When Sir William died in July 1453, he was buried in the Lady Aisle, just south of the choir in St Giles' Kirk. A chapel was to be built on the south side of the Lady Aisle, in which a chaplain was to celebrate mass and offer prayers for his soul on each anniversary of his death. This was later called Preston Aisle. The relic of St Giles disappeared during the Reformation a century later, and there is no trace of the memorial plaques or arms today. The Preston arms can still be seen however, on the easternmost pillar of the south choir arcade, immediately next to the bay where the high altar stood.

Sir William Preston II b.xxxx d. c.1478 was succeeded by his son Sir Simon Preston III. One of the first duties of Sir Simon was to take custody of James III's younger brother, John, Earl of Mar. Resentful of his two brothers' popularity and warned by a witch, suitably prompted by the princes' political enemies, that he would die by the hand of his nearest of kin, the king had already imprisoned the elder of his brothers, Alexander, duke of Albany. Albany, however, had escaped from the Edinburgh Castle and fled to the French court. Bishop John Lesley's History next records that the king's second brother, the earl of Mar, 'wes takin in the nicht in his awin house, had to Cragmillar, and keipit thair at the Kingis commaund, and wes convict of ane conspiracie be witchecrafte agains the King'. The unfortunate man was then brought to a house in Canongate and while seated in a bath, 'they cuttit ane of his vanes and causit him bleid to dead'.

In August 1511, James IV erected the lands which Sir Simon Preston III was holding at Craigmillar, including the 'castle, fortalice and mill', into a free barony, for which the annual rent was to be a penny Scots at Whitsun.

Apparently, Sir William Preston II also had a son Sir Thomas Preston who was the castle chaplain from 1523.

Sir Simon Preston IV was to have a long and eventful career as laird of Craigmillar. His connections with the city of Edinburgh were also close. In 1538-43 and 1544-45 he served as provost, following a family precedent already established by his forebears Sir Henry Preston in 1434-39 and James Preston in 1525. (First mention of James Preston and he is not shown in the lineage chart.) In addition to Craigmillar, Sir Simon also possessed a town house opposite the town cross, on the site now occupied by the City Chambers (formerly the Royal Exchange.)

The first major event to affect Craigmillar under Sir Simon Preston IV was an English invasion of Scotland. In May 1544, following the Scots' repudiation of an agreement made earlier at Greenwich to form an alliance between Scotland and England by marrying the young Queen Mary to Prince Edward, the son and heir of King Henry VIII, the earl of Hertford landed with an army in Leith with a view to persuading the Scots to change their minds. An anonymous history of the period tells us that the army 'past to Craigmillar, quhilk was haistilie gevin to thame, promesand to keip the samyne without skaith [damage]: quhilk promes thai break, and brunt and destroyit the said hous'. A rather different interpretation of the apparent ease with which the English took the castle, however, is given by the Bishop John Lesley, who casts the city's provost in the unflattering role of a collaborator. Lesley relates that the merchants of Edinburgh had taken most of their valuables to Craigmillar for safe keeping: but that this, 'not without froaud of the keparis, as wes reported, wes betrayed to the Inglishmen for a parte of the bowtaine [booty] and spoill thairof'. If the accusation was true, it could have done Sir Simon little good, for he was himself taken prisoner and made to walk as far as London before being released.

In 1549, Sir Simon Preston IV was once more in Edinburgh, when he and his second wife Elizabeth Menteith, were granted a charter for the barony of Preston. A stone panel bearing the Preston coat-of-arms and the date 1549 which formerly surmounted the outer main gate of Craigmillar indicates that Sir Simon did not delay in making food the damage which the castle had suffered five years before. The construction of this period seems to have included the rebuilding of the east and south-east ranges around the inner court, and building (or rebuilding) of a strong outer wall around the castle, defended by rounded towers pierced by wide-mouthed gun-ports.

In the years following the return of Mary Queen of Scots from France, in August 1561, Sir Simon Preston IV was to show himself to be one of the queen's most loyal supporters. In 1562, he won Mary's gratitude when, as governor of Dunbar Castle, he failed to carry out a sentence of execution passed on the rebel earl of Huntly. In October of 1562, Mary nominated him once more for the position of provost of Edinburgh, but it was not until August 1565 that the burgh council would agree to accept him. He held the post until 1568, and between 1565 and 1567 also served as a privy councillor.

In September 1563, Mary spent a week at Craigmillar Castle as a guest of Sir Simon Preston IV. While there she received Thomas Randolph, the ambassador of Queen Elizabeth I, who warned her that if she wished to remain on friendly terms with England she should find herself an acceptable husband. Mary's eventual choice was the Catholic, Henry, earl of Darnley, whom she married on 29 July 1565. Darnley was not liked by Mary or her supporters and in December 1566, she spent some time at Craigmillar and a group of her advisors also meeting at Craigmillar made a fateful decision that would seal the fate of her unwanted husband. The pact was subsequently known as the Craigmillar Bond. Conspirators included the earls of Argyll, Huntly and Bothwell. Early in 1567 Darnley returned to Edinburgh from Glasgow. Mary suggested they spend some time at Craigmillar but he elected to stay at his own town house, Kirk o'Fields, just next to the town wall. On the nite of Feb. 9/10, 1567, the house was blown apart by an explosion. The next day when Darnleys body was found it was discovered he had been strangled.

Sir Simon Preston IV died sometime before 1575, but had already been succeeded as laird of Craigmillar by his son David in June 1569.

In Feb. 1593, Sir David Preston was succeeded by his son, Sir George Preston III.

May 18, 1625, George Preston III was succeeded by his brother Sir Robert Preston. Sir Robert died without issue in 1639. Craigmillar then passed to a distant relative.

In 1639, the estate passed to Sir David Preston b. c.1600 of Whitehill, descended from the first Sir Simon. Sir Simon Preston II had three sons, including a Sir Andrew Preston. Sir David Preston was the descendent of Sir Andrew Preston. Sir David Preston (II) married Susana Colville and had 3 children:

Thus ended the Prestons of Craigmillar, 1374 to 1660. There has to be a lot of other Prestons descended from these Prestons. Perhaps a John born 1726 (Walnut Grove Prestons) or another John born about 1699 (Smithfield Prestons) or perhaps a Philip born about 1715.....who knows.

The document goes on to talk about Craigmillar under the Gilmours. Much of the above is quoted directly from the document but I did not include everything. No estimate of dates of birth were given, all such estimates were made by me. My parents had a picture of the castle at Craigmillar for as long as I can remember. Not sure where it came from. They always thought they descended from these Prestons.