Archibald Douglas , 4th Earl of Douglas Archibald Douglas , Duke of Touraine , Earl of Douglas , and Wigtown , Lord of Annandale , Galloway 13th Lord of Douglas , ( 1372 – 1424 ) was a Scottish nobleman and warlord . He is sometimes given the epithet " Tyneman " ( Old Scots : Loser ) , but this may be a reference to his great - uncle Sir Archibald Douglas . Master of Douglas . The eldest legitimate son of Archibald Douglas , 3rd Earl of Douglas and Joanna de Moravia of Bothwell , he was born either at Threave Castle or at Bothwell Castle c . 1372 and was known as the " Master of Douglas " until his accession . By 1390 he had married the Princess Margaret of Carrick , a daughter of King Robert III of Scotland . Around this time , his father bestowed upon him the regalities of the Ettrick Forest , Lauderdale and Romannobridge , Peeblesshire . On 4 June 1400 , King Robert appointed him Keeper of Edinburgh Castle for life , on a pension of 200 merk s a year . Rites of Passage . Renewal of the Percy / Douglas feud . At Candlemas 1400 George I , Earl of March and Henry ' Hotspur ' Percy had entered Scotland and laid waste as far as Papple in East Lothian . The villages of Traprain , Markle and Hailes were burnt and two unsuccessful attempts were made to invest Hailes Castle . The Master of Douglas , who held the office of Lord Warden of the Marches , surprised them by night at their camp near East Linton and defeated the English Force . The Douglases chased the enemy away as far as Berwick upon Tweed , slaughtering many stragglers in the woods near Cockburnspath . Siege of Edinburgh . Later that summer Douglas was second in command to David Stewart , Duke of Rothesay , the lieutenant of the Kingdom , during the siege of Edinburgh Castle by Henry IV . Henry was unsuccessful in his endeavours and with Owain Glyndŵr ' s rebellion gathering apace in Wales , he became the last English monarch to ever invade Scotland in person . Inheritance . Archibald , the 3rd Earl died at Christmas 1400 , and the new 4th Earl became the largest and most powerful magnate in the realm . His father ' s vast lordships stretched from Galloway Douglasdale , Moray , Clydesdale to the shires of Stirling and Selkirk . These were augmented by the forfeited lands of the Earl of Dunbar in Lothian and the Merse . Death of Rothesay . In 1402 Douglas ' brother - in - law , the heir to the throne , David Stewart , Duke of Rothesay was held in close arrest , first at the Bishop ' s Palace at St Andrews , then at the Royal Palace of Falkland . At Falkland , Duke David died on 27 March , in what have been alleged to be mysterious circumstances . The Duke was 24 years old and in good health prior to his arrest , and rumours abounded that he had been starved to death in Falkland ' s pit prison . Prince David had been arrested under a warrant issued in the name of his father the decrepit Robert III , by his uncle , Robert Stewart , Duke of Albany and Douglas . Both Albany and Douglas , were rumoured to have been the authors of any foul play suspected . This can be shewn by the fact that both men were summoned to appear before Parliament . However on 16 March , both men were acquitted when Parliament passed an act stating that the Prince had : " " departed this life through Divine Providence , and not otherwise " " , clearing both of High Treason , and any other crime , and strictly forbidding any of the King ' s subjects to make the slightest imputation on their fame . This can be considered a whitewash , as the Kingdom of Scots could not afford to lose its two most powerful men due to renewed English hostility . Douglas and Albany were considered to be the only fit antidote to the traitorous Earl of March and his English allies . Homildon Hill . On 22 June the same year , a small Scots force was beaten by George Dunbar , the Earl of March ' s son , at the Battle of Nesbit Moor . Douglas led a punitive raid with Murdoch of Fife , Albany ' s son , as far as Newcastle to avenge the battle . At the head of 10 , 000 men he laid waste to the whole of Northumberland . March persuaded Henry Percy , 1st Earl of Northumberland , and his son Harry " Hotspur " Percy to lie in wait for the returning Scots at Wooler . Once Douglas ' men had made camp at Millfield , relatively low ground , the English army rushed to attack . The Scots did however have keen sentries and the army was able to retreat to the higher ground of Homildon hill , and organised into traditional Schiltron formations . Douglas had not learnt the lessons that had defeated his great uncle at the Battle of Halidon Hill seventy years previously . The Schiltrons presented a large target for the English Longbowmen , and the formations started to break . A hundred men , under Sir John Swinton of the Swintons of that Ilk , chose to charge the enemy saying : " Better to die in the mellay than be shot down like deer " . All perished . It has been suggested that Douglas hesitated to signal the advance of his main force , and when he did , it was too little too late . Douglas ' mauled army met the as yet unbloodied English men at arms , and were routed . Many of Douglas ' leading captains were captured , including his kinsman George Douglas , 1st Earl of Angus , Thomas Dunbar , 5th Earl of Moray and Murdoch of Fife . Douglas himself was captured having been wounded five times , including the loss of an eye . This wounding was despite the fact that it is alleged Douglas ' armour had taken three years in its construction . Captivity . With the Lords of the North . If the Percies and the other English knights thought they had gained great immediate riches from ransoms , they were to be disappointed . They received a message from King Henry congratulating them their victory but forbidding the release of any of their prisoners . By 1403 , Hotspur was in open rebellion against his King , joining with his kinsman Thomas Percy , Earl of Worcester and Owain Glyndŵr , Prince of Wales . Hotspur set free his Scots captives and Douglas with his co - prisoners decided to fight alongside their former captors . In the chivalric spirit of the time , Douglas marched with his former enemy Hotspur , and his forces to the meet with King Henry IV at the Battle of Shrewsbury . Fighting on the English king ' s side was George de Dunbar , 10th Earl of March , then in exile from Scotland . The result of the battle was another rout , Hotspur being killed by an arrow through the mouth . Douglas was once again captured , and suffered the loss of a testicle after having fought gallantly on the field and personally killing Edmund Stafford , 5th Earl of Stafford and Sir Walter Blount . Douglas had again tasted heavy defeat . Prisoner of King Henry . Douglas was now a captive of King Henry . The cost of ransom of the Scots nobles taken at Homildon was proving hard for the impoverished Scots exchequer . When Prince James of Scotland was captured " en route " to France by English pirates in 1406 , the position seemed impossible . The aged King Robert III died of grief it is said soon after . The Kingdom of Scots was now in the hands of the Duke of Albany " de jure " as well as " de facto " . Return to Scotland . After giving his oath on Holy Scripture to King Henry to be his man above all others excepting King James , and on the production of suitable hostages for his Parole , Douglas was allowed to return to his estates to carry out his private affairs . Douglas had agreed again under oath to return to captivity in England upon an appointed day . At Easter Douglas went north and did not return upon the aforesaid day . King Henry wrote to Regent Albany complaining of this " un - knightly " behaviour and warned that unless Douglas returned the hostages would be dealt with at his pleasure . Douglas did not return . Only upon payment of 700 Merk s in 1413 to the new King of England , Henry V were the hostages liberated . Lord of Annandale . In a political " volte - face " , the Earl of March had been accepted back into the political fold in Scotland . Both Douglas and Albany being reconciled to him . In 1409 March ' s lands in Lothian and the Merse were returned to him . This on condition of the Regent that his Lordship of Annandale be transferred to the Earl of Douglas . With his Lordship of Galloway , Douglas now controlled the whole of South west Scotland . The friendship between Albany and Douglas was confirmed in 1410 when they arranged the marriage of John Stewart , Earl of Buchan , Albany ' s oldest son with Elizabeth , daughter of Douglas . Political Machinations . Embassy to the continent . Douglas went to Flanders and France in 1412 , on arriving in Paris he entered into negotiations with John the Fearless , Duke of Burgundy whereby they agreed a mutual defence and offence pact in their respective countries . Warden of the Marches . Douglas had resumed his duties as Lord Warden of the Marches soon after his return to Scotland . On the Border he had a free rein to defend it and to keep the peace . However , it appears that Albany was not prepared to pay for this , so Douglas recovered his costs from customs fees on all trade goods entering the country . The Foul Raid . In 1416 , with King James still a hostage in England , Douglas twice visited London to enter negotiations for his release . Whilst there the Lollard faction , during Henry V ' s absence in France , tried to persuade the Scots delegation to go on the offensive . Albany decided that this would be an opportunity to reclaim Berwick upon Tweed and raised an army to take it . He despatched Douglas to Roxburgh Castle which was also held by the English . When the Scots learnt of a huge army led by King Henry ' s brother , John of Lancaster , 1st Duke of Bedford and Thomas Beaufort , Duke of Exeter , they retreated ignominiously . The following devastation in Teviotdale and Liddesdale , and the burning of the towns of Selkirk , Jedburgh and Hawick earned this title of the " Foul Raid " . The Great Army of Scotland . Douglas ' s son the Earl of Wigtoun had been fighting in France with his son - in - law Buchan , where they were able to inflict a heavy defeat over the English at the Battle of Baugé in 1421 . In 1423 Wigtoun and Buchan , arrived back in Scotland to raise more troops for the War effort , and personal request to the Earl of Douglas from Charles VII of France to lend his aid . Douglas ' ally and King Charles ' implacable enemy , John the Fearless of Burgundy had died in 1419 , so Douglas willingly consented to the French King . After considerable gifts to the church , Douglas left his son , the Earl of Wigtoun in Scotland . Wigtoun was charged with care of his estates and the negotiations for the release of King James , Douglas prepared for war . Douglas and Buchan sailed into La Rochelle with an estimated 6500 men on 7 March 1424 . Duke of Touraine and Lieutenant General of France . On 24 April Charles VII reviewed his new troops at Bourges . Douglas was given the post of " Lieutenant - General in the waging of war through all the Kingdom of France " . On 29 April , Douglas was granted the Duchy of Touraine , including the " Castle , town and city " of Tours , and the " Castle and town " of Loches . Douglas was the first foreigner and also the first non - royal to be granted Ducal status in France . Battle of Verneuil . The newly created French duke was defeated and slain at Verneuil on 17 August 1424 , along with his second son , James , and son - in - law John Stewart , 2nd Earl of Buchan . Douglas was buried in the choir of Tours Cathedral , alongside Sir James Douglas , his son . 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 : Douglas in Literature . The 4th Earl of Douglas is represented in William Shakespeare ' s " Henry IV , Part 1 " from the defeat at Homildon to his release following the Battle of Shrewsbury .