castle for around five days in 1334. Helmsley Castle remained in the possession of the de Roos family until 1478 when Edmund de Roos sold it to Richard, Duke of Gloucester who later became Richard III. Richard did nothing to the castle, staying instead at Middleham Castle. After Richard III's death at the Battle of Bosworth, Helmsley Castle was restored to Edmund de Roos by Henry VII. Edmund died childless in 1508 and the castle passed to his cousin Sir George Manners of Etal on whose death in 1513 his son Thomas inherited it. He was created Earl of Rutland in 1525. On his death in 1543, Thomas was succeeded by his son, Henry, but it was under the rule of his grandson Edward, that the castle was altered next. He had the old hall converted into a Tudor mansion, converted the 13th-century chapel into a kitchen linked to the old hall by a covered gallery, and knocked the new hall down. The south barbican was converted into a more comfortable residence at this time. A letter of April 1578 describes the slow progress of the mason's work (and the payment of a £10 sum to the mason), and that timber was available for a gallery in the attic of the mansion. On Edward's death in 1587 his brother John Manners inherited the castle, followed by John's son Roger, and then Roger's younger brother Francis. On the death of Francis in 1632 the castle passed to George Villiers, 1st Duke of Buckingham through his marriage to Katherine, Francis's daughter. During the English Civil War, the castle was besieged by Sir Thomas Fairfax in 1644. Sir Jordan Crosland held it for the king for three months before surrendering. Parliament ordered the castle to be slighted and much of the walls, gates and part of the east tower were destroyed. However the mansion was spared. The castle had by this time been inherited by George Villiers, 2nd Duke of Buckingham who married Mary, daughter of Thomas Fairfax in 1657. After his death in 1687 the castle was sold to Charles Duncombe in 1695. He was a banker and politician who was knighted in 1699 and became Lord Mayor of London in 1708. The 40,000 acre estate was purchased for the sum of £90,000 (roughly £11,000,000 in 2018). His sister Mary's husband, Thomas Brown, inherited the castle on Charles's death in 1711. Thomas