Lord of upper Clandeboye until matters took a turn for the worse
A member of a minor branch of the powerful Ulster Gaelic noble family, Conn McBrien O’Neill succeeded his cousin, Sir Conn McNeill Og O’Neill, in the lordship of upper Clandeboye in 1589. The fort of Castlereagh, and territory from Belfast to a few miles from Portaferry, passed into his possession under English law.
However, O’Neill’s relationship with the English forces under Arthur Chichester deteriorated, and in 1601, during a ‘grand debauch’ at Castlereagh, some of O’Neill’s retainers fought English troops from the garrison of nearby Belfast. The fracas, often deprecated as little more than a drunken brawl, may actually have involved more than 350 fighters.
On Chichester’s orders, O’Neill was imprisoned in Carrickfergus castle, although by some accounts he was held under relatively loose arrest with lightly guarded access to the town. His escape was orchestrated by the Scot Hugh Montgomery, Laird of Braidstane in Ayrshire, in return for half of the Clandeboye lands. A well known legend also tells how O’Neill's wife packed ropes for his escape into hollowed out cheeses.
The bargain between O’Neill and Montgomery was approved by the new king James I, although the deal was complicated by the third share claimed by another Scot, James Hamilton.
O’Neill returned to Castlereagh in 1605 but, reputedly because of a taste for high living, he was periodically forced to sell off or lease parts of the remainder of his estate. Debts to Mongomery are mentioned in 1612, with Hamilton leasing further O’Neill lands in 1616. That same year, the castle, town and lands of Castlereagh were sold to Sir Moyses Hill, the founder of the family of the Marquises of Downshire, along with most of O’Neill’s remaining lands.
At the time of his death in 1618, only two of O’Neill’s 224 freehold townlands remained in his hands.
East Belfast: Paintings and Stories from Harbour to Hills (2001) by Keith Haines; Belfast: An Illustrated History (1987) by Jonathan Bardon; Elizabeth’s Irish Wars (1950) by C Falls; Montgomery Manuscripts (1869) edited by G Hill; The Scottish Migration to Ulster in the Reign of James I (1973) by M Perceval-Maxwell.