 Montgomery's friendship with the king was useful to him next in establishing a Settlement in Ireland in 1606 (preceding the Plantation of Ulster in 1610).Looking for opportunity for advancement, Montgomery came into contact with the wife of Con O'Neill, a landowner in Ulster, who was imprisoned at Carrickfergus Castle for instigating rebellion against the Queen.Montgomery and Ellis O'Neill (the wife) made a deal that the O'Neills would give half of their land to him if he could free Con and secure for him a royal pardon.