The State Papers of Ireland, in the various assessments of the strength of the rebellious Earl 1586 to 1602, state that this territory and the "woodkern race of outlaws" who lived there (the clan McShane) is considered primary to O'Neill, as it was his most secure refuge for cattle, goods, and people, and away from the military might of the English.
The Earl lived with the McShane-O'Neills after the Battle of Kinsale and the fall of Dungannon to Lord Mountjoy on the slopes of Sleive Gallion.
However, with the loss of the Nine Years' War in 1603, Hugh McShane was able to edge out the Earl and became the new Lord of Killetragh and controlling most of the Lordship of Loughinshollin.
However, with the Flight of the Earls and the power vacuum that created, Hugh McShane and the other smaller lords had to deal with the sudden presence of the English military in Ulster.
Conn MacShane held an adjoining portion, and he and Henry both received large estates in Armagh and Fermanagh.
Hugh's new neighbour and friend was the departed Earl's nephew Brian Crossagh, son of Sir Cormac MacBaron O'Neill, something that would cement a friendship impacting them both in later life.
[5] After his pardon in 1608, Hugh slipped back into the forests of Loughinshollin barony and held on to what power he could during the early years of the Plantation of the newly established County Londonderry.
[citation needed] As planters moved into the territories to the north, the combination of the dense forest and Hugh's reputation kept most new arrivals out.
Sir Thomas Phillips tried in vain from the small fort in Desertmartin to subdue the old Chief, but his strength with the McShanes was unmatchable with the local Irish, and he was never captured.
He remained on his former lands, but eventually became known as a highwayman, controlling the forests and roads of southern Londonderry and the GlenShane pass.
In response to this new Protestant army in Ireland, Brian McShane O'Neill took a Royal commission and fought for the King.
Hugh's grandchildren continued to live on the lands Brian eventually settled in the Drapers' portion of Loughinshollin barony, part of his father's old estate.