Henry Sinclair, 1st Earl of Orkney
also referred to as:
"Prince" Henry Sinclair, Earl of Orkney

Robert Sewell    This page was set up by Robert Sewell in April 2002 to show the descent of Henry Sinclair, Earl of Orkney, who is reputed to have sailed to North America 100 years before the voyages of Christopher Columbus.  Robert Sewell graduated from McMaster University (Hamilton, Ontario, Canada) in 1967 with a B.Sc. degree in chemistry.  After a year of studies at the University of Toronto's College of Education, he taught high school science in Collingwood, Ontario for a year and then taught chemistry, physics and general science in Hamilton, Ontario for twenty-nine years.  Robert Sewell retired from teaching in June 1998.  He may be contacted by email from September to May at the following address:

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Henry Sinclair
The Legendary Voyages
Ancestors of Henry Sinclair
Descendants of Henry Sinclair

Henry Sinclair, 1st Earl of Orkney
Arms of Sinclair
    Henry Sinclair is reputed to have been born about 1345, and was proclaimed Lord of Rosslyn upon the death of his father in 1358.  Henry married first to a granddaughter of the King of Norway and Sweden, but she died shortly thereafter before they had any children.  On the death of his maternal grandfather, Malise, Earl of Stratherne, Orkney, and Caithness he became one of the competitors for the earldom of Orkney, the others being his cousins, Aleander del Ard and Malise Sperra, Lord of Skaldale. These three proceeded to Norway, where, having submitted thier claims to King Hakon VI, he, at Marstrand on August 2, 1379 formally invested Henry as Earl of Orkney and Lord of Shetland, under certain restrictions. The Earl was to govern the islands and to enjoy the revenues during the King's pleasure, but was not to build any castles, and was to be answerable to the King's Court at Bergen.  At his death the earldom was to revert to the Crown of Norway if he left no sons, and if he did they were to be re-invested. In defiance of the terms of his charter he built the Castle of Kirkwall.  Henry had a charter from King Robert III of the castlewards of Pentland and Roslin, built the dungeons of Roslin and certain walls thereabout, and laid out parks for fallow and red deer.

    In 1389 Henry attended the coronation of King Eric of Norway.  In 1391 he was engaged in the conquest of the Færoe Isles, and at this point legend becomes mixed with history. Henry is said to have met the Venetian voyager Nicolò Zeno, who happened to be wrecked there, and was appointed  by Henry to be captain of his fleet.  Having conquered the Færoes, he next descended on Shetland, where Malise Sperra had established himself, and with the assistance of Zeno, Sperra was defeated and slain with seven of his followers near Tingwall.  With the brothers Antonio and Nicolò Zeno, Henry is next reputed to have set out to discover a rich and populous country in the far west which had been stated to exist by fishermen, who alleged they had been driven there by a storm.  Encountering fog they drifted south to the west of Ireland and landed at Icara (Kerry), from whence they sailed north-west and, according to legend, came to Greenland.

    It is entirely possible that Henry Sinclair visited Greenland about 1392 at which time there may have been some Norse colonies there, although they would most definitely have been in a state of decline.  The last Bishop of Greenland known to have visited his see died in 1372.  Henricus (Erik) was consecrated as Bishop of Greenland in 1389, but there is no record of him ever finding a ship to take him there.  A ship from Norway spent a winter at an abandoned Greenland settlement circa 1406 - 1410 and found only wild cattle and no people.  Unfortunately, there is no actual historical record or evidence of Henry Sinclair having visited Greenland, and we can only say that he is reputed to have done so and that such a voyage would have been quite possible.

    As Earl of Orkney, Henry was entitled to impose taxes and wear a crown if he chose to do so.  Because of this, he is referred to as "Prince Henry Sinclair, Earl of Orkney", although it appears that he was never actually granted the title of Prince.  Regardless, he was a vassal of the Kings of both Scotland and Norway, and was a man of considerable wealth and power with his own fleet of 13 ships that plied between Norway, the Orkneys and Rosslyn.  He was also the Duke of Oldenburg in Denmark, Admiral of the High Seas for Scotland and Lord Chief Justice of Scotland.

    Henry Sinclair was slain circa 1400 - 1404.  An English expedition was sent to conquer the Orkneys in August 1400, and he may have been slain by the English invaders around that time.  Scot's Peerage states:  ". . . he was slain in 1404, while resisting an invasion from the south." (Vol. VI, page 569)

The Legendary Voyages

    Henry Sinclair is alleged to have left the Orkneys in early April 1397 or 1398 with 12 or 13 ships and journeyed to what is now Newfoundland and Nova Scotia. Most of the ships then returned to the Orkneys; but two remained in the New World, journeyed on to Massachusetts and Rhode Island, and returned the next year.  Some details of this legend are as follows:

The Zeno Brothers:  The Venetian brothers Nicolò and Antonio Zeno were ship wrecked on the Island of Frislanda (thought to be The Færoes) where the local prince named Zichmni (thought to be Henry Sinclair) is said to have hired one or both of them as navigators or admirals.  The Zeno brothers sent a record of this voyage including the famous "Zeno Map" back to a third brother Carlo "the Lion" Zeno in Venice.  Regardless of their exact role, the Zeno Brothers are a part of the legend.  The Zeno Map and manuscript relating the details of the voyage were kept secret until 1558 when a descendant, also named Nicolò, decided to make a printed book of it.
    It has also been suggested that Zichmni was a Baltic pirate named Wichmann and that the Zeno brothers were involved in pirating when they were supposed to have been exploring and map making.

For more on the Zeno Brothers and their map, please see:
The Zeno Map at:  http://www.pibburns.com/mewhinne/5a-1.htm

Newfoundland:  They landed, but were attacked and driven off by native people.  They managed to replenish their food, water and wood supplies at a nearby site, but were once again driven off and a number of men were killed.
    Visitors recently returned from Newfoundland report that the hospitality displayed by the inhabitants of that province in the early 21st century has improved dramatically since the late 14th century.

Nova Scotia:  They landed in Nova Scotia in late May or early June and found the native Micmac Indians friendly. Henry Sinclair became known as "Glooscap", the white Micmac god.  He built a castle and buried the Holy Grail (and perhaps the Arc of the Covenant as well) in a mysterious deep shaft on Oak Island.  All except two ships returned to the Orkneys, and Henry Sinclair wintered in Nova Scotia during which time he and his men built a larger ship . . . or so the story goes.

Arms of the Clan GunnMassachusetts and the Westford Knight:  Next spring, Henry Sinclair and his men sailed south and landed in Massachusetts.  At that point, Sir James Gunn died and a memorial was inscribed on a rock on Prospect Hill in Westford, Massachusetts.  This memorial is described by some as nothing more than a crudely pecked outline of an 18th century tomahawk while other describe it as a Knight Templar in armour carrying a sword and a shield bearing the arms of the Clan Gunn.

    For more about the Westford Knight, please see:

The Westford Knight: Tracing of the Rock Effigy at:  http://sinclair.quarterman.org/sinclair/effigy.html

Rhode Island and the Newport Tower:  Later the same year, Henry Sinclair is reputed to have sailed on to Rhode Island where he built the mysterious Newport Tower, which is also said to have been built by the Vikings in the 11th century and by Portuguese explorers in 1511.
    The best evidence, supported by radioisotope dating, suggests that the Newport Tower was built as a windmill during the 17th century.

    For more about the Newport Tower, please see:

Newport's Mystery Tower at: http://www.unexplainedearth.com/newport.php

For more on the legendary nature of Henry Sinclair's voyage, please see:
Earl Henry Sinclair's ficticious trip to America
Earl Henry Sinclair: The Legendary Atlantic Crossing

Ancestors of Henry Sinclair

The following record is based on Sir James Balfour Paul's The Scot's Peerage, Vol. VI, pp. 564 - 571; except where stated otherwise.

I. Robert de Saint Clair, in Normandy, married Eleanor de Dreux, relict (widow) of Hugh, Lord Chateauneuf and daughter of Robert, second Count de Dreux, in France, by Joland de Coucy, his wife. Sir Robert had issue:
  • Sir William, shown next.
II. Sir William Sinclair was Sheriff of Edinburgh 1266, 1288-90; of Haddington 1264-90; Linlithgow 1264-90; Dumfries 1288; and Justiciar of Galwythie 1288-89. He was guardian to Alexander, Prince of Scotland, 1279-81 who predeceased his father in 1283-84.  Was granted a Charter by King Alexander III, on April 8, 1280, of the baxter (border) lands of Innerleith, and a charter of the lands and barony of Roslin, on September 14, 1280. He was one of the garrison who defended the Castle of Dunbar in 1296 against Edward I, and on its surrender , on March 25, 1296, was sent a prisoner in the Tower of London.
    Sir William Sinclair is said to have married Agnes, who may have been a daughter of Patrick, Earl of Dunbar. Agnes may or may not be the same person as Amicia, described as a "widow of William St. Clair, dwelling in the county of Edinburgh" who had a two years protection from Edward I. on April 7, 1299. Sir William had issue:
  • Sir Henry, shown next.
  • William, who succeeded Matthew do Crambeth as Bishop of Dunkeld in 1312.
  • Annabel, who married first to Sir Robert Bisset, and secondly to Sir David Wemyss.
  • Gregory (perhaps) who is said to the be the ancestor of the Longformascus family.

    Note:  Thanks to W. Darcy McKeough who has shared a report by James Dinwoodie, Scots Ancestry Researcher, which states: "In 1162, in the reign of King Malcolm IV, the Norman knight Sir Henry de Sainte Claire settled in Lothian.  It was not until 1280, in the reign of Alexander III that Henry's great great grandson Sir William de St. Clair was granted the lands of Rosslynn or Roslin in Lothian five miles south of Edinburgh."

III. Sir Henry St. Clair of Roslin swore fealty to Edward I on 13 June 13, 1292. However, he was one of the garrison of Dunbar Castle, where he was taken prisoner in 1296 and sent to England. He was exchanged in 1299; and about September 15, 1305 was appointed Sheriff of Lanark by Edward I. Sir Henry appears to have switched sided frequently; he eventually supported the Bruce, and fought against the English at Bannockburn.
    On October 21, 1314, Sir Henry had a Charter from King Robert, of all His Majesty’s lands on the Muir of Pentland, and a further Charter from Edward de Gourton of the part of the lands of Gourton, tenanted by Roger de Hauewood, dated the Friday after the feast of St. Bartholomew, August 28,  1317. He was one of the Barons of Scotland, who signed the letter dated April 4, 1320 to Pope John XXII, asserting the independence of Scotland. 
    Sir Henry married Alice de Fenton who survived him. He died before January 28, 1335/36; and left issue:
  • Sir William, shown next.
  • John, who accompanied his brother Sir William on the expedition to the Holy Land with the heart of Bruce. He was murdered, as was his brother, by the Saracens in Andalusia, Spain, on August 25, 1330.
IV. Sir William St. Clair had a grant of a pension of £40 in anticipation of his services in the Holy Land 1329, being one of the knights chosen to accompany Sir James Douglas to Palestine with the heart of Bruce, but was murdered, as was his brother, by the Saracens in Andalusia, Spain on August 25, 1330. He left issue:
  • William, shown next.
  • Margaret, who married first to Thomas Stewart, Earl of Angus who died in 1361 and secondly to Sir John Sinclair of Hermandston.
  • Thomas (perhaps) who was Bailie of Orkney for the King of Norway and left a son:
    • Alexander
  • John (perhaps) who was a witness in 1367.
    Note:  According to Florence Van Rensselaer: The Livingston Family in America and Its Scottish Origins: New York, 1949, page 26; Sir William St. Clair was "a Baron of Normandy" who "married a daughter of Richard, Duke of Normandy."
V. William Sinclair of Roslin was a minor when his father died, and succeeded to the pensions of his father and his Uncle John.  He had a Charter from King David II of the lands of Morton and Merchamyston in Midlothian, on the resignation of William Bisset on February 10, 1357/58. He had a safe conduct to go to England on May 6, 1358 on his way abroad to Prussia to fight in foreign wars.  On September 17, 1358 King David II confirmed to him  an annuity granted to his grandfather Sir Henry S. Clair. 
    William married Isabella, second daughter of Malise, 8th Earl of Strathearn, Earl of Orkney and Caithness and his wife Marjorie, a daughter of Hugh, 4th Earl of Ross and Lady Maud Bruce, a sister of Scotland's national hero, King Robert the Bruce. Marjorie was a sister of William, 5th Earl of Ross. William Sinclair left issue:
  • Henry, shown next.
  • David, who had a charter under the Great Seal of the lands of Newburgh and Auchdale in Aberdeenshire in exchange for any rights which he had in Orkney and Shetland, derived from his mother, dated April 23, 1391.
VI. Henry Sinclair, 1st Earl of Orkney, the main subject of this page. He was born circa 1345 and died (slain) circa 1400 - 1404. He married circa 1370-74 to Jean Haliburton, daughter of  either Sir Walter Halyburton of Dirleton or Sir John de Halyburton of Dirleton and his wife Margaret Cameron. (please see below)
    Henry was invested Earl of Orkney and Lord Zetland, by King Haakon of Norway, at Marstrand, Norway on August 2, 1369. According to legend, he visited Greenland and North America in 1390's.
Sinclair Arms from Scots Peerage

Henry Sinclair and his descendants

Generation One
Henry Sinclair, 1st Earl of Orkney
Born circa 1345
Acceded on the death of his father in 1358 when he was only 13 years old
Died (slain) circa 1400 - 1404
According to legend, Henry Sinclair visited Greenland circa 1391/92.  He is also reputed to have voyaged to what is now Newfoundland, Nova Scotia, Massachusetts and Rhode Island circa 1398.

According to Sir John Balfour Paul:  The Scots Peerage, 1904 - 1914, Vol. VI, p. 569, Henry Sinclair married to Jean Halyburton, a daughter of Sir Walter Halyburton of Dirleton.

According to Florence Van Rensselaer: The Livingston Family in America, New York, 1949, pg. 28, Henry Sinclair married circa 1370 -1374 to Jean de Haliburton, a daughter of Sir John de Haliburton of Dirleton and Margaret Cameron. Sir John was a son of Sir Walter Halyburton. Ms. Van Rensselaer gives as her reference Sir James Balfour Paul:  The Scots Peerage, 1904 - 1914, Vol. IV, pp. 330 - 338; corrections in Vol. IX, p. 102.

Regardless of Jean's exact parentage, she and Henry had the following children:

     At this point, we have a conundrum. Was Beatrix a daughter of the 1st or 2nd Earl of Orkney? Beatrix is shown in The Scots Peerage as a daughter of Henry Sinclair, 2nd Earl of Orkney and his wife Egidia Douglas. When Beatrix married James "the Gross", 7th Earl of Douglas, she would have been marrying her mother's uncle. Beatrix would have been both a daughter-in-law and great granddaughter of Archibald "the Grim", 3rd Earl of Douglas. 

Please click HERE to learn why this could not be so.

     To further complicate this issue, it would seem that Burke's Peerage, (Genealogical Books Ltd, 2003), volume 1, page 438 shows another Beatrix or Beatrice Sinclair who married Sir William Borthwick. I have not seen this edition of Burke's, but web pages citing this and other references include:
  • thePeerage.com where Beatrice's father is shown as the 1st Earl of Orkney and her mother is not shown thereby introducing the possiblilty that this Beatrice may have been a "natural" or illegitimate daughter of Henry Sinclair, 1st Earl of Orkney. 
  • Leo's Genealogics Website where neither her mother nor father are shown.
worried cat
I have shown Beatrix as a daughter of the 1st Earl of Orkney.
However, I am open to suggestions.
Please send any information to Robert Sewell

Generation Two
Lady Beatrix Sinclair
Born circa 1400 - 1404, perhaps after the death of her father.
Died before February 8, 1462
Married before March 7, 1425 to James "the Gross", 7th Earl of Douglas, a son of Archibald "the Grim", 3rd Earl of Douglas.  Sir James Douglas was of Balvany in Banffshire, and was created Earl of
Avondale and Lord Balvany before becoming the 7th Earl of Douglas.
Beatrix and James had the following children:
Genertion Three
Lady Janet Douglas
Married before 1451 to Robert, 1st Lord Fleming, a son of Sir Malcolm Fleming and Elizabeth Stewart who was a granddaughter of King Robert II of Scotland.
Janet and Robert had the following daughter:
For Beatrice Fleming's descent from the Kings of Scotland
through her father, Robert, 1st Lord Fleming,
click on The Kings of Scotland Page.

Generation Four
Beatrice Fleming
Beatrice married to James Livington 3rd Lord Livingston of Callendar and they had a son:

For the continuation of this line, click on Livingston of Callendar

Sources used for this page include the various internet links given throughout the page as well as:
Sewell Vincent Sample: Letters, 2002.
Samuel Eliot Morison: The European Discovery of America, New York, 1971.
Florence Van Rensselaer: The Livingston Family in America, New York, 1949.
Sir James Balfour Paul:  The Scots Peerage, 1904 - 1914, Vol. VI, pp. 564 - 571.
Brian Tompsett:  Royal Genealogy at:  http://www.hull.ac.uk/php/cssbct/genealogy/royal/

For another story of pre-Columbian discovery of North America, 
click on Prince Madoc.

Please visit the Sewell Genealogy Site Map for other pages in this series.


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