English/Scottish
Sir Henry Sidney, lord deputy during Shane O’Neill’s time and during the attempted plantations in the 1570s.
Sir Thomas Smith, English civil servant and polymath who organised the failed plantation of north Down in 1572.
Walter Devereux, first earl of Essex, who instigated the failed plantation of south Antrim in 1573.
Sir Thomas Norris and Sir Francis Drake—perpetrated the massacre of all the inhabitants of Rathlin Island in 1574.
Sir John Perrot, lord deputy who authorised division of Clandeboye in 1584 among Gaelic Irish.
Sir Arthur Chichester, governor of Carrickfergus from 1599; chief planter of south Antrim in the early 1600s; lord deputy of Ireland in 1605.
Charles Blount, eighth Baron Mountjoy, lord deputy of Ireland in 1600.
Fynes Morrison, Mountjoy’s secretary, who documented progress of his campaign in Ireland.
Sir Hugh Montgomery, Scottish laird, acquired a third of south Clandeboye and planted it with Scots.
James Hamilton, Scottish spy for James VI & I, acquired a third of south Clandeboye and planted it with Scots.
Irish
Niall Óg O’Neill (d. 1537), son of Niall O’Neill (d. 1512), last chief of all Clandeboye, ancestor of south Clandeboyes.
Brian Faghartach, son of Niall Óg, killed by Shane O’Neill in 1548.
Shane O’Neill (‘the proud’), the O’Neill, killed in 1567.
Sir Brian McPhelim (north Clandeboye), helped in the war against Shane, executed by Essex in 1574.
Hugh McPhelim (d. 1583), brother of Sir Brian, helped in the war against Shane.
Neill McBrian Ertagh (south Clandeboye), promoted to lordship by Essex c. 1575 to succeed Sir Brian McPhelim.
Shane McBrian, awarded three quarters of north Clandeboye centred on Belfast by Perrot in 1584.
Hugh Óg McHugh, awarded a quarter of north Clandeboye centred on Edenduffcarrick, Lough Neagh, by Perrot in 1584. Killed in 1586.
Neill McHugh, succeeded Hugh Óg McHugh.
Con McNeill, awarded all south Clandeboye by Perrot in 1584.
Hugh O’Neill, earl of Tyrone, led Nine Years War and made Clandeboye a subsidiary territory.
Brian MacAirt, organised military contingents in Clandeboye for his uncle, Tyrone.
Con O’Neill, lord of south Clandeboye 1601–19, lost two thirds of his land to Hamilton and Montgomery and sold off the remainder.