It was passed to his illegitimate son, George Douglas, later created Earl of Angus, and despite several sieges, it remained the property of his descendants for much of its history.
It was sold by the Marquis of Douglas in 1699 to Hew Dalrymple, Lord North Berwick and the ruin is today in the care of Historic Environment Scotland.
Tantallon is a unique construction within Scotland, the defences comprising only a single large wall securing a coastal promontory.
The south-east, north-east, and north-west approaches are naturally defended by steep sea cliffs and were only ever protected by relatively small defensive walls.
The curtain wall is built of the local red sandstone and has a tower at each end and a heavily fortified gatehouse in the centre, all of which provided residential accommodation.
[3] A north range of buildings, containing a hall, completed the main part of the castle, enclosing a courtyard around 70 by 44 metres (230 by 144 ft).
[1] There are also similarities between Tantallon and "courtyard" castles, such as Doune, which also dates from the late 14th century, and is entered via a passage beneath a strong keep tower.
[4] Seven storeys high, this tower would have formed the lord's "donjon", or keep, containing his private accommodation, and connecting to the hall in the north range.
[7] The main entrance ran through a passage below, protected by a drawbridge, three pairs of doors, a portcullis, and machicolations; holes in the ceiling enabling the defenders to drop missiles on to intruders below.
Only a small section of the other walls remains to the east, and contains a postern gate, giving access to the sea through a cleft in the cliffs below.
Within the outer ditch are two mounds, which Charles McKean suggests may conceal 16th-century caponiers, defensive positions allowing covering fire along the trench.
[8] A stone-fronted mound formerly ran along the outside of the ditch, although only a 30-metre (98 ft) section of the outer wall survives, at the south end, terminating in a two-storey round tower.
[5] This tower, with several gun ports, was built prior to the siege of 1528, and may have been inspired by the new artillery defences at nearby Dunbar Castle.
[6] A map of the area, dated to before 1300, shows a castellated site with the name of "Dentaloune",[10] possibly a corruption of the Brythonic din talgwn or "high-fronted fortress".
[4] In 1377, the Earl of Angus made his close friend, Alan de Lawedre of The Bass, Constable of Tantallon Castle, an office he held until at least 1389.
[15] Several attempts were made to dislodge the Countess, but an agreement was formalised by Parliament in April 1389, and George Douglas was recognised as Earl of Angus, being the heir of his mother.
On 11 October 1491, Tantallon Castle was besieged by James IV, with guns sent from Edinburgh and Linlithgow, and crossbows and culverins (a primitive type of handgun) from Leith.
[21] She left valuable costume and jewels behind at Tantallon, including several borders for hoods called "chaffrons" and a diamond that had been a present from Louis XII of France.
[23] In 1525, Angus, with support from Henry VIII of England, staged a virtual coup d'état, taking custody of the young King, and becoming Chancellor.
But, in 1528, the sixteen-year-old James V escaped, and, joining his mother at Stirling, pronounced Angus attainted, banishing him to "north of the Spey".
[26] Alexander Jardine of Applegarth, the Master of Artillery, consulted with Robert Borthwick and John Drummond about the cannon and equipment required.
[27] The castle was bombarded with this cannon for 20 days, although the King's guns could not be brought close enough to the walls to do substantive damage, due to the deep outer ditch.
[25] Angus wrote to the Earl of Northumberland, that James V had brought Scottish and French engineers, "ingenious men", to the siege without success, "as can be rememberit, thar was nevir sa mekill (so much) pane travell expensis and diligence done and maid for the wynning of ane house, and the sammyn (same) escaip in Scotland, sen it was first inhabit.
Pitscottie described this operation: "the king caused masons come and ranforce the wallis, quhilkis war left waste before as transis (passages), and through-passages; and maid all massie work, to mak it the more strang.
"[34] On Angus' return in 1542, he was still in contact with Henry VIII, and allowed Sir Ralph Sadler, English ambassador to Scotland, to reside at Tantallon during the attempts to negotiate a marriage between the infant Mary, Queen of Scots, and Edward, Prince of Wales in 1542–43.
[4] In 1650, during the Third English Civil War, Oliver Cromwell's Parliamentarian forces invaded Scotland, taking control of the south of the country after their victory at Dunbar in September.
The ruins of Tantallon were sold, in 1699, to Sir Hew Dalrymple, the President of the Court of Session, who also owned the Barony of North Berwick, the Bass, Fidra and other properties in the area.
There, they were used in the training of RAF bomber crews (including 617 Squadron, the famous "Dambusters") who were part of a massive effort to deceive the Germans as to the actual location of the Allied invasion.
Beginning on the night before the D-day landings, thin strips of aluminium foil were to be dropped by the bombers near two locations far from Normandy.
Actors Scarlett Johansson and Michael Moreland are depicted on the roof, then cautiously descending the narrow inside staircase.