Sir Richard Cholmondeley (or Cholmeley) (c. 1460–1521) was an English farmer and soldier, who served as Lieutenant of the Tower of London from 1513 to 1520 during the reign of Henry VIII. He is remembered because of his tomb at the Tower of London and because he is fictionalized as a character in Gilbert and Sullivan's darkly comic opera, The Yeomen of the Guard. Cholmeley's name is frequently misspelled as Cholmondeley because of its misspelling in the plaque on his tomb, which led to the misspelling of the character's name in the opera; other branches of Cholmeley's family use the longer spelling.
Knighted in 1497 for valour in battle against the Scots, Cholmeley continued to serve as a soldier until 1513, becoming entrusted with many positions of responsibility for security of castles and fortifications in England. He was successful as a farmer and a shrewd investor in land, much increasing his family wealth. As Lieutenant of the Tower of London, he drew criticism for his reaction to the Evil May Day riots of 1517, when he ordered the firing of some of the Tower's artillery at the city to suppress rioting. He was also responsible for the rebuilding of the chapel of St Peter ad Vincula at the Tower. His illegitimate son, Roger Cholmeley, became Lord Chief Justice of the court of King's Bench.
Cholmeley (pronounced "Chumley") was born at Chorley, a small settlement approximately six miles south west of Nantwich, Cheshire near Cholmondeley, the eldest son of Joan Eyton and John Cholmeley, wealthy sheep farmers and land owners. See the heading "Tomb and Family Name", below, regarding the family name. While Richard was very young, his family moved to East Yorkshire, where his maternal grandfather held extensive estates.
Cholmeley was appointed Bailiff of York in 1492 and High Sheriff of Northumberland in 1495. In 1497, he served under Thomas Howard, Earl of Surrey to repel a Scots assault at Norham Castle, a stronghold of the Bishopric of Durham. For his service, Cholmeley was knighted in the field at Ayton by Lord Surrey as representative of the king. In the same year, he was appointed Lieutenant of Berwick upon Tweed and Governor of Kingston upon Hull. In 1499, Cholmeley and his younger brother Roger were appointed Constables of Pickering Castle, North Yorkshire and Stewards of the Honour and Foresters of the Royal Forest. While Roger settled in the constable's lodgings at the castle, Sir Richard purchased a small estate and house at nearby Thornton on the Hill (now part of Thornton-le-Dale). In 1506, Cholmeley was appointed Collector of the Great Custom in the Port of London.