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The Myddelton family had been prominent in the affairs of North Wales since at least the fifteenth century. Robert Myddelton, the son of Rhirid ap David of Penllyn (alive 1393-1396), assumed the surname of his mother, Cecilia daughter and heir of Sir Alexander Middleton of Middleton in the parish of Chirbury, Shropshire. Robert's grandson David Myddelton was receiver-general for North Wales, during the reigns of Edward IV and Richard III. David's son Ffoulke Myddelton was governor of Denbigh castle, as was Ffoulke's son Richard Myddelton (c.1508-1575).
Richard's son Sir Thomas Myddelton (1550-1631) was a founder member of the East India Company, and a benefactor of the lucrative expeditions by Drake, Raleigh and Hawkins. His wealth enabled him to buy the castle and lordship of Chirk for £5,000 from St John of Bletsloe in 1595. Sir Thomas had been apprenticed to a London grocer, and became a freeman of Grocers' Company in 1582, surveyor of the outports c.1580 and by 1595 was employed on public business such as the valuing prize cargoes, raising emergency military and naval supplies, and giving advice on currency problems. Sir Thomas was MP for Merionethshire 1597 and lord lieutenant 1599, lord mayor of London 1613, and MP for the city of London 1624-1626. In 1615 he acquired an Essex manor as a country seat nearer to his place of business in Tower Street, and also bought other properties in the Home counties. In 1628-1629 he purchased the crown lordship of Arwystli and Cyfeiliog, which he later resold.
The heir to Sir Thomas's Welsh estates was his oldest surviving son, Thomas Myddelton (1586-1666), who purchased Ruthin Castle in 1632, and acquired the stewardship and lordship of Ruthin in 1635. He entered parliament in 1624 as MP for Weymouth, before changing to Denbighshire in 1625. He was also elected for the Long parliament. He became a Parliamentary commander during the Civil War. After the restoration of the monarchy, Chirk Castle underwent a programme of major building work, during which the family lived at Cefn-y-wern until 1672.
Sir William Myddelton (1694-1718), 4th baronet, died unmarried, when the baronetcy became extinct, and the Chirk Castle estate, with the lordships of Chirk, Chirklands and Ruthin passed to Robert (dsp. 1733), younger son of the 1st baronet. Robert was succeeded by his brother, John (d. 1747). During the 18th century the Myddelton family developed coal mines at Black Park and an iron forge at Pont-y-blew. On the death of John's grandson, Richard Myddelton (d. 1796), the estate was divided between his sisters. The Chirk Castle estate passed to his eldest sister, Charlotte, wife of Robert Biddulph of Ledbury, Herefordshire, who prefixed his surname with Myddelton. The Ruthin Castle estate passed to Harriet, who bequeathed the estate to her sister, Maria (d. 1843), wife of Frederick West (d. 1852), third son of John, Earl De La Warr.
According to the 1873 return of owners of land, Richard Myddelton-Biddulph of Chirk Castle owned an estimated 6,953 acres (all in Denbighshire and Merionethshire), with an estimated rental of £9,128.