Shortly before Michaelmas, 1587, when he was not yet fifteen years old, Aodh Ruadh Ó Domhnaill along with four companions went on board a vessel moored opposite Rathmullen in Lough Swilly, enticed mainly by the promise of wine. But the crew under one Nicholas Skipper of Dublin were decoys posing as merchants who, on instructions from Lord Deputy Sir John Perrot, brought the youths in captivity to Dublin. Aodh Ruadh and three of his companions were then lodged in prison in Dublin Castle. A first attempt at escape was made a little over three years later in January 1591 ending with O’Donnell’s prompt recapture, an event said to have caused widespread gloom among the Irish. But a second attempt a year later was successful. Aodh Ruadh returned to Ulster and, following a brief period of recuperation, was installed in the lordship of Tirconnell in the summer of 1592, in succession to his father who resigned in his favour A celebrated career ensued which was cut short by the defeat at Kinsale and his subsequent premature death at Simancas in September 1602.