Sir Henry Guildford (1489–1532) was two years older than Henry, and was a close friend of the Prince. Guildford was one of Holbein’s earliest patrons and was portrayed by the artist in 1527, the year after he had been made a Knight of the Garter. The drawing is a study for a painted portrait on display in the State Apartments at Windsor. The finished painting shows Guildford holding the white staff of Comptroller of the Household, an office he had held since 1522.