Upon the death of his father in 1513, his mother Dame Margaret Hepburn held the Crown lands of Orkney for nearly thirty years without disturbance or interruption.

Her husband, the 4th Lord, had in about 1489, been appointed one of the commissioners to collect the King's rents in Orkney and Shetland and in 1501 had taken a step towards regaining the Isles by obtaining a lease of the earldom for nineteen years.

In 1514, it is recorded that the 4th Lord, then deceased, had sold to James IV of Scotland eight pieces of artillery for £100 to be paid to his widow.

Together, they gathered a considerable military force and invaded Orkney but were defeated at the Battle of Summerdale where the Earl of Caithness and 500 of his followers were killed.

[1][2] He received a charter for himself and his spouse Elizabeth Keith for the lands of Newburgh, Aberdeenshire and the fishings of the river Ythan on 17 April 1524.