O'Connor Faly (Ó Conchobhair Failghe), Brian (d. 1560), lord of Uí Failghe (Offaly), was eldest of the five sons of Cathaoir O'Connor Faly (qv) (1474–1511), lord of Uí Failghe. In 1511 Cathaoir, a hitherto loyal client of Gerald FitzGerald (qv), 8th earl of Kildare, tried to assert his lordship's independence from the earl's regional suzerainty. This attempt ended with Cathaoir's assassination by his cousins, Brian and An Calbhach sons of Tadhg O'Connor Faly, who had the encouragement of Kildare. Brian O'Connor Faly (qv) ruled Uí Failghe with the military support of the Kildares till his death in 1517. He was succeeded by his brother An Calbhach, whose reign proved short as Brian son of Cathaoir was lord of Uí Failghe by 1520.
The circumstances of Brian's accession to the lordship remain unclear. It is uncertain whether he deposed An Calbhach or naturally succeeded his cousin. In June 1520 Brian, with Maolruanaidh O'Carroll (qv) and Conall O'More (qv), raided the Pale. In July they informed Thomas Howard (qv), earl of Surrey, lord lieutenant of Ireland, that they attacked the Pale on the instructions of Gerald FitzGerald (qv), 9th earl of Kildare, and thus implicated the earl in a treasonable act. Brian then cooperated with Surrey through the autumn and early winter 1520, when Surrey probably invested him as lord of Uí Failghe. However, these amicable relations were brief and Brian was again raiding the Pale in 1521. By the close of 1521 he reaffirmed his loyalty to Surrey, and after the lord lieutenant's departure during the winter of 1521–2, Brian remained allied to Surrey's successor Piers Ruadh Butler (qv), the disputed earl of Ormond.
However, on Kildare's return to Ireland (1523) Brian quickly realigned himself with the earl after a brief confrontation. Between 1523 and 1526 this new bond was further strengthened when Brian married Lady Mary FitzGerald, the earl's daughter. In 1525 Brian played a prominent role in Kildare's reconquest of the midlands. As a result of their bitter struggle for supremacy in Ireland and the French intrigues of James FitzGerald (qv), 11th earl of Desmond, both Kildare and Piers Ruadh were called to be examined before the council in England during August 1526. Before his departure for England, Kildare appointed his brother Sir Thomas FitzGerald as his deputy. By autumn 1527 Sir Thomas had been replaced as deputy by Richard Nugent (qv), baron of Delvin, whose appointment sparked widespread disturbances throughout the country by Kildare's supporters. Brian, with Kildare's covert encouragement, was prominent in resisting the new administration. The Dublin government's response was to withhold black rents payable to Geraldine figures, notably Brian and Conn O'Neill (qv). In the winter of 1527–8 Brian invaded the Pale and, in a symbolic gesture, shod his horse upon the hill of Tara. His struggle with Delvin climaxed when he kidnapped the deputy at a parley in Uí Failghe during May 1528, and held him hostage till January 1529. The response of Kildare and Brian's enemies was incisive. Piers Ruadh, now earl of Ossory, returned to Ireland in spring 1528 and (after Delvin's abduction) made a pact with Brian's brother Cathaoir to depose him as lord of Uí Failghe. Brian's position was further weakened by the king's appointment of Piers Ruadh as deputy on 4 August 1528.
These factors conspired to spark a deadly struggle between the clients of Piers Ruadh and Kildare for hegemony of the strategic midland region. Piers Ruadh's strength within the midlands theatre was evidenced by the attendance of Cathaoir O'Connor Faly and Conall O'More, now lord of Laois, at his investiture as deputy (October 1528). Brian was further hindered by Sir Thomas FitzGerald's acceptance of a government pardon early in 1529. Shortly after this, Brian released Delvin and the government resumed its payment of black rent to him. In 1530 Kildare was finally allowed to return to Ireland. He quickly assessed the scale of the inroads of Piers Ruadh's faction into the midlands and determined on a course of recovery by diplomacy and military aggression. Brian and the other midland lords who had remained loyal were richly rewarded by the earl.
However, the 1531 parliament dealt Kildare a devastating blow by revoking his claims to the absentee lands in Carlow, Wicklow, and Kildare. Kildare's difficulties were compounded when Thomas Howard, now duke of Norfolk, leased all his absentee lands within this region to Piers Ruadh in 1531–2. This had the effect of redirecting the struggle between Kildare and Piers Ruadh back into the midlands theatre. In 1532–4 the struggle between the earls centred on the O'Carroll lordship of Éile (Ely), but the killing of Thomas, son of Piers Ruadh, prompted a countrywide intensification. In September 1533 Kildare and Piers Ruadh were summoned by the king to London. Kildare delayed his departure till spring 1534. Before his departure he appointed his able son Thomas FitzGerald (qv) (Silken Thomas) as deputy.
On 11 June 1534 Thomas, believing his father executed, denounced the king before the council at Dublin. Thomas's failure to take Dublin in September 1534 meant that he was subsequently dependent on the military support of the reconciled O'Connor Faly brothers. The rebel position became increasingly untenable when Sir William Skeffington (qv), the deputy lieutenant, captured Maynooth (late March 1535). This was quickly followed by the forced defections of Conall O'More and of Cathaoir O'Connor Faly in April and August 1535 respectively. On 24 August 1535 Brian and Thomas (now 10th earl of Kildare), surrounded by government troops and their Irish allies, surrendered to Lord Leonard Grey (qv).
The fall of the earls of Kildare created a countrywide political vacuum, particularly in Leinster and in the midlands. After his release, Brian attempted to exploit the political instability for his own ends. He managed to banish his mercurial brother Cathaoir from Uí Failghe between 1535 and 1537. In May 1537 Brian's success was reversed by a large-scale government assault led by Grey, now lord deputy. Grey made an example of the Offaly lord by forcing him to flee into Éile and restored the lordship to the grateful Cathaoir. This defeat reduced Brian to desperate straits, but Fearganainm O'Carroll (qv), lord of Éile, and Ó Meachair continued to protect him. The Irish council forwarded plans to London for a solution in Uí Failghe: either Cathaoir could be created a baron and given the lordship, or he could be settled elsewhere and Uí Failghe planted. All these proposals came to naught when Brian regained his lordship by force in November 1537. This, and the looming threat of an O'Connor Faly–Butler alliance, forced Grey to treat with Brian. In March 1538 Brian submitted to Grey, but the struggle between the lord deputy and the Butler faction continued into 1539. Grey's enemies, led by James Butler (qv), 9th earl of Ormond, accused him of being excessively favourable to the former Geraldines and of being under the influence of Brian. These struggles undermined Grey's government and resulted in his recall to England in 1540.
Grey's recall spurred Brian to burn Anglo-Irish settlements within the Pale and prompted a government expedition into Uí Failghe led by Sir William Brereton (qv), who forced him to conclude a truce. However, on Brereton's return to Dublin Brian resumed his attacks, which may be connected to the formation of the Geraldine League. Sir Anthony St Leger (qv), Grey's successor as lord deputy, forced the submission of Brian and the other midland lords in September 1540. The king, following Brian's submission, ordered St Leger to restore Cathaoir to the lordship and demanded Brian's banishment. St Leger balked at this request, arguing that Brian's exile would greatly undermine the new treaties and thus destablise the whole midland region. In November 1540 Brian offered to hold Uí Failghe of the king, with the title ‘baron of Offaly’. He furthermore submitted his feud with Cathaoir to St Leger's judgement. The deputy recommended that Uí Failghe be divided between the two O'Connor Faly brothers. On St Leger's recommendation, Henry VIII pardoned Brian in 1541, but did not issue him a grant of title to Offaly. However, Brian did receive a regrant of Offaly in 1544. In 1545 he again petitioned the king to hold Offaly from the crown and St Leger proposed that Brian be made a life peer. By June 1545 the London government had prepared letters patent for the grant of a viscountcy to Brian.
But in 1546 St Leger was recalled to London to answer charges of misgovernment. The deputy asked Brian to accompany him as a symbol of what could be achieved through tough but humane government. After considering Grey's fate, Brian seemingly assumed that St Leger was destined for the headman's block, and did not travel to London. Late in 1546 he, with his ally and son-in-law Giollapádraig O'More, invaded Co. Kildare. Sir William Brabazon (qv), the acting governor, and Rory O'More (qv), lord of Laois, brought an army into Uí Failghe, devastated it, and forced Brian to flee into Connacht. In December 1546 St Leger returned from England. He still viewed Brian as crucial to the peaceful rule of Uí Failghe; however, garrisons were to be established within the lordship. In summer 1547 Brian was received into the king's peace by the deputy and was granted lands in Dublin for his private usage.
However, the government's policy towards such lordships was becoming more severe. When Brian rebelled again (October 1547), the London government instructed St Leger not to accept his inevitable submission. Brian's rebellion had his brother Cathaoir's support and that of Giollapádraig O'More, now lord of Laois. When Henry VIII died (January 1547), O'Connor Faly's former patron St Leger was again weakened. During 1547 Protector Somerset, the guardian of the minor Edward VI, defeated the court faction that patronised St Leger. In May 1548 St Leger was replaced by Sir Edward Bellingham (qv). By winter 1548 Brian had sustained huge losses and was finally allowed to submit in November; with Giollapádraig O'More, he was brought to England and interned in Marshalsea, where O'More died shortly afterwards. Cathaoir remained in rebellion till his capture and was executed at Dublin in 1549. Bellingham issued pardons to all the remaining O'Connor Faly leaders and embarked on the plantation of Laois and Offaly in November 1550.
In 1551 Brian escaped from his confinement and made his way northwards to the English border with Scotland. He was seemingly captured by the English while in the company of women and returned to jail. When St Leger was reappointed lord deputy (September 1553), Brian's fortunes briefly changed. St Leger granted monies to Mairghréag, Brian's daughter, to go to England and petition Mary I for the release of her father. The queen acceded to Mairghréag's request, and both father and daughter returned to Ireland in 1554. Brian's son Ruaidhrí gave himself as a hostage to the Dublin government in exchange for his father. However, Gerald FitzGerald (qv), 11th earl of Kildare, interfered within the O'Connor Faly polity by his recognition of Donnchadh, another of Brian's sons, as lord sometime in 1554. This upset St Leger's plans. Ruaidhrí was then released, and Brian was returned to imprisonment in Dublin castle in 1554. There he, the last great lord of Uí Failghe, remained till his death. Brian, by his marriage to Lady Mary FitzGerald, left eight recorded sons and two daughters.