Lochlainns, some of whom claimed to be kings of all Ireland, Derry also sank into unimportance.
The famous skeleton on the city's coat-of-arms is said to depict the association with another aristocratic family, the Norman de Burgos, who built their great fortress at Greencastle at the entrance to Lough Foyle. They briefly owned part of Derry in the early fourteenth century and may well have been planning to build a new town there. Instead, the settlement declined in significance. When the local O'Doherty family built a castle in Derry for their overlords the O'Donnells, probably around 1500, it may well have been thought that a new beginning was about to be made. The recently-built O'Doherty Tower is a modern attempt to commemorate that medieval association.
Throughout the second half of the sixteenth century, Queen Elizabeth I's military leaders tried to conquer the province of Ulster, the only part of Ireland still outside English control. The English first came to Derry in 1566 but the garrison established there at that time lasted only a few years. A second, more successful garrison returned in 1600 during the 'Nine Years War' against the Gaelic O'Neill and O'Donnell earls. On this occasion the English managed to hold on to Derry and, when the war came to an end in 1603, a small trading settlement was established and given the legal status of city. In 1608 this 'infant city' was attacked by Sir Cahir O'Doherty (a previous supporter of the English in Ulster), and the settlement was virtually wiped out.
This attack came about shortly after the so-called 'flight of the earls' when the O'Neill and O'Donnell chieftains, together with their principal supporters, fled to the continent, leaving Gaelic Ulster leaderless. The new king in London, James I, decided on a revolutionary plan designed once and for all to subordinate Ulster. The 'Plantations in Ulster' required the colonising of the area by loyal English and Scottish migrants who were to be predominantly Protestant in religion, unlike the Catholic Irish. One part of this colonisation was to be organized by the ancient and wealthy trades' guilds of London. The new county granted to the Londoners and its fortified city, built on the site of the recently destroyed settlement, were renamed Londonderry in honour of this association . The city of Londonderry was the jewel in the crown of the Ulster plantations. It was laid out according to the best contemporary principles of townplanning, imported from the continent (the original street lay-out has survived to the present almost intact). More importantly, the city was enclosed by massive stone and earthen fortifications Derry was the last walled city built in Ireland and the only city on the island whose ancient walls survive complete. Among the city's new buildings was St. Columb's Cathedral (1633). This is one of the most important seventeenth century buildings in the country and was the first specifically Protestant cathedral erected in these islands following the Reformation.
The new city was slow to prosper. By the 1680's it still had only about 2,000 inhabitants; and yet it was, by far, the largest town in Ulster. Along with most parts of Britain and Ireland, the city suffered from the upheavals in the 1640's. In 1649 the city and its garrison, which supported the 'republican' Parliament in London, were besieged by Presbyterian forces loyal to the King. Among its most famous citizens in the second half of the seventeenth century was George Farquhar, one of the so-called Restoration dramatists.
On April 18 1689, James came to Derry and summoned the city to surrender. The King was rebuffed and actually fired at by some of the more determined defenders. As a policy ot no surrender' was confirmed, the Jacobite forces outside the city began the famous Siege of Derry. For 105 days the city suffered appalling conditions as cannonballs and mortar-bombs rained down, and famine and disease took their terrible toll. Conditions for the besiegers were no better and many thousands of people died, both inside and outside the walls. 