugal
In 1595, O'Connor was in Lisbon, and he received a pension of thirty crowns per month from Philip II. He claimed the lordship of Offaly, which was recognised by the Spanish, but not by the English.

During this time he regularly corresponded with Hugh O'Neill, Earl of Tyrone, leader of the Irish alliance during the Nine Years' War.

In January 1596, the English Crown received a report that 17 ships were set to take 12,000 Spanish soldiers through St George's Channel to Lambay Island, Ireland. O'Connor and Cornelius O'Mulrian, Bishop of Killaloe, would be on board.

Death
In October 1596, O'Connor embarked the 2nd Spanish Armada at Lisbon with his mother, wife, and children, attempting to sail back to Ireland. A storm occurred off Cape Finisterre, and the vessel - the Sonday - perished in a shipwreck at the port of Corcubión, Galicia. O'Connor and his family drowned. Reports of his death reached the English by November.