John MacAskill was born in 1836, the eldest child of Kenneth MacAskill and Catherine MacLeod of old Ruisgarry. The family moved to 9 Ruisgarry (Gunhill), which his father obtained in 1850, and later to 11/12 Ruisgarry (Quay). John became a cottar on his father's croft, before being passed 11/12  Ruisgarry himself following his father's death in 1875.

John married Marion MacAskill, with whom he was to have ten children, including two sets of twins. Following his death in 1908, the croft was passed to their surviving son Neil.

He has the distinction of a sea-rock named after him.