George Douglas of Rumgally and Helenhill was a Scottish courtier and diplomat. He was involved in the escape of Mary, Queen of Scots from Lochleven Castle in May 1568. After the battle of Langside he accompanied her to England. He was involved in plans to return Mary to rule in Scotland and carried letters written in cipher code.

Little Geordie Douglas George Douglas was a son of Robert Douglas of Lochleven and Margaret Erskine. He was a younger brother of William Douglas of Lochleven, later Earl of Morton.Historie and Life of King James the Sext (Edinburgh, 1804), p. 36. He is said to have been called "P[r]ettie Geordie",Lord Herries, Historical memoirs of the reign of Mary queen of Scots and a portion of the reign of king James the Sixth (Edinburgh, 1837), p. 101. and the English diplomat Thomas Randolph called him "pettie George Douglas".William K. Boyd, Calendar State Papers Scotland, 8 (Edinburgh, 1914), no. 326. Robert Bowes called him "little George Douglas".Bowes Correspondence, p. 538. The French historian Louis Wiesener noted that Mary and James VI called him the "petit singe", the little monkey, in their correspondence.Louis Wiesener, "Cinque lettres inédites de Marie Stuart", Revue des questions historiques, 3 (Paris, 1867), p. 492

Willie Douglas, who also took a leading role in Mary's escape from Lochleven, was sometimes called "Little Douglas" or "litle William Dowglas".Papers Relating to the Master of Gray (Edinburgh, 1835), p. 36. Willie was said to be an orphan, or George's half-brother or nephew. He was a servant at Lochleven Castle.Agnes Strickland, Lives of the Queens of Scotland: Mary Stuart, 6 (Edinburgh: Blackwood, 1856), p. 64: Agnes Strickland, Letters of Mary, Queen of Scots, 1, p. 71.

George Douglas acquired the lands of Rumgally near Cupar by marriage, and in May 1582 bought Helenhill in Fife near St Andrews, now known as Allanhill. Rumgally is sometimes spelled "Rumgawy" in older publications.Geographical collections relating to Scotland made by Walter Macfarlane, 2 (Scottish History Society, 1900), p. 158.

Mary, Queen of Scots, and Lochleven Castle Mary, Queen of Scots, was taken to Lochleven Castle after the battle of Carberry Hill in June 1567. For a time, she was she able to make grants using the privy seal, and she rewarded John Drysdale and George Douglas, who was given an income from the lands of Tillicoultry. Drysdale was a servant of the laird of Lochleven, William Douglas. He bought supplies for Mary at Lochleven.Gordon Donaldson, Register of the Privy Seal, 5:2, p. 400: Exchequer Rolls of Scotland, 20 (Edinburgh, 1899), p. 47. Another servant at Lochleven, James Drysdale, became an enemy of Willie Douglas and threatened Mary.Alexandre Labanoff, Lettres de Marie Stuart, 2 (London: Dolman, 1844), p. 264.

George Buchanan wrote that Mary and George became familiar while playing a game during moments of leisure.James Aikman, History of Scotland by George Buchanan, 2 (Glasgow, 1827), p. 531.W. A. Gatherer, The Tyrannous Reign of Mary Stewart: George Buchanan's Account (Edinburgh, 1958), p. 73. George Douglas is said to have become a firm ally of Mary, Queen of Scots, when she was compelled to abdicate at Lochleven in July 1567.Gordon Donaldson, All the Queen's Men: Power and Politics in Mary Stewart's Scotland (London: Batsford, 1983), pp. 64, 69. Claude Nau wrote that Douglas spoke to Mary and undertook to prevent her enemies taking her from the castle to a worse fate.Joseph Stevenson, The History of Mary Stewart by Claude Nau (Edinburgh, 1883), pp. 62, 266. Mary would later claim Douglas as a witness to her forced abdication. A memoir of Mary's captivity sent to Cosimo I de' Medici by his ambassador in Paris, Giovanni Maria Petrucci, names George Douglas and Robert Melville as witnesses to her being threatened and pressured to abdicate.Alexandre Teulet, Lettres de Marie Stuart: Supplement (Paris, 1859), p. 279: Alexandre Labanoff, Lettres de Marie Stuart, 7 (London: Dolman, 1844), p. 319.

By October 1568, William Drury heard of suspicions that there was "over great familiarity" between Mary and George Douglas.Allan James Crosby, Calendar State Papers Foreign Elizabeth, 1566–8 (London, 1871), p. 363 no. 1792. In April 1568, Drury heard a rumour that when James Stewart, 1st Earl of Moray visited the castle, Mary had talked about marrying again "and named one to her liking, George Douglas, brother to the laird of Lochleven". At this time, Lord Methven was also mentioned as a possible husband for the captive queen. The Spanish ambassador in London, Diego Guzmán de Silva pointed out that such a marriage for Mary to a mutual relation would benefit Moray's rule as Regent. Mary made her first attempt to escape the island on 25 March, dressed as her laundress.Thomas Wright, Queen Elizabeth and Her Times, 1 (London: Colburn, 1838), p. 266Thomas Finlayson Henderson, Mary Queen of Scots and her Environment, 2 (London: Hutchinson, 1905), p. 485: Martin Hume, Calendar State Papers Spain (Simancas), 2 (London: HMSO, 1894), pp. 22 no. 15, 25–26 no. 17.

Moray (who was George's half-brother) had George excluded from the island.Joseph Stevenson, The History of Mary Stewart, from the murder of Riccio until her flight into England (Edinburgh, 1883), p. 77, 159. George Douglas stayed nearby at Kinross waiting for Mary to make her getaway. His parents had built a new mansion, known as the "New House", at the site of the Kinross House.Margaret H. B. Sanderson, Mary Stewart's People (Edinburgh: James Thin, 1987), p. 69. John Drysdale secretly carried letters between Mary and George.Antonia Fraser, Mary Queen of Scots (Phoenix Press, 2002), p. 435: Thomas Wright, Queen Elizabeth and Her Times, 1 (London: Colburn, 1838), pp. 266–267, 269.James Aikman, History of Scotland by George Buchanan, 2 (Glasgow, 1827), pp. 531–532.

Accounts of Mary's escape from the castle on 2 May 1568 vary, possibly conflating reports of an earlier attempt. George Douglas is said to have exchanged signals and tokens with the Queen's chamberer Marie Courcelles,Registrum Honoris de Morton, 1 (Edinburgh, 1853), p. 29. including a pear-shaped pearl earring,Joseph Stevenson, The History of Mary Stewart by Claude Nau (Edinburgh, 1883), pp. 88, 288: Thomas Finlayson Henderson, Mary Queen of Scots and her environment, 2 (London: Hutchinson, 1905), p. 487. and rowed the boat from the island, or waited on the shore with John Beaton and horses for her ride to Niddry Castle and the west of Scotland.Jade Scott, Captive Queen: The Decrypted History of Mary, Queen of Scots (London: Michael O'Mara Books, 2024), p. 72: John Parker Lawson, History of the Affairs of Church and State in Scotland by Robert Keith, 2 (Edinburgh, 1845), p. 796.Retha Warnicke, Mary Queen of Scots (Routledge, 2006), p. 165: Thomas Finlayson Henderson, Mary Queen of Scots and her Environment, 2 (London: Hutchinson, 1905), p. 484. Claude Nau mentions that Willie Douglas was in charge of boats on the loch, and he is also said to have taken the castle keys while the Laird was at supper.Antonia Fraser, Mary, Queen of Scots (World Books, 1970), p. 394: Joseph Stevenson, The History of Mary Stewart, from the murder of Riccio until her flight into England (Edinburgh, 1883), pp. 78, 280. A report sent to England gave this account:George Douglas, brother to the Laird of Loughleven, who was in fantasy of love wythe hir, and had provyded this money of before, met her at the loughe side, accompanyd with the laird of Ricarton [Alexander Hepburn], a friend of the Lord Bothwelles, and with them in company ten horse. They took away all the horses which pertained to the Laird of Lochleven so that he should not be able to followe.Joseph Stevenson, The History of Mary Stewart, from the murder of Riccio until her flight into England (Edinburgh, 1883), p. ccii: Joseph Bain, Calendar State Papers Scotland, 2 (Edinburgh: HMSO, 1900), p. 404 no. 652, from TNA SP 52/15 f.25.

Claude Nau, Mary's secretary, wrote that George's mother Margaret Erskine gave counsel against the escape.Joseph Stevenson, The History of Mary Stewart by Claude Nau (Edinburgh, 1883), pp. 86–89, 287, 289. David Hume of Godscroft noted that some previous writers thought Margaret Erskine, had no foreknowledge of the escape, while others thought "she had a hand in it" and suggested that Margaret Erskine took pity on the Queen because she had promised to pardon her allies and give preferment to her younger son George Douglas.David Reid, History of the House of Angus by David Hume of Godscroft, vol. 1 (Edinburgh: STS, 2005), pp. 172–173.

England and France After the battle of Langside, Mary went to England. George Douglas and Willie Douglas joined her at Carlisle Castle.Joseph Bain, Calendar State Papers Scotland, 2 (Edinburgh: HMSO, 1900), p. 422 no. 685. Later, Willie was sent away and Mary thought he had been attacked, perhaps by James Drysdale (possibly a brother of John Drysdale who had helped her escape from Lochleven). Mary heard reports that James Drysdale resented Willie Douglas's "good service" and had vowed to kill him.Alexandre Labanoff, Lettres de Marie Stuart, 3 (London: Dolman, 1844), pp. 263–264.

Mary understood that George Douglas was to be removed from her household at Carlisle and decided to send him to France as her messenger.William Turnbull, Letters of Mary Stuart (London: Dolman, 1845), pp. 162–163:Joseph Stevenson, The History of Mary Stewart, from the murder of Riccio until her flight into England (Edinburgh, 1883), p. 189. On 26 June 1568, Mary sent Douglas to Elizabeth I and to France with her letters.Alexandre Teulet, Lettres de Marie Stuart: Supplement (Paris, 1859), p. 272. Mary wrote to the French ambassador in London, Jacques Bochetel de la Forest, asking him to obtain a passport for Douglas and give him money.Jade Scott, Captive Queen: The Decrypted History of Mary, Queen of Scots (London: Michael O'Mara Books, 2024), pp. 38, 264 fn. 4."Carlisle Castle Mary Queen of Scots letter sells for £32.5k", BBC News, 3 February 2022British Library Add MS 89480, 26 June 1568 Douglas also carried letters from Mary for Elizabeth, and for Charles IX of France and Catherine de' Medici. The texts of these letters refer to Douglas as their bearer or "porteur".Joseph Bain, Calendar State Papers Scotland, 2 (Edinburgh: HMSO, 1900), p. 705 no. 4: Alexandre Labanoff, Lettres de Marie Stuart, 2, pp. 122–128.

Mary asked Elizabeth to grant Douglas a passport to France, where he would reside for a time and learn French.Agnes Strickland, Letters of Mary Scots, 1 (London: Colburn, 1842), p. 57. He was to give Elizabeth copies of letters written by Moray's secretary John Wood. Mary hoped that the letters would undermine Elizabeth's support for Moray.Agnes Strickland, Lives of the Queen of Scotland and English Princesses, 6 (New York: Harper, 1857), p. 153.

George Douglas arrived in London with a companion who was thought to be Mary's secretary.Martin Hume, Calendar State Papers Spain (Simancas), 1568–1579, 2 (London, 1894), p. 50 no. 36. Mary had written to Charles IX that Douglas was her faithful servant "having rescued me from the clutches of my mortal enemies at the risk of his life and estrangement from his closest family". He was entrusted to recount Mary's narrative to Charles IX and Catherine expanding on the contents of her letters.Agnes Strickland, Lives of the Queen of Scotland and English Princesses, 6 (New York: Harper, 1857), pp. 155–156: Alexandre Labanoff, Lettres de Marie Stuart, 2, p. 126. She had also composed a memoir of events which stated that George Douglas and Robert Melville would be able to bear witness that she been compelled by force to sign the abdication papers at Lochleven.Alexandre Teulet, Papiers d'État Relatifs à l'Histoire de l'Écosse, 2 (Paris: Plon, Bannatyne Club, 1851), p. 246.