The History of Leith

August 23, 2007

Sinclair family (per. 1280–c.1500), nobility

Sinclair family (per. 1280–c.1500), nobility, has a particular importance because of its acquisition of the ancient Norwegian earldom of Orkney in 1379. By the time that the family lost the earldom 100 years later, many individual Sinclair branches had established themselves throughout the Orkney and Shetland islands. The ancient earldom of Caithness (conjoint with the earldom of Orkney from saga times) was not, however, given to the Sinclairs in 1379, but was none the less acquired by the last Sinclair earl in 1455; thereafter many branches of the family similarly sprang up on earldom lands throughout the north mainland of Scotland. This has resulted in the name of Sinclair being one of the most common surnames in northern Scotland and the northern isles today.

Southern origins

The first Sinclairs to be recorded in Scotland were based south of Forth in Midlothian, where the lands and barony of Roslin were granted to Sir William Sinclair on 14 September 1280. Cousland, Roslin, and Pentland were named together as the baronies of the Sinclair family in 1325 but Roslin became the most important seat, and Earl Henry called himself lord of Roslin when granted his Orkney earldom title in the late fourteenth century. It was there that the family’s main fortified residence was constructed above the gorge of the River North Esk. Sir William was active in political life under Alexander III and King John, and he and his sons Sir Henry Sinclair [see under Sinclair, Sir William (d. 1299×1303)] and Bishop William Sinclair all supported Robert I in the wars of Scottish independence. In 1321 Sir Henry appears as royal bailiff in Caithness, a rather surprising move north which anticipates the future role which the Sinclairs were to play in the Scandinavian parts of Scotland. It may have had something to do with his marriage to Alice Fenton, a northern heiress with lands in Ross. He was predeceased by his heir, Sir William Sinclair (d. 1330), who was slain, possibly with his brother John alongside him, in battle at Tebas de Ardales in Granada on 25 March 1330, as they were accompanying Sir James Douglas to Palestine with the heart of Robert I. William’s heir, another William Sinclair (d. after 1358), was a minor at his father’s death. He married Isabella Strathearn, eldest daughter of the second marriage of Malise, earl of Strathearn, Caithness, and Orkney (d. c.1350), whose heir she had been designated in 1344. By 1364 Thomas Sinclair, probably another son of Sir William’s, was called ‘baillie of the king of Norway’ in Kirkwall, when he witnessed a charter of resignation of land to Hugh Ross, with whose family he had come to be closely associated. The Ross family dominated events in the whole north of Scotland, including Orkney, in the 1350s and 1360s, by reason of the vacuum left by the death of Earl Malise c.1350 without a male heir, and it was evidently through Ross patronage, as well as by marriage and inheritance, that the Sinclairs were raised to a position of power in the north.

Settling in the north

Establishing their position in the far north was not a simple matter for the Sinclairs. Earl Malise had had five daughters altogether, from two marriages. The process of dividing his lands among them was a lengthy one, complicated by the differences in inheritance customs in force in Caithness and Orkney. In the former Scottish law prevailed, and though the lands were divided, the title went to the son of Malise’s eldest daughter (from his first marriage), Alexander de Ard. In Orkney the earldom rights, though not the title of earl, were also granted to Alexander de Ard, though Henry Sinclair (d. 1400), as the eldest of Malise’s grandsons from his second marriage, did obtain a share of the lands. However, Alexander’s government was apparently unsatisfactory, and in 1379, following a meeting with Haakon VI (r. 1363–80) at Marstrand in Norway, Sinclair was granted the title of earl of Orkney, as well, probably, as royal lands and rights. A letter survives, issued by the new earl in September 1379, in which he announces that he has promised the Norwegian king not to alienate or pledge any lands or islands of his earldom of Orkney.

The Sinclairs were entering an unfamiliar, essentially Scandinavian, world, but they took on the challenges of their new position with energy and determination. A struggle for power with Malise Sperra, another of Henry Sinclair’s cousins, who had probably been given authority in Shetland by Haakon VI, lasted until 1391, when Malise was killed. Sinclair may have had more widespread ambitions in the north Atlantic. The interpretation of the so-called Zeno narrative, relating the voyages in Atlantic waters of two Venetian sailors in association with a local magnate called Zichmni, who is usually identified with Henry Sinclair, is fraught with difficulties and continues to generate controversy. Yet none of the adventures described is impossible, and it is not unlikely that this ambitious and successful overlord of an island dominion might wish to retrace the steps of his Norse ancestors across the northern seas, even though there is no supporting evidence to confirm either the apparent attempt to dominate the Faeroe Islands, or the supposed discovery of North America.

Although the Zeno narrative gives the clear impression that Zichmni was at enmity with the king of Norway, it is known that Earl Henry was in Norway or Denmark in 1389 to acknowledge Erik of Pomerania’s claim to the Norwegian throne, and there survives a letter of Richard II of England to Queen Margret of Norway (written between February 1389 and April 1391) showing that Henry enjoyed cordial relations with her. This letter refers in particular to Earl Henry’s complaints to Queen Margret of ‘the intolerable and extreme hurt committed against him’ by Richard’s subjects (Perroy, no. 130). The king comments that the same earl and his subjects, together with French and Scots, have notoriously made war against him, and that he does not therefore feel inclined to give the safe conduct to him which Queen Margret is requesting. However, by 1392 Richard had granted a safe conduct to the earl and twenty-four companions to pass through his dominions—presumably to go to Denmark on some royal business. Where exactly the earl had been making war against King Richard is not clear, whether within his own territories or elsewhere, but his reference to attacks against him by English subjects is likely to be connected with fishing disputes in water round the northern isles.

It is this situation of violence in northern waters which was probably responsible for the death of Earl Henry, which is reported in the fifteenth-century ‘Genealogy’ of the earls as having taken place in Orkney, when ‘for the defence of the cuntrie [he] was sclane thair crowellie be his innimiis’ (‘Genealogy’, 81). This may have been the occasion in 1400 when an English fleet landed in the Orkneys, as recorded by Walsingham. The first earl had at least ten children with his wife, Jean, daughter of Walter Haliburton of Dirleton. However, according to the ‘Genealogy’, at his death Henry’s mother, Isabella, ensconced herself in Orkney, outliving all her sisters and their children, and (perhaps in accordance with Norwegian legal custom) succeeding to nearly all their lands. She held these until her grandson succeeded her, about 1416, which might help to explain why the second earl appears to have had very little to do with his northern earldom. It is doubtful whether this Henry Sinclair (c.1375–1420) ever visited his Norwegian overlord to receive a grant of the earldom title, although he used it from the date of his succession to his father.

National politics

Another reason for the second earl’s distancing himself from his Orcadian inheritance must have been his involvement in the affairs of central and southern Scotland, presumably from Roslin, where he probably resided during the 1390s. He fought at Homildon Hill on 14 September 1402, and was one of the numerous prisoners taken by the victorious English, but must have been quickly ransomed. The battle created a power vacuum in Lothian, which Sinclair, thanks both to his landed interests in the region and to his marriage to Egidia Douglas, a granddaughter of Robert II, aspired to fill. He became very close to the court, witnessing important royal charters from August 1404, and in 1405 leading Scottish troops to Berwick in support of the earl of Northumberland, in revolt against Henry IV. He became one of the guardians of Robert III’s young son, Prince James, and was on his way to France with the prince when both were captured by English pirates on 22 March 1406.

Thereafter Sinclair was in and out of custody for some years. But his recorded movements during the decade after 1406 were all southwards; in 1416, for instance, he had a safe conduct with twenty persons to come from and return to Scotland. However, from this same year there is also evidence that he as well as his brother John were becoming more active in the administration of the northern isles, suggesting that their grandmother Isabella died about this time. In a letter of 11 December 1416, Henry Sinclair, styling himself earl of Orkney, appointed his brother-in-law, David Menzies of Weem, to be tutor testamentary of his son and heir, William, and other children, and governor of all the earl’s men, lands, rents, possessions, and goods in Orkney until his heirs attained their majority. Then eighteen months later, on 21 September 1418, John Sinclair received the very important grant of Shetland as a life fief with all royal rights, which made him the foud (royal official, from Danish foged) and provides the first clear evidence that the Sinclair family had acquired control of Shetland. Earl Henry was one of the magnates who died of ‘le qwhew’, possibly whooping cough, recorded by Bower in 1420.

Although the second Earl Henry’s son and heir, William Sinclair, third earl of Orkney and first earl of Caithness (b. after 1407, d. 1480), appears to have been under age for a few years after his father’s death, he was none the less proposed as a hostage for James I in 1421, and received safe conducts in 1423 and 1424. He met James I at Berwick on his return to Scotland in spring 1424, and was one of the assize which condemned the duke of Albany and his sons to death in 1425. By then he had put forward his claim to the earldom of Orkney which had been controlled by the bishop, Thomas Tulloch, for a period since his father’s death, followed by David Menzies. The remarkable ‘Complaint of the people of Orkney’ sent to the queen of Norway in 1425, along with a letter asking that the young earl be appointed their governor, shows clearly that there had been much disturbance in the islands between the followers of David Menzies and of Thomas Sinclair, a member of the earl’s family established in Orkney. William was not, however, formally invested as earl by King Erik until 1434.

By this date Earl William had married Elizabeth Douglas, sister of Archibald Douglas, fifth earl of Douglas (c.1391–1439), and the widow successively of Sir Thomas Stewart (a son of the earl of Mar) and John Stewart, earl of Buchan. A papal dispensation was granted in 1432 licensing them to remain in matrimony. William was involved in protracted legal battles to assure her legal rights in her second husband’s property, and in 1437, just after the murder of James I, she was given a grant of the fruits of the lordship of Garioch, as countess of Buchan and of Orkney. At the time her brother was lieutenant-general of the kingdom; this marriage had brought Earl William into close contact with the royal court, and in 1436 he had been chosen, as admiral of the fleet, to accompany the king’s daughter on her journey to France for her wedding to the dauphin.

Sinclair’s grip on power strengthened during the minority of James II when his relatives the Douglases were in control, nor did it diminish when the king came of age: he acted as steward at the young king’s marriage with Mary of Gueldres in 1449, and in 1454 was appointed chancellor. By this date his wife had died and he had broken with the Douglases. Sinclair was active in the campaign against the Douglas castle of Threave in 1455, and it was to his custody at Roslin that Sir James Hamilton of Cadzow, previously a leading supporter of the Douglases, was entrusted after his submission to James II in the same year. Also in 1455 he was granted the earldom of Caithness, thus succeeding in reuniting the two ancient northern earldoms which had been separated since the death of Earl Malise c.1350: it was made in compensation for the lordship of Nithsdale, to which he had a claim through his mother, Egidia Douglas. His southern seat at Roslin was also being developed in a manner commensurate with the standing of a magnate of Earl William’s importance. The remarkable church of St Matthew, probably begun in 1446, and given a collegiate constitution in the early 1450s, though never completed beyond the chancel, bears witness through its exotic and elaborate carved stonework to the wealth and taste of its founder. Roslin itself was erected into a burgh of barony in 1456.

The loss of Orkney

From this position of power in the kingdom of Scotland, Earl William’s star waned rapidly. He ceased to be chancellor in the later months of 1456, and along with Bishop James Kennedy moved to the sidelines as the young James II took a more aggressive line in both internal and external politics. In foreign matters the question of the ‘annual’ of Norway (the tribute payable by the Scots since 1266 in return for the cession by Norway of the Scottish Western Isles) loomed large, and inevitably meant strained relations with the king of Denmark–Norway (who should have been Earl William’s acknowledged overlord for his earldom of Orkney, but there is no evidence that he had gone to do homage since 1434, although he had been summoned in 1446). Negotiations over the ‘annual’ took place in the late 1450s, and at a meeting of Danish and Scottish envoys in Paris in 1460 it became clear that James aspired to take control of Orkney and Shetland. Earl William, who must have been aware of royal ambitions regarding his earldom, may have attempted to implement delaying tactics. He certainly embarked on an expensive policy of purchasing ‘odal’ lands (that is, lands not held of any superior lord) in Orkney at this time, apparently with the intention of acquiring an estate which could not be encroached upon by the king. The death of James II in 1460 allowed the earl a breathing space to prepare himself better for the time when royal ambitions would once again focus on his rich northern possessions. Once more he was called upon to guide the kingdom in a period of difficulty, and he acted as one of the seven regents for the minority of James III, which provided him with an excuse for not answering a summons from King Christian (r. 1448–81) to attend the Danish court.

With the rise of the Boyds to power in 1466, Earl William faced once more the prospect of aggressive policies directed by the crown towards the northern isles. The situation of tension over the ‘annual’ was used as a means to achieve royal ambitions, in the marriage negotiations which were conducted at Copenhagen in the summer of 1468. The earl refused all attempts by King Christian to summon him, undoubtedly realizing that his position as vassal of both kings made it exceedingly difficult for him to be involved in the negotiations. These resulted in the extraordinary acquiescence by King Christian in the demands of the Scottish envoys that Orkney be handed over as part of the dowry of the young Princess Margaret. Desperately short of cash, and desperate for a good marriage for his daughter, he agreed to pledge the islands as part payment for the dowry; in the following year he agreed to pledge Shetland for most of the rest. There is little doubt that his transfer included all of the islands, and not just the royal estates. It remained for the ambitious councillors of James III to prevail upon the earl to give up all his rights in his earldom, which he did in 1470, thus ensuring permanent possessions for the Scottish crown in the islands, even if the Danish monarchy should ever succeed in redeeming them. The impression that the earl came out very badly from the ‘excambion’ of 1470 is probably unjustified, since in exchange for his right in the earldom he received the very fine royal castle of Ravenscraig in Fife, a number of valuable privileges and confirmations which he must himself have stipulated, and a handsome annual pension of 400 merks.

Family settlements

From 1470 Earl William was known as earl of Caithness until 1476, when he resigned his earldom in favour of William, the eldest son of his second marriage; thereafter he was only Lord Sinclair. His latter years were occupied with family affairs, although he was named as an envoy to England once or twice. Family matters were problematical, although his second marriage, to Marjory Sutherland, the (possibly illegitimate) daughter of Alexander Sutherland of Dunbeath, was apparently very successful—at least there were fourteen children of it. Alexander Sutherland’s will, dated 1456, may indicate that Earl William’s liaison with Marjory had not at that time been regularized, although it later was. Such a marriage, to a daughter of a member of the Sutherland family with no standing in the north, is very surprising. However, Alexander’s will indicates that he had been a source of credit for the earl, perhaps to help with the land-purchasing policy in Orkney. The children of this marriage clearly took precedence over Earl William’s son of his first marriage, William the Waster, who was not considered suitable to be his father’s main heir, although he did succeed in getting possession of the Fife estates after his father’s death.

In 1476 the old earl did his best to ensure that his main estates went to the elder sons of his second marriage, the earldom of Caithness to William, Roslin and Ravenscraig to Oliver. None the less, shortly after his death, in the early months of 1480, there was serious conflict between the half-brothers, attested by several bonds and agreements. A verdict of idiotry was procured against the elder William in 1482, but the latter’s interests were well represented by his own eldest son, Henry, who eventually restored the fortunes of the family in the northern isles, based on the ‘conquest’ estates which were acquired by the last earl of Orkney, and which did not escheat to the crown along with the earldom lands. He achieved this in conjunction with his uncle, Sir David Sinclair of Sumburgh, an illegitimate son of the old earl who pursued a successful career in the service of both the kings of Scots and of Norway, and who built up a personal estate based on the conquest lands in Shetland, which he prevailed upon all his half-brothers and -sisters to resign to him in 1498. The old earl’s foresight had ensured the survival of a large and powerful Sinclair presence in Orkney and Shetland, as well as in Caithness.


Sources B. E. Crawford, ‘The earls of Orkney–Caithness and their relations with Norway and Scotland, 1158–1470’, PhD diss., U. St Andr., 1971 · Scots peerage, vols. 6–7 · GEC, Peerage, new edn, vol. 10 · R. St Clair, The Saint-Clairs of the Isles (Auckland, 1898) · ‘Genealogy of the earls’, The Bannatyne miscellany, ed. D. Laing, 3, Bannatyne Club, 19b (1855), 63–85 · B. E. Crawford, ‘William Sinclair, earl of Orkney, and his family: a study in the politics of survival’, Essays on the nobility of medieval Scotland, ed. K. J. Stringer (1985), 232–51 · J. S. Clouston, ed., Records of the earldom of Orkney, Scottish History Society, 2nd ser., 7 (1914) · R. H. Major, ed., ‘The voyages of the Venetian brothers Nicolo and Antonio Zeno’, Hakluyt Society, 1st ser., 1 (1873) · University of Guelph, Ontario, Library Archival Collections, Campbell of Menzie papers · Norges Gamle Love, anden raekke, 1: 1388–1447 (1912) [Denrets Historiske Kommissjon, Christiania] · B. E. Crawford, ‘The pawning of Orkney and Shetland: a reconsideration of the events of 1460–69’, SHR, 48 (1969), 35–53 · The diplomatic correspondence of Richard II, ed. E. Perroy, CS, 3rd ser., 48 (1933) · R. A. Hay, Genealogie of the Sainteclaires of Rosslyn (1835) · W. Bower, Scotichronicon, ed. D. E. R. Watt and others, new edn, 9 vols. (1987–98), vol. 8 · G. Burnett and others, eds., The exchequer rolls of Scotland, 9 (1886) · C. Innes, ed., Registrum S. Marie de Neubotle, Bannatyne Club, 89 (1849) · S. I. Boardman, The early Stewart kings: Robert II and Robert III, 1371–1406 (1996) · B. Smith, ‘Earl Henry Sinclair’s fictitious trip to America’, New Orkney Antiquarian Journal, 2 (2002), 3–18

Archives NA Scot., Cookston writs · NA Scot., GD 164 · Wemyss Castle, Fife, Wemyss family papers

by Barbara E. Crawford

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