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Born about 1346 - married

  1. [Florentia, Princess of Denmark]
  2. Jean, daughter of the Lord of Dirleton.

NORWAY: 1343 Hakon VI; 1380 Olaf; 1389 Margaret
SWEDEN: 1364 Albert; 1389 Margaret
DENMARK: 1376 Olaf IV; 1387 Margaret
SCOTLAND: 1371 Robert II; 1390, Robert III
ROME: 1378 Urban VI; 1389 Boniface XI
AVIGNON: 1378 Clement VII; 1394 Benedict XIII

1328 William IV; 1382 William V;1394 Henry; 1397 John - [See Historiettes]

[From Orkneyinga Saga and Barry]

Since the termination of the administration of Alexander de Ard as Governor and Commissioner of the Isles on St.John's Day 1376, the earldom remained for three years in commission. But in the summer of 1379 Alexander de Ard, titular Earl of Caithness, Henry Saint-Clair, Lord of Roslin, and Malise Sperra, Lord of Skaldale, [Skelda in Birsra], the three cousins, competitors for the earldom, passed over to Norway to prefer their respective claims to the Norwegian king, and the result was that at Marstrand, on the 2nd August of that year, Henry Saint-Clair received from King Hakon formal investiture of the Earldom of Orkney, and also of the Lordship of Shetland, which appanage, since the time of its forfeiture to King Sverre by Earl Harald - first of the Atholl line - had been in possession of the crown of Norway.

The conditions on which Earl Henry accepted the earldom are set forth in the Deed of Investiture, and, contrasting them with the semi-independence of the ancient earls, it would at first sight appear as if little more were left him than the lands of his fathers. For, although the Earls of Orkney had precedence over all the titled nobility of Norway, and their signatures to the national documents stand always next after the archbishop's, and before the bishops' and nobles'; though the title was the only hereditary one permitted in Norway to a subject not of the blood-royal, yet it was now declared to be subject to the royal option of investiture. The Earl was to govern the Isles and enjoy their revenues during the king's pleasure, but he was taken bound to serve the king beyond the confines of the earldom with a hundred men fully equipped, when called upon by the king's message; he was to build no castle or place of strength in the Islands, nor make war, enter into any agreement with the bishop, sell or impignorate [mortgage] any of his rights without the king's express consent; and, moreover, he was to be answerable for his whole administration to the king's court at Bergen. At his death the Earldom and all the Isles were to revert to the King of Norway or his heirs, and if the Earl left sons, they could not succeed to their father's dignity and possessions without the royal investiture.

The reversal concerning Orkney not being found sufficient by King Hakon, the ambassadors were allowed to stay in the city of Tunsberg, in Norway, till His Majesty was satisfied. In the meantime there was a marriage concluded, as is said, betwixt John Saint-Clair, brother to the Earl, and Ingeberg, natural daughter of Waldemar, King of Denmark, by Jova Little, who was a daughter of Sir John Little, Commissioner of Rugen. [from Hay's Genealogie]

At the following Martinmas Earl Henry was taken bound to pay to the King 1,000 English nobles (about £333 sterling). It was also part of the compact that Malise Sperra, son of Guttorm Sperra, should depart from all his claims to the Earldom in right of his mother; and the Earl left with King Hakon as hostages for the due fulfilment of his share of the contract the following from among his friends and retinue:- William Dalziel, knight, Malise Sperra, and David Crichton.

King Hakon died the next year, 1380, the year following the investiture of the Earl and the events that took place in the Orkneys during the reign of his successor, King Olaf, are entirely unknown to the Norwegian chroniclers.

The Earl seems neither to have courted the favour of his suzerain, nor to have stood in awe of his interference. Without waiting for the royal consent, and in defiance of the prohibition contained in the Deed of Investiture, he forthwith built the Castle of Kirkwall, from which be seems to have thought himself sufficiently independent to regally rule his sea-girt earldom according to his own will and pleasure. This fortress, in later times called "the King's Castle", was constructed with such strength and skill that the witch-haunted mind of the 17th century believed that only the Arch-fiend himself could have been its engineer and architect. [See Balfour's Memorial and letter Earl of Caithness from Kirkwall, 7th October 1614 in Caithness Events]

From the fact that King Hakon's investiture of Earl Henry took him bound not to enter into any league with the bishop, nor to establish any friendship with him without the kings consent, we infer that the bishop - William IV - was then acting in opposition to the king and to the representatives of civil power. The likelihood is that Earl Henry found this episcopal opposition favourable to his own design of making himself practically independent, and represented it as the excuse for the erection of the Castle of Kirkwall, contrary to the terms of his agreement with the Crown. Munch attributes the discord to the growing dislike of the Norwegian inhabitants of the Isles to the Scotsmen, whose numbers, through the influence of the family connections of the later earls, had long been increasing. Whatever may have been the origin, the end of it was that, in some popular commotions of which we have no account, the bishop was slain, in the year of grace, 1382.

Earl Henry, after establishing himself in the Isles, turned his attention towards rewarding the cadets of his House, as appears from an evident, whereby he obliges himself to infeft his beloved cousin, Sir James St.Clair, Baron of Lougformacus, in a twenty merkland. The words of the obligation run: "Universis patent, etc, Nos. Henricum de Sancto Claro, Comitem Orcadice et Dominum de Roslyn teneri firmiter, et fideliter obligari carissimo consanguineo nostra, Jacobo de Sancto Claro, Domino de Longfurdmakhuse, etc.," which evident is dated at Roslin, the 22nd June 1384. The witnesses are Thomas Erskine of Dun, George Abernethy of Soulis, Walter Halyburton of that Ilk [of Halyburton], and John Halyburton of Dirleton. [From Nisbet's Heraldry]

At Edinburgh, on the 8th November 1387, Malise Sper, Dominus de Skuldale, agrees with the Earl anent the harm that had been done to him and his tenants as is evidenced by instrument of that date. [from Hay's Genealogie]

The next year 1388, is memorable as being the date of Otterburn, The Earl was not present himself, but his kin took a prominent part in it. Tytler has: "At Otterburn, along with the Earl of Douglas, were the Earls of March and Moray, Sir James Lindsay, Sir Alexander Ramsay, and Sir John St.Clair, three soldiers of great experience, and others". Froissart narrates: - "Upon James, Earl of Douglas, being struck down, he continued with his latest breath to encourage his comrades. Sir John St.Clair, his cousin, having asked him "how he did", "Right well", quoth the earl, "but thanked be god there have been but a few of my ancestors that have died in their beds. But cousin, I require you think to revenge me, for I reckon myself but dead, for my heart feinteth oftentimes. My cousin Walter and you, I pray you raise up again my banner which lies on the ground, and my Squire Davy slain; but, sirs, show neither to friend nor foe what case ye see me in, for if my enemies knew it they would rejoice, and our friends be discomfited". The two Saint Clairs and Sir James Lindsay, who was with them, did as they were desired, raised up his banner, and shouted his war-cry of "Douglas". The remainder of the battle was beyond the life of Douglas, for he was dead before it ended, and what was a prophecy in the dying man's mouth became a saying that "the victory was won by a dead man;" and Sir John Sinclair bore the banner.

While these stirring events were occurring in Scotland the Earl was attending to his high offices in Norway, for in 1388 he is present as a Councillor of State, and signs next after the Archbishop Vinoldus in acknowledging Eric of Pomerania as true heir to the realm of Norway. Again, in September 1389, both Earl Henry and his cousin, Sir Malise Spar, are among those present on the occasion of the accession of King Eric of Pomerania.

NOTE - Henry Earl of Orkney and Malise Spar were both present at the Norwegian State Council Meeting at Helsingborg, in June 1389, when Erik the Pomeranian was proclaimed heir to Norway. The transactions are recorded in two documents, the one in Swedish containing signatures, and seals of 20 Councillors including the signature of Malise Spar, but it does not occur in the Latin copy which only contains 19 seals and signatures. Perhaps he was slain before he had time to sign the latter.

The "Iceland Annals", under date 1389, have the following entry: - "Malise Sperra, with seven others, slain in Shetland by the Earl of Orkney. He had previously been taken prisoner by him. From that conflict there escaped a man servant who, with six men, got safely away to Norway in a sixareen" [a six-oared boat].

Malise appears to have endeavoured to establish himself in Shetland in opposition to the Earl. He had seized, it is not stated on what grounds, the possession in Shetland which had belonged to Herdis Thorvaldsdatter, and of which John and Sigurd Hafthorsson were the lawful heirs. It seems as if the Earl was about to hold a court to settle the legal rights of the parties concerned. The court would be held at the old Thingstead near Scalloway, but a conflict taking place, the dispute was terminated by the strong hand, and Malise Sperra was slain. The monolith of grey granite close to the roadside between the Lochs of Tingwall and Asta probably marks the spot where he fell.

In the "Scottish Chamberlain Rolls" of 1438 there is an entry of a receipt of £9 from James Mcfersane for the land formerly belonging to Malise Speir, knight, in the sheriffdom of Banff, remaining in the king's hands. A number of his men having been slain with him, it is probable he was the aggressor, and as both he and the Earl attended at King Eric's coronation in 1389, it is likely the Earl landed in Shetland on his way home from Norway for the express purpose of seeing justice done in the cause of the heirs of Herdis.

Early in 1390 Nicolo Zeno, a Venetian nobleman, was wrecked in a storm on the Faroes, and he and his companions were rescued from the wreckers by the Orcadian Earl, Henry St.Clair, who happened to be in the vicinity with an armed retinue. Accosting the Venetians in Latin, he assured them of his protection, and took Nicolo into his service. The Earl had presumably given chase as far as the Faroes to the adherents of his cousin, Sir Malise Speir of Skuldale, and the first exploit in which Nicolo participated was the reduction of that archipelago. This was accomplished with a fleet of thirteen vessels, whereof two only were rowed with oars - the rest were small barks and one ship. As Nicolo greatly contributed towards the skilful navigation of the fleet through the dangerous channels of the various islands, the Earl, in recognition of his services, administered the accolade conferring on him the honour of knighthood, and he thereafter appears designated in the annals of his country as Sir Nicolo the Chevalier". [Voyages of the Zeni]

Sir Nicolo now wrote to his brother Antonio at Venice, relating his adventurous experiences, and asking him to join him and bring a vessel. Antonio did as desired, and both brothers won much favour with the Earl.

King Richard II of England gave a safe conduct, or passport, to Henry, Earl of Orkney and Lord of Roslin from 10th March 1391-2 to Michaelmas, with permission to be accompanied by twenty-four persons, the necessary persons, etc., with proviso, that no one fugitive from the English laws should be of the company. The king signed it at Leeds Castle, Kent.

By deed executed at Kirkwall on the 23rd April 1391 (and subsequently confirmed by King Robert III), the Earl dispones the lands of Newburgh and Auchdale, in Aberdeenshire, to his brother David de Sanclo Claro for his services rendered and in exchange for any rights he may have to lands in Orkney and Shetland, derived from his mother Isabella St.Clair. Witnesses: Lord Walter de Bochane, Archdeacon of Shetland; Lord Simon de Papay; Lord Thomas de Kirknes; Lord John Punkyne; Lord Michael de Westray; Lord hauquo, militibus; Richard de St.Clair; Thomas de Laysk; Alexander de Claphame; Thomas de Leth, etc.

NOTE - Alexander de Claphame, at Kirkwall, 1391. King Erik the Pomeranian at Lund, 15th April 1412, grants to his trusty servant, Alexander van Klapam, all his lands in North Maven, in Shetland - "Alt vaart godz sem ligger uppa Hieltland for Nordan Mawed huiliket plaeger att skyllda ok gifua tin loduga marker til skat Iandskyld ok wesel," etc. [Diplomaticum Norvegicum]

The Earl, to gratify Sir Nicolo Zeno, and also because he knew full well his value, made him commander of his navy (armada). In that capacity Sir Nicolo with his brother Antonio accompanied the Earl to the Shetlands, and established order in that group; after which the Earl built a fort in Bressay, where he left Sir Nicolo with some small vessels, and men and stores, and thinking he had done enough for the present, returned with the rest of the squadron to the capital of his archipelagic dominions.

Being left behind in Bressay, Sir Nicolo determined the next season to make an excursion with the view of discovering land. Accordingly, in the month of July 1394, he fitted out three small barks, and sailing towards the North, arrived in Greenland, where he stayed some little while observing the manners and customs in those parts. At length, not being accustomed to such severe cold, he fell ill, and a little while after he returned to the Orcades, where he died, a victim to the rigorous climate of the northern regions. [Voyages of the Zeni]

The next appearance of the Earl is at Roslin on the 13th May 1396, when Sir John de Drummond of Cargyll (brother of Annabella, queen of Robert III of Scotland) and his wife Elizabeth make renunciation by deed for them and their heirs in favour of Henry, Earl of Orkney, Lord Roslyn, "patri nostro," and his issue male in respect of claims to the Earl's lands "infra regnum Norvagie".

By charter at Edinburgh on the 24th January 1404, King Robert the Third of Scotland freed the Earl of the Castle Guard due for his Baronies of Rosline, Pentland, Pentland Moor, Colsland, Merton, and Mertonehall, all in the viscounty or sheriffship of Edinburgh. In this charter the Earl is described only as Earl of Orkney, no other title being specified. [Roslyn Chartulary]

On the death of Sir Nicolo Zeno, his brother Antonio succeeded him in his wealth and honours, but although he strove hard in various ways, and begged and prayed most earnestly, be could never obtain permission to return to Venice, for the Earl, being a man of great enterprise and daring, bad determined to make himself supreme in the Northern seas. The Islesmen were then greatly excited by the strange tales of an Orcadian castaway who had returned from the far West after an absence of twenty-six years, and the Earl was inspired with the project of bringing under his sway the rich and populous lands reported in those distant parts. For that purpose he resolved to equip a fleet on a voyage of discovery and conquest. Setting sail with a considerable number of barks and rowboats, and men, he disappointed Antonio Zeno of the chief command.

At the start adverse weather was experienced, and they were unwillingly compelled to circumnavigate Ireland before proceeding on their course, and they eventually reached Greenland, but as the voyage had occupied so long a time their stay was of brief duration. Antonio, in writing to his brother, the famous Carlo, Saviour of Venice,refers to the exploits of St.Clair, "a prince as worthy of immortal memory as any that ever lived, and to the discovery of Greenland on both sides and the city that he founded". [Voyages of the Zeni]

Antonio Zeno returned to Veuice in 1404, for it is stated that he remained ten years in the service of the Earl after the death of Sir Nicolo, which happened late in 1394 or early in 1395. It is known that Antonio died in Venice before 1406, and Michaud dates his death as in 1405. It will be observed that the date of Antonio's return coincides with that assigned for the death of the Earl, viz. 1404, the latter event operating to release Antonio, who immediately availed himself of the position.

The panegyrist [Van Bassan, a fabulous genealogist] of the St.Clairs of Roslin writes of Earl Henry as follows:"After the death of Sir William Sinclair, succeeded to him his eldest son, Henry, Prince of Orkney, Lord Shetland, Lord Saintclair, Lord Chief-Justice of Scotland, Admiral of the Seas, Baron of Roslin, Baron of Pentland Moore (in free forestry), Baron of Cousland, Baron of Cardain Saintclair, and Great Protector, Keeper, and Defender of the Prince of Scotland, who married Elisabeth, daughter to Malesius, Prince of Orkney, Earl of Caithness and Stratherne, through which marriage he became Prince of Orkney, and was more honoured than any of his ancestres, for he had power to cause stamp coin within his dominions, to make laws, to remitt crimes; he had his sword of honour carried before him wheresoever he went; he had a crown in his arms, bore a crown on his head when he constituted laws, and, in a word, was subject to none, save only he held his lands of the King of Noraway, Sweden, and Denmark, and entered with them, to whom also it did belong to crown any of those three kings, so that in all those parts he was esteemed a second person next to the king. He built the Castle of Kirkwell, in Orkney, and proved valiant in all his doings. When Robert II, the first of the Stewarts, succeeded to the Scottish crown, he no less entirely loved the Prince of Orkney than did his uncle, King David, and in testimony of his love to him, he made him Protector and Keeper of the Prince, his son, John Stewart, Earl of Carrick, because he was both the most noble and trustiest in his realm, as writing yet records; and in the 19th year of his reign he died (1389). Henry Sainclaire, having the Prince in his keeping, was advertised of an army of Southrons that came to invade the Orkney Isles, who, resisting them with his forces, through his too great negligence and contempt of his unfriendly forces, he was left breathless by blows battered so fast upon him that no man was able to resist, and left two sons, Henry his successor, and John (hereafter Foud of the Orcadian secundogeniture of Shetland), and nine daughters, who were married thus: -

  1. Beatrix upon the Earl of Douglas (James the Gross, Lord Balveny, 1409, Earl of Avondale, 1437, 7th Earl of Douglas, 1440);
  2. the second upon the Laird of Dalhousie;
  3. the third on the Laird of Calder, named Sandilands;
  4. Jean upon the Laird of Corstorphine, named (Sir John) Forrester (ancestor to Lord Forrester);
  5. the fifth upon the Earl of Errol, named Hay;
  6. the sixth upon the Laird of Drummelzier, named Tweedie;
  7. the seventh upon the Laird of Stirling, named Cockburne:
  8. the eighth upon the Laird of Moreton, named Heron;
  9. Mary upon the Lord Sommerville, so named (Thomas Somerville, of Carnwath, ancestor to Lord Somerville).

NOTE - The right to coin money was never exercised by any of the Orcadian Earls, nor can any Orcadian coins be found in the numismatic collections of Scandinavia.

In the Diploma Earl Henry is stated to have married Janet, daughter of Walter Halyburton of Dirleton, by whom he had Henry II, his successor. In an attestation dated 1422, by the Lawman and Canons of Orkney, of the descent and good name of James of Cragy, Laird of Hupe, it is expressly certified that Henry St.Clair was himself married to a daughter of the younger Malise, styled "ELIZABETH de Stratherne, daughter of the late reverend and venerable Malise, Earl of Orkney", and that by her he had a daughter, Margaret, who was married to James of Cragy. Patrick, 13th Bishop of Orkney, appears in this attestation. The Earl had also a daughter, Elisabeth, married to Sir John de Drummond (see above). [She is also stated to have been married to Sir John Edmondston - see Shetland County Families] It is stated in several works that he was first married to Florentina, daughter of the King of Denmark, by whom be had no issue. The only Danish sovereign to whom this could apply would be Waldemar III, flourished 1340-75. It is further stated by one historian [Hay's Genealogie] that in 1363 there was a marriage concluded between the Earl of Orkney and a daughter of Magnus II, King of Sweden, being sister to Hakon VI of Norway, suzerain to the Earl.

In addition to the issue enumerated previously, this Earl had a daughter, Marjory wife of Sir David Menzies of Wemyss, to whom the administration of the Isles was entrusted during the minority of his nephew, William, the 44th Earl. Another son, William, obtained, on the 19th August 1407, a safe conduct to England for six weeks therefrom, and Thomas Sinclair, mandatory in Orkney, 1426, was evidently also a son of this earl. [From Nisbet's Heraldry]

NOTE - Commission of Bailliary by Lady Marjorie Menzies in 1418, to John, her son and heir, and nomination by Henry Earl of Orkney, wherein the Earl styles Sir David Menzies his brother-in-law.

It will be observed that Hay's account of the manner of the Earl's death agrees with the Diploma, both stating that he was slain in the Orkneys while resisting an invasion from the South, and elsewhere is found anno 1404: "A squadron, under Sir Robert Logan, attacked an English fleet of fishers off Aberdeen. Some good ships of Lynn happened to come up in time to aid their countrymen, and Logan himself, with the rest of his company, was taken. The English then landed on some of the Orkneys and spoiled them". [Holinshed]

NOTE from Peterkin's Rentals, 1503: "Hoy - Brabuster beneath the hill was an uris land, which the first Earl Henry gave to the vicar three penny land for the holding of a mass in Hoy one day each week for ever".

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