Confederate Ireland
In 1642, his uncle, Owen Roe O'Neill, organised the return of 300 Irish officers in the Spanish service to Ireland to support the Irish Rebellion of 1641. O'Neill's men became the nucleus of the Ulster army of Confederate Ireland - a de facto independent Irish state. Hugh Dubh was captured early in the war by Scottish Covenanter enemies, but was exchanged back to his own side after the Confederate victory at the Battle of Benburb in 1646. He subsequently rose to prominence after the death of his commander, Owen Roe O'Neill, in 1649.