English: This portrait of an unidentified twenty-eight-year-old man can be directly linked to a preparatory study (Royal Collection, Windsor Castle). The masterfully executed drawing was used for transfer, since its incised lines match the contours of the portrait precisely. Holbein left the painting’s execution to a workshop assistant.The inscription reveals that the sitter was twenty-eight years old in 1535. This has given rise to the theory proposed by Gray (1992) and Foister (2006) that he may be Sir Ralph Sadler (1507–1587), a diplomat and administrator whose biographical details indicate close connections with the court of Henry VIII. By the age of fourteen, Sadler resided in the house of Thomas Cromwell, in 1527 he became his secretary, and in 1535 he became clerk of the hanaper in chancery and built his own house in Hackney. Sadler was knighted in 1540 and appointed to the post of principal secretary of state to Henry. His long association with Cromwell led to his brief arrest on 17 January 1541 but six days later he attended a Privy Council meeting, having presumably cleared himself and resuming his post without further difficulties. He continued to serve Henry, as well as Edward VI and Elizabeth I, until his death at the age of eighty. The only other known likenesses of Sadler are his tomb effigy in Standon Church, Hertfordshire, and a full-length portrait showing him holding a hawk on his wrist, which survives only in a schematic copy. Although the MMA portrait and the tomb effigy display certain similarities, the difference of more than fifty years between the two images—one drawn and painted and the other a stone sculpture—makes a reliable determination of the sitter's identity impossible. For now, the identification as Sadler must remain hypothetical.

[2013; adapted from Ainsworth in Ainsworth and Waterman 2013]

Ainsworth (1989) concurs with Held (1949), Rowlands (1985), and Foister (2006) in rejecting the attribution to Holbein himself. Foister, observing that the hand is awkwardly small and narrow for the size of the man, ascribed the painting to the workshop.