Olaf The Black

Óláfr Guðrøðarson, commonly known in English as Olaf the Black, was a mid 13th century sea-king who ruled the Isle of Man (Mann) and parts of the Hebrides. Óláfr was the son of Guðrøðr Óláfsson, King of the Isles, King of Dublin, and his wife Finnguala, granddaughter of Muirchertach Mac Lochlainn, High King of Ireland, King of Cenél nEógain. Óláfr was a younger son of his father; his elder brother Rögnvaldr more than likely had a different mother. According to the Chronicle of Mann, Guðrøðr appointed Óláfr as heir since he had been born "in lawful wedlock". Whether or not this is the case, on Guðrøðr's death in 1187 the Manxmen instead appointed Rögnvaldr as king, as he was a capable adult and Óláfr was a mere child. Rögnvaldr ruled the Crovan dynasty's island-kingdom for almost 40 years, during which time the half-brothers vied for the kingship.

At one point Óláfr, who had been given possession of Lewis, complained to Rögnvaldr that his lands were not enough. Rögnvaldr's response was seize Óláfr and send him to the King of Scots, where he was imprisoned for almost seven years. Upon his release, Óláfr undertook a pilgrimage to Santiago de Compostela, after which the half-brothers were reconciled and Rögnvaldr had Óláfr married to Lauon, the sister of his own wife. Sometime after 1217 this marriage was nullified by Reginald, Bishop of the Isles, who may have been an ally of Óláfr against Rögnvaldr. Óláfr then married Christina, a daughter of the King of Scots' protégé Ferchar, Earl of Ross. The chronicle claims that Rögnvaldr's bitter wife tricked their own son, Guðrøðr, into attempting to kill Óláfr; however, Óláfr narrowly escaped with his life and fled to the protection of his father-in-law on the mainland. Together with a loyal follower, one Páll Bálkason, Óláfr later defeated Guðrøðr on Skye.

In the 1220s Rögnvaldr formed an alliance with Alan, Lord of Galloway, in an attempt to fend off Óláfr. Rögnvaldr married his daughter to one of Alan's sons, and it has been theorised that this son was intended to inherit the island-kingdom. Rögnvaldr's actions enraged the Manxmen and in 1226 they deposed him in favour of Óláfr. Rögnvaldr was later killed battling Óláfr in 1229.

In 1230 Óláfr fled to Norway to seek military assistance against Alan and members of Clann Somairle. The Norwegian king's response was to send a fleet into the Isles under the command of Óspakr Ögmundsson, a member of Clann Somairle. Óspakr was slain early in the campaign, after which Óláfr took control of the fleet and secured himself on Mann. The island-kingdom was divided between him and his mutilated nephew Guðrøðr, with the latter ruling the Hebridean portion and Óláfr ruling Mann itself. Guðrøðr was soon after killed on Lewis, and Óláfr ruled the whole Kingdom of Mann and the Isles peacefully, until his death in 1237. Óláfr's restoration on Mann was seen as a success by the Norwegians, and likely favourably viewed by the Scots as well; since the internal struggle between him and his rivals had been brought to an end. Óláfr was succeeded by his son, Haraldr. In all, three of Óláfr's sons ruled the Crovan dynasty's island-kingdom—the last of which, Magnus Olafsson, was also the last of the dynasty to rule.