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Óláfr Guðrøðarson (died 1237)
Óláfr Guðrøðarson (died 1237), also known as Olaf the Black, was a thirteenth-century King of the Isles, and a member of the Crovan dynasty.
He was a son of Guðrøðr Óláfsson, King of the Isles and Fionnghuala Nic Lochlainn.
Óláfr was a younger son of his father; Óláfr's elder brother, Rǫgnvaldr, probably 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, after Guðrøðr's death in 1187 the Islesmen instead appointed Rǫgnvaldr as king, as he was a capable adult and Óláfr was a mere child.
Rǫgnvaldr ruled the island-kingdom for almost forty years, during which time the half-brothers vied for the kingship.
Óláfr appears to have held authority on the island of Lewis and Harris.
At some point, Óláfr appears to have confronted Rǫgnvaldr for a larger stake in the kingdom, after which Rǫgnvaldr had him seized and imprisoned by the King of Scotland.
Upon his release in 1214/1215, Óláfr is stated to have undertaken a pilgrimage to Santiago de Compostela, after which the half-brothers were reconciled, and Rǫgnvaldr had Óláfr married to Lauon, the sister of his own wife.
In what appears to have been a politically motivated maneuver, Óláfr had his marriage nullified by Reginald, Bishop of the Isles, and proceeded to marry Cairistíona, a daughter of Fearchar mac an tSagairt.
Whilst Lauon appears to have been a member of Clann Somhairle, a kindred led by Ruaidhrí mac Raghnaill, a man closely aligned with Rǫgnvaldr and opposed to the Scottish Crown, Cairistíona was the daughter of a rising Scottish magnate.
In 1223, Óláfr's marital actions are stated to have precipitated Rǫgnvaldr's son, Guðrøðr Dond, to attack Óláfr on Lewis and Harris, driving him into Ross to safety of his father-in-law.
Together with Páll Bálkason, Óláfr later defeated Guðrøðr Dond Skye.
The following year, Óláfr confronted Rǫgnvaldr on Mann, and the two partitioned of the kingdom between themselves.
One of Rǫgnvaldr's allied against Óláfr was Alan fitz Roland, Lord of Galloway, who is recorded to have campaigned in the Isles against Óláfr.
There is reason to suspect that Óláfr was conversely aligned with Alan's opponent in Ireland, Hugh de Lacy, Earl of Ulster.
In 1226, Rǫgnvaldr and Alan orchestrated the marriage of a daughter of Rǫgnvaldr to Alan's bastard son, Thomas, a union that led the Islesmen to depose Rǫgnvaldr in favour of Óláfr.
In 1229, Rǫgnvaldr invaded Mann, and was killed in battle against Óláfr.
In 1230, Óláfr was forced from his kingdom to Norway by Alan and members of Clann Somhairle.
In response to this latest bout of warfare in the Isles, Hákon Hákonarson, King of Norway decided to send a royal fleet into the Isles, under the command of Óspakr, an apparent member of Clann Somhairle.
When Óspakr was slain early in the campaign, Óláfr took control of the fleet and secured himself on Mann.
At this point, the kingdom appears to have been partitioned between him and Guðrøðr Dond, with the latter ruling the Hebridean portion and Óláfr ruling Mann itself.
In 1231, after the Norwegian fleet left Isles, Guðrøðr Dond was slain, and Óláfr ruled the whole Kingdom of the Isles peacefully, until his death in 1237.
Óláfr's restoration was seen as a success by the Norwegians, and likely favourably viewed by the Scots as well.
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, Magnús, was also the last of the dynasty to rule.
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Haraldr Óláfsson
Haraldr Óláfsson (born 1223 or 1224; died 1248) was a thirteenth-century King of Mann and the Isles, and a member of the Crovan dynasty.
He was one of several sons of Óláfr Guðrøðarson, King of the Isles, although the identity of his mother is uncertain.
When his father died in 1237, Haraldr succeeded to the kingship as a fourteen-year-old, and held the kingship for about a decade afterwards.
Early in his reign, Haraldr was forced to contend with an apparent coup perpetrated by a kinsman and perhaps an otherwise unknown younger brother.
Following this, Haraldr was then ejected from Mann by envoys of his father's overlord, Hákon Hákonarson, King of Norway, who probably took action against Haraldr because the former had refused to render him homage.
Unable to overcome Hákon's supporters in the Isles, Haraldr eventually submitted to Hákon in Norway, and remained there for about two or three years before being restored in the Isles.
Unlike his immediate royal predecessors, who appear to have favoured the title "rex insularum", Haraldr appears to have preferred "rex mannie et insularum".
Three charters from Haraldr's reign are known, two of which are recorded to have borne a waxen seal, depicting a galley on one side and a lion on the other.
Haraldr reigned during a period of competing claims to overlordship of the Isles by the English, Norwegian, and Scottish Crowns.
Like his father before him, and a younger brother after him, Haraldr was knighted by Henry III, King of England.
The act itself brought Haraldr closer within the orbit of the English Crown.
Late in 1247, however, Haraldr returned to Norway and married Hákon's daughter, Cecilía, and thereby bound himself closer to the Norwegian Crown.
Whilst attempting to return to the Isles in the autumn of 1248, the newly-wed's ship was lost at sea south of Shetland in a tidal race known as Sumburgh Roost.
News of Haraldr's demise appears to have reached Mann by the spring of 1249, whereupon his younger brother, Rǫgnvaldr, succeeded to the kingship.
Haraldr was evidently a popular and capable king who appears to have garnered much of his support from the Hebridean portion of his realm.
His untimely death, however, led to the continuation of the vicious kin-strife which had wracked the Crovan dynasty during his father's floruit.
The chaos brought about by Haraldr's demise appears to have contributed to the invasion of Argyll, and near conquest of the Hebrides, by Alexander II, King of Scotland.

Question: Who is Haraldr Óláfsson's paternal grandfather?