The Douglases transferred the King to the house of the Archbishop of St Andrews in the Cowgate of Edinburgh, where George Douglas could keep a more secure watch with 40 men.
[8] When Lennox and Angus joined in battle 2 miles west of Linlithgow on 4 September 1526, George Douglas was sent to bring a force raised in Edinburgh and the young King.
[citation needed] A letter written by George Douglas is the earliest source of the story that James V made Oliver Sinclair of Pitcairn commander of his army before the battle of Solway Moss.
[9] After the death of James V, George Douglas and his brother the Earl returned to Scotland in January 1543, in the company of a number of Lords taken prisoner at Solway Moss.
[10] Viscount Lisle, the Lord Warden of the Border, heard that George was welcomed in Scotland, and stayed with Arran till midnight on 15 January 1543 at Holyroodhouse.
[13] The family historian David Hume of Godscroft records an anecdote that George Douglas is used to build consensus for the English marriage.
Regent Arran was still minded to come an agreement with Henry VIII, and a council of the nobility had decided to send him and Lord Maxwell to London as ambassadors with their conclusions.
[16] Douglas offered the Sadler the insight that the Earl of Lennox and the clergy would form a faction or party against Regent Arran, and this would inevitably force him further into Henry's pocket to "work him at his will".
[19] On 1 July George was back in London as a commissioner completing the Treaty of Greenwich which was intended to bring peace between England and Scotland and secure the royal marriage plan.
George told Sadler after the meeting that the Cardinal was compliant and wished only to obtain Henry's and Arran's favour but feared the Scottish abbeys would be suppressed.
[21] Despite George's efforts, Regent Arran and the Scottish Parliament rejected the Treaty of Greenwich in December 1543, resulting in the war of the Rough Wooing.
Edward Seymour, Lord Hertford landed an army at Leith on 3 May 1544 which burnt Edinburgh,and Arran released the brothers, who made a bond with him to support the French marriage plan.
In June George sent the Scottish Rothesay Herald to Guise to take her letters to London and advised her to tell Francis I of France to deal only with her, not with Arran.
[25] In February 1545, George sent a letter to Henry VIII, to be forwarded by his English contact Ralph Eure, (who was killed at the battle of Ancrum Moor).
George wrote that the war was losing Henry's support in Scotland and offered advice;"the Scots are informed that you would make gentlemen no better than shepherds, and by reason of the extreme war that uses killing women and young children and Scots prisoners that come forth of England, gentlemen say that Your Majesty will have a plane conquest of this realm, and that you will kill men women and children.
"[26]A month before the battle of Pinkie, on 9 August 1547 the Earl of Hertford, now Duke of Somerset, Lord Protector of England, told the Scottish ambassador Adam Otterburn that if George Douglas would negotiate at Newcastle-upon-Tyne he might not invade Scotland.
Otterburn advised Arran to allow Douglas to negotiate, writing that he would work for the commonwealth of both realms and to avoid the shedding of Christian blood.
[29] In 1548, George Douglas maintained communication with an English commander, William Grey of Wilton who made him captain of Yester Castle and Dalkeith.
George's former allies, the East Lothian lairds John Cockburn of Ormiston and Alexander Crichton of Brunstane had assisted Grey, who also commended "Newton the Scot" who fought for him at Dalkeith.
[31] In September 1549, the English soldier Thomas Holcroft hoped to organise the capture of George Douglas and facilitate the release of the St Andrew's castle Castilians who were prisoners in France.