O'Doherty, Rosa (c.1588–1660), refugee and political activist, was born on the Inishowen Peninsula in northern Co. Donegal, daughter of Sir John O'Doherty (d. 1601) and his first wife, a daughter of Shane O'Neill (qv). Rosa had five siblings, two sisters and three brothers, the oldest being the O'Doherty heir, Sir Cahir (qv). As the eldest daughter of a leading provincial lord, and the granddaughter of Shane, Rosa had significant status and obligations within native Irish society. It is likely, given her later affiliations, that Rosa was educated and reared under Franciscan tutelage. Politically, her father and brother trod warily between the English and native Irish jurisdictions. To consolidate her family's traditional bond with the O'Donnell , particularly after Sir Cahir took an Old English bride, Mary Preston, daughter of Christopher, 4th Viscount Gormanston, Rosa was betrothed to Caffar O'Donnell (qv), brother to Rory (qv), 1st earl of Tyrconnell. In June 1605, she gave birth to her first child, a boy named Hugh. Born with six toes on one foot, he seemed destined to fulfil a prophecy that such an O'Donnell would drive all Englishmen out of Ireland. Sometime after his second birthday his parents took him to the Continent as part of the September 1607 ‘flight of the earls’. Not yet 20, Rosa O'Doherty had to reconcile her life to the uncertain fate of exile.
After a turbulent voyage, the refugees landed in France and were redirected to the Spanish Netherlands. On their way to Brussels, Rosa and the womenfolk were met and escorted by soldiers from the archduke's Irish regiment. Among the officers was Capt. Don Eugenio (Owen Roe) O'Neill , who would later become her second husband. This marriage resulted from a debilitating chain of setbacks that further upset Rosa's unsettled world. It began with the ‘flight’ exiles being directed away from western seaports to Rome. Following this decision, Rosa's infant son was kept in Louvain under the supervision of the Dames Blanches with his cousin, Rory O'Donnell's son. Once in Rome, her husband and her brother-in-law (Rory) succumbed to a fever contracted in the marshland suburbs of Rome. The mournful young widow had few prospects. She was consoled by her late husband's sister, Nuala O'Donnell (qv), who was charged with administering the Tyrconnell subsidy to O'Donnell relatives and dependants.
Initially, Hugh O'Neill (qv), 2nd earl of Tyrone, and the O'Donnell women petitioned the Spanish crown for permission to relocate in the Spanish Netherlands. The women bemoaned the oppressive climate and expressed a desire to look after the well-being of the young O'Donnell heirs. Nuala eventually gained permission to return to the Lowlands, but Rosa's requests were denied. Unwilling to accept this decision, Rosa in June 1612 set out on her own. Spain accepted this fait accompli and transferred her pension of eighty crowns a month to Flanders. Taking up residence with Nuala O'Donnell in Louvain, Rosa reacquainted herself with Tyrone's nephew and Franciscan protégé, Owen Roe O'Neill (qv), the ‘sergeant-major’ (everyday administrative manager) of the Irish regiment serving in Flanders. Their marriage, some time in late 1614, was politically expedient. Within a few years of the marriage, Rosa gave birth to her only surviving child with Owen Roe, a son, known later as Henry Roe. Rosa was now the mother of two boys with politically significant lineages. Her oldest son, Caffar O'Donnell's child, later became a captain in his stepfather's regiment and was killed in 1625 at the siege of Breda.
For the greater part of her marriage, Rosa seconded and represented her husband during his service in the Spanish Netherlands. Her best-documented years were the result of English surveillance preceding the 1641 Irish rebellion. The purchasing of arms, the assembling of shipments for Ireland, and the gathering of intelligence were some of Rosa's identifiable responsibilities. She divulged these actions in a letter of 16 September 1642 that inquired about the wellbeing of her husband who had gone to Ireland.
Her whereabouts after her 1643 return to Ireland depended on Owen Roe's postings or the commercial ventures of his supporters. It was not until 1648 that her activities were again exposed. At this time she was soliciting funds and purchasing war materials. Sometimes, she actually brought in contraband herself by ship. Otherwise, Rosa frequented the port towns of Limerick and Galway. In Galway, she resided with her daughter-in-law, Eleanor Fitzgerald, Henry Roe's wife, and her infant grandson Hugh (b. 1647). Rosa was not with Owen Roe when he became terminally ill in November 1649; by the time she arrived at Cloughoughter castle in Co. Cavan, her husband was dead. Six months later she learned that Henry Roe had been executed after his capture in the debacle at Scariffhollis.
With the collapse of the catholic cause in 1650, Rosa took her grandson and returned to Flanders as a petitioner and supplicant of Spain. Assisted by the internuncio in Flanders, her grandson was given papal protection and was made a page in the house of Pope Innocent X's family. In December 1660 young Hugh became the 6th earl of Tyrone. He also was made a knight of Calatrava and rose to the rank of colonel in the Spanish service before his death in 1673. His grandmother never lived to see these honours. She died 1 November 1660 in Brussels and was buried next to Caffar's son and Nuala O'Donnell in the chapel of the college of Irish Franciscans in Louvain. A Latin inscribed tombstone survives at the college.