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Alice was born Alice Chaucer, daughter to Thomas Chaucer and Matilda Burghersh. Her grandfather was the poet Geoffrey Chaucer, writer of The Canterbury Tales. When she was 11 she married Sir John Philip. The couple lived briefly at Donnington Castle, but Sir John died within a year. Sir John, also entitled Lord Dennington, had married Maud, the widow of Walter Cookesey of Caldwall Castle, Kidderminster in the County of Worcestershire. Sir John lived at Caldwall Castle during his marriage to Maud and upon her death married Alice Chaucer. Sir John, a close personal friend of Henry V, died of dysentery after the successful siege of Harfleur in Normandy. Sir John is buried at St. Mary's Church in Kidderminster, Worcestershire. Later, after 1421, Alice married Thomas Montacute, 4th Earl of Salisbury (who died in 1428). Finally, in 1430, she married William de la Pole, Earl and later Duke of Suffolk, by whom she had a son John in 1442 (who became 2nd Duke of Suffolk in 1463). William became constable of Wallingford Castle in 1434. Alice was a lady-in-waiting to Margaret of Anjou in 1445. William was steward of the household to Henry VI, and fom 1447 to 1450 was the dominant force in the council and chief minister to the king; as such he was particularly associated with the unpopular royal policies whose failures culminated in the anti-court protest and political violence of Cade's Revolt in 1450.
In 1450 William was impeached by the Commons in parliament, but Henry VI intervened to exile his favourite rather than have him tried by the Lords. On his way across the Channel his vessel was intercepted by The Nicholas of the Tower whose crew subjected him to a mock trial, after which he was beheaded and the body thrown overboard. William's remains were recovered from a beach at Dover, and Alice had her husband buried at the Carthusian Priory in Hull, founded in 1377 by his grandfather, Michael de la Pole, first Earl of Suffolk. After William was killed, his properties including the castle and Honour of Wallingford and St Valery passed to Alice. She survived many challenges to her position, including a state trial. Whilst she had benefited from Lancastrian connections, she switched to supporting the House of York during the Wars of the Roses. In 1455 she was custodian of the Duke of Exeter at the castle. She was officially castellan at Wallingford until at least 1471 and possibly until her death in 1475. In 1472 Alice became custodian of Margaret of Anjou, her former friend and patron. A wealthy landowner, Alice de la Pole held land in 22 counties, and was a patron to poet John Lydgate. She is buried in an elaborate church monument incorporating a Cadaver tomb at St Mary's Parish Church, Ewelme, Oxfordshire.