James Douglas, 4th Earl of Morton (c. 1516 – 2 June 1581, aged 65) was the last of the four regents of Scotland during the minority of King James VI. He was in some ways the most successful of the four, since he won the civil war that had been dragging on with the supporters of the exiled Mary, Queen of Scots. However, he came to an unfortunate end, executed by means of the Maiden, a predecessor of the guillotine. Biography Early life James Douglas was the second son of Sir George Douglas of Pittendreich, Master of Angus, and Elizabeth Douglas, daughter of David Douglas of Pittendreich. He wrote that he was over 61 years old in March 1578, so was probably born around 1516. Before 1543 he married Elizabeth, daughter of James Douglas, 3rd Earl of Morton, and became known as the "Master of Morton". In 1553 James Douglas succeeded to the title and estates of his father-in-law, including Dalkeith House in Midlothian and Aberdour Castle in Fife. Elizabeth Douglas suffered from mental illness, as did her two elder sisters, who were married to Regent Arran and Lord Maxwell. James and Elizabeth's children did not survive to adulthood, except three daughters who were declared legally incompetent in 1581. James also had five illegitimate children. At the start of war of the Rough Wooing, James and his brother David communicated with Henry VIII of England on the possibility of their surrendering Tantallon Castle to the English army that burnt Edinburgh in 1544. The English commander Lord Hertford wrote to the Master of Morton in April 1544, discussing his journey towards Berwick-upon-Tweed, and hoping he could leave the castles of Dalkeith and Tantallon in the hands of allies. However, four years later he defended Dalkeith Palace against the English and was captured in June 1548, "sore hurt on the thigh", and taken as a hostage to England. After the Treaty of Boulogne in 1550, James was exchanged for the English soldier John Luttrell, returned from captivity in England, and began to use his title of "Earl of Morton". James's political activities and allegiances during the Scottish Reformation were at first equivocal in 1559, but in February 1560 he signed the Treaty of Berwick which invited an English army into Scotland to expel the Catholic regime of Mary of Guise. He took part in the unsuccessful embassy to England in November 1560