Baron Henry SINCLAIR

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• FamilySearch ID: LVX2-L85
• _UID: 70AF9723A5EF4934B6FF7C01EDE550E11F73

Henry married Margaret HEPBURN in 1488. Margaret (daughter of Adam HEPBURN and Helen HOME) was born about 1467 in Hailes, Prestonkirk, East Lothian, Scotland; died in 1542. [Group Sheet] [Family Chart]

1. Helen (Elinor) SINCLAIR was born about 1493 in Newburgh, Foveran, Aberdeenshire, England; died on 2 Jan 1562 in Airlie, Forfarshire, Scotland.

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• FamilySearch ID: GQPK-RZ6
• _UID: D957498F9A304AFAB862A213A705354F15DD

William married Christina LESLIE on 29 Apr 1458. Christina (daughter of George LESLIE and Christian HALYBURTON) was born about 1439 in Rothes, Fifeshire, Scotland; died before 16 Mar 1500. [Group Sheet] [Family Chart]

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• _UID: 48E92B4A8B47452F916091090E06EB970D9F

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• Clan: ; Clan Sinclair
• FamilySearch ID: LCCN-H49
• Name: William SINCLAIR
• _UID: A16D21FEEAE945E29CD2A7FC7AB46F21F63D
• MilitaryService: 1436, Scotland; Sinclair was high admiral of Scotland
• TitleOfNobility: Between 1454 and 1456, Scotland; Chancellor of Scotland
• TitleOfNobility: 16 Sep 1476, Fife, Scotland; Feudal Baron of Ravenscraig and Dysart

William married Elizabeth DOUGLAS about 1431 in Scotland. Elizabeth (daughter of Archibald DOUGLAS, 4th Earl of Douglas and Lady Margaret STEWART) was born in 1401 in Douglas, Lanarkshire, Scotland; died in 1451 in Traquair, Scottish Borders, Scotland, United Kingdom; was buried in 1451 in Traquair, Scottish Borders, Scotland, United Kingdom. [Group Sheet] [Family Chart]

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• FamilySearch ID: LCCP-BCX
• TitleOfNobility: ; Countess of Buchan
• TitleOfNobility: ; Countess of Ross
• _UID: A3A34B6730434281A1F34EAFE93E488AB8B4

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• _UID: 88407C2867634C1A83ED3130D039C8498774

George married Christian HALYBURTON. Christian and died. [Group Sheet] [Family Chart]

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• _UID: F468D68F3A4C4793AB607DAEBFCCA9AE39E8

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• FamilySearch ID: MF13-35Q
• MilitaryService: ; captured following the Battle of Homildon Hill in 1402,
• TitleOfNobility: ; 10th Baron Of Roslin
• TitleOfNobility: ; 2nd Earl of Orkney
• Occupation: ; Chief Justice of Scotland
• Occupation: ; Pantler of Scotland
• _UID: 4D35D17117344B008864C1356354C788427D

Notes:

The Life Summary of Henry
When Sir Henry Sinclair II, Baron Of Roslin, 2nd Earl Of Orkney was born in 1389, in Orkney Islands, Orkney, Scotland, United Kingdom, his father, Henry 1st Earl of Orkney Baron of Rosslyn Sinclair, was 37 and his mother, Jean Haliburton, was 39. He married Countess Egidia Jill Douglas of Orkney on 17 February 1404, in Perthshire, Scotland, United Kingdom. They were the parents of at least 4 sons and 6 daughters. He died on 1 February 1422, in Roslin, Midlothian, Scotland, at the age of 33, and was buried in Midlothian, Scotland.


Henry Sinclair, 2nd Earl of Orkney (c. 1375 ? 1420) was a Norwegian nobleman and Planter of Scotland.

He was son of Henry Sinclair, the Earl of Orkney, by his wife Jean, daughter of John Halyburton of Dirleton. Sinclair was one of those captured following the Battle of Homildon Hill in 1402, but released on ransom. He had succeeded his father, de facto, as Earl by 1404; there is no record that he was ever officially installed as Earl, and no certain record that he ever visited his Earldom.

He was one of those who accompanied James Duke of Rothesay on his journey to France aboard the Maryenknyght, which was captured by English pirates off Flamborough Head in 1406. He followed the prince into captivity, but was soon released. Subsequently he was often in England on business connected with the king's imprisonment. He also spent some time in the service of the Duke of Burgundy.
In about 1407 he married Egidia Douglas, daughter of Sir William Douglas of Nithsdale and maternal granddaughter of King Robert II of Scotland.

*William Sinclair, last Jarl of Orkney, and first Earl of Caithness
*Beatrix Sinclair, who married James Douglas, 7th Earl of Douglas.
Henry Sinclair died of influenza c. 1420.

===
additional information:
The son: William Sinclair, 1st Earl of Caithness, 3rd Earl of Orkney and founder of Rosslyn Chapel married three times - Elizabeth Douglass Dowager Countess of Buchan (who was also a wife of a Douglas previously) Marjory Sutherland of Dunbeath (the wife which shows up in the genealogy here) and Janet Yeman.

Henry married Egidia (Jill) DOUGLAS on 17 Nov 1407 in Perth, Perthshire, Scotland. Egidia (daughter of Sir William DOUGLAS and Princess Egidia STUART, Of Scottland) was born about 1375 in Nithsdale, Dumfriesshire, Scotland; died about 1438 in Orkney Islands, Orkney, Scotland; was buried about 1438 in Orkney Islands, Orkney, Scotland. [Group Sheet] [Family Chart]

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• FamilySearch ID: LRPD-JTK
• TitleOfNobility: ; Countess of Orkney
• Name: Jill DOUGLAS
• _UID: 01DD4444D66C462B9B44534276C7276253E7

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• FamilySearch ID: GJY2-KSJ
• TitleOfNobility: ; Earl of Wigtown, Annandale, Galloway, & Bothwell
• TitleOfNobility: ; Prince of Scotland
• TitleOfNobility: ; Sir Knight
• Name: Archibald "Tyneman" DOUGLAS
• Name: Archibald DOUGLAS
• Occupation: ; Marechal of France
• MilitaryService: 14 Sep 1402, Homildon Hill, Wooler, Northumberland, England; Fought at Battle of Homildon Hill and was captured by the English, but escaped

Notes:

Archibald was the Duke of Touraine, Earl of Wigtown, Lord of Annandale, Lord of Galloway, Lord of Bothwell and the 13th Lord of Douglas. He was thus a Scottish nobleman and warlord. At times Archibald was given the nickname of Tyneman, which in the old Scottish language means loser. This may have been in reference to his great uncle Sir Archibald Douglas as well.

The Early Years
Archibald was the illegitimate son of Archibald Douglas and Joanna de Moravia of

threave-castle

Threave Castle


Bothwell. He was either born at Threave Castle or Bothwell Castle. Until Archibald's accession he was known as Master of Douglas. In 1390, when he was twenty years old he married Princess Margaret of Carrick. Margaret was the daughter of King Robert III of Scotland. It was at about this time that his father had bestowed upon him regalities of Ettrick Forest, Lauderdale and Romannobridge and Peeblesshire. Then on June 4, 1400 at the age of thirty, the King of Scotland, Robert, had appointed Archibald the keeper of Edinburgh Castle for the remainder of his life, with a pension of two hundred marks a year.

bothwell-castle

Bothwell Castle


Renewal of Percy vs. Douglas
In 1400, at Candlemas, the Earl of March, George I, and Henry 'Hotspur' Percy had entered Scotland lying waste as far as Papple in East Lothian. The villages of Traprain, Markle and Hailes were burned to the ground and two unsuccessful attempts were made at Hailes Castle. Now the Master of Douglas, who had also held the office of Lord Warden of the Marches, surprised them by night at their camp near East Linton and would then defeat the English Force. Archibald had managed to chase his enemy as far as Berwick upon Tweed, slaughtering any stragglers in the woods close to Cockburnspath.

The Siege of Edinburgh
Later on that year, in summer, Archibald would be made second in command to David Stewart, the Duke of Rothesay who was Lieutenant of the Kingdom, during the siege of Edinburgh Castle by Henry IV. Henry would be unsuccessful in his endeavors. With Owain Glyndwr's rebellion gathering in Wales he would become the last English monarch that would ever invade Scotland in person.

Archibald's father died later on that year at Christmas. Before his passing, he held vast lordships that stretched from Galloway, Douglasdale, Moray, and Clydesdale to the shires of Stirling and Selkirk. He also was lord over the forfeited lands of the Earl of Dunbar in Lothian and the Merse.

Two years later, Archibald's brother-in-law and heir to the throne, David Stewart, the Duke of Rothesay, was held captive. He was first held at Bishop's Palace at St. Andrews, then at the Royal Palace of Falkland. While here, Duke David would pass away on the 27th of March. It has been alleged that he had died under mysterious circumstances. He was only twenty-four and had been in good health prior to his passing. Rumors were started saying that he David had been starved to death in the Falkland's pit prison. Prince David was also arrested under a warrant that had been issued in the name of his father, by his uncle, Robert Stewart, the Duke of Albany, and Douglas. Both Albany and Douglas were rumored to have been the authors of any foul play that was suspected. This can be shown by the fact that both of the men were summoned to appear before Parliament.

On the 16th of March both of the men were acquitted when Parliament had passed an act that stated that the Prince had "departed this life through Divine Providence, and not otherwise". This would clear both of the men from High Treason and any other crime. Any of the king's subjects were strictly forbid to make the slightest imputation on their fame. This action could be considered to be a whitewash, as the Kingdom of Scotland couldn't afford to lose its two most powerful men due to the renewed English hostility. Archibald and Albany were considered to be the only fit antidote to the traitor Earl of March and his English allies.

Homildon Hill
On the 22nd of June 1402, a small Scottish force would be beaten by George Dunbar, the Earl of March's son, at the Battle of Nesbit Moor. Archibald would lead a raid with Murdoch of Fife, Albany's son, as far as Newcastle to avenge this battle. At the head of 10,000 men, Archibald, and his men would lay waste to all of Northumberland.

George Dunbar would persuade Henry Percy, the 1st Earl of Northumberland, and his son Harry "Hotspur" Percy to lie in wait for the returning Scots at Wooler. Once Archibald's men had made their camp at Millfield, which was relatively low ground, the English would rush them. The Scots, however, had keen sentries and the army was able to retreat to the higher ground of Homildon Hill.

bendorstonehomildon

Homildon Hill memorial marker today


At Homildon Hill they organized themselves in the traditional Schiltron formations. Archibald didn't learn any lessons from his great uncle's Battle at Halidon Hill seventy years before. The Schiltrons had presented a large target for the English long bowmen, and the formations began to break. A hundred men, under Sir John Swinton of the Swintons of that Ilk, had decided to charge the enemy saying "Better to die in the mellay than be shot down like deer". All would die.

schiltron-formation-ex-braveheart

Schiltron Formation represented in the movie Braveheart


It has been suggested that Archibald had hesitated to signal the advance of his main force, but when he did, it was too little too late. Archibald's mauled army would meet with the, as yet unbloodied, English men at arms and were routed. Many of his leading captains would be captured, including his kinsman George Douglas, the 1st Earl of Angus, Thomas Dunbar, the 5th Earl of Moray, and Murdoch of Fife. Archibald himself would be captured as well, after he was wounded five times, including the lose of his eye.

If the Percys and other English knights had thought that they had gained great immediate riches from their ransoms, they were to be disappointed. They would receive a message from King Henry congratulating them for their victory but forbidding the release of any of their prisoners.

In 1403, Henry Hotspur was in an open rebellion against the king and joined his kinsman, Thomas Percy, the Earl of Worcester, while Owain Glyndwry was undertaking a campaign against the English rule in Wales. Hotspur would set free his Scottish captives and Archibald, with his co-prisoners, decided to fight alongside their former captors. In the chivalric spirit of the time, Archibald marched with his former enemy, Hotspur, and his forces to meet with King Henry IV at the Battle of Shrewsbury. The result of this battle of a decisive Royalist victory. Henry Hotspur would be killed by an arrow through his mouth. Archibald was, yet again, captured. This time he would suffer from a loss of a testicle, after he had fought gallantly on the field and personally had killed Edmund Stafford, the 5th Earl of Stafford and Sir Walter Blount.

Prisoner of King Henry
Archibald was now a captive of King Henry IV. The cost for the ransom of the Scot nobles that were taken at Homildon would prove to be difficult for the impoverished Scottish exchequer. When Prince James of Scotland was also captured while en route to France by some English pirates in 1406, the position would seem to be impossible.

The aged King Robert III would die of his grief not long after. The Kingdom of the Scots was now in the hands of the Duke of Albany de jure, as well as de facto.

king-henry-iv-of-england

King Henry IV


After giving an oath on the Holy Scripture to King Henry to be his man above all others, except for King James, and on the production of suitable hostages for his parole, Archibald was allowed to return to his estates to carry out his private affairs. He would agree, again under oath, to return to captivity in England on an appointed day.

At Easter, Archibald went north and hadn't returned on his aforesaid day. King Henry wrote to his regent, Albany, complaining of this "un-knightly" behavior and had warned him that, unless Archibald would return the other hostages would be dealt with at his pleasure. Archibald still did not return. After a payment of 700 merks in 1413 to the King of England, Henry V, the hostages were released.

Political Machinations
In 1412, Archibald would go to Flanders and then to France. After he had arrived in Paris he would start negotiations with John 'The Fearless', Duke of Burgundy. They would end up agreeing to a mutual defense and offense pact in their respective countries.

Archibald had also resumed his duties as the Lord Warden of the Marches not long after returning to Scotland. While at the border he had free reign to defend it and to keep the peace. However, it appears that Albany wasn't prepared to do this. Archibald would recover his costs from his customs fees on all trade goods that were entering the country.

Then in 1416, while King James was still a hostage in England, Archibald had visited London twice to enter negotiations for his release. While he was there the Lollard faction, during Henry V's absence in France, had tried to persuade the Scottish delegates to go on an offensive. Albany decided this to be the opportune moment to reclaim Berwick-upon-Tweed. He gathered an army to take it and then despatched Archibald to Roxburgh Castle, which was also held by the English.

When the Scots had learned of the huge army that was led by King Henry's brother, John of Lancaster, the 1st Duke of Bedford, and Thomas Beaufort, the Duke of Exeter, they decided to retreat. Following their devastation in Teviotdale and Liddesdale, and the burning of the towns of Selkirk, Jedburgh and Hawick, the raid was known as the "Foul Raid".

The Great Scottish Army
Archibald's son, the Earl of Wigtoun, were fighting in France along with his son-in-law, Buchan, They were able to inflict a heavy defeat over the English at the Battle of Bauge in 1421.

Archibald married Lady Margaret STEWART in 1390 in Scotland. Margaret (daughter of King Robert III STEWART, of Scotland and Annabella DRUMMOND, Queen of Scotland) was born in 1370 in Dunfermline, Fifeshire, Schotland; died in Sep 1456 in Thrieve Castle, Galloway, Scotland; was buried in Sep 1456 in Dumfries, Dumfriesshire, Scotland. [Group Sheet] [Family Chart]

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Marriage and issue
In 1390 he married Lady Margaret (d.1451), eldest daughter of John Stewart, Earl of Carrick, who later became King Robert III. Of their children:

Archibald Douglas, 5th Earl of Douglas, and Wigton, &c., (1390? 1439), who succeeded to the earldom.
Elizabeth (d. c. 1451), who married first John Stewart, 2nd Earl of Buchan, secondly Thomas, son of Alexander Stewart, Earl of Mar, and thirdly William Sinclair, 3rd Earl of Orkney (d. 1480).
William Douglas (b. before 1401)
Sir James Douglas (d. 17 August 1424)
Mary Douglas, who married Sir Simon Glendinning of Parton. Their daughter Janet married Gilbert Grierson 1st Lord of Lag.
Douglas in Literature