The inventory of Cromwell’s house at Austin Friars in Throngmorton Street records two portraits of Cromwell in the same room, presumably of different types. Cromwell is known to have sat to Holbein while he was Master of the Jewel House, circa 1532-4. The likeness then taken was most likely used for the celebrated portrait in the Frick Collection, New York, and adapted after Cromwell’s investiture with the Order of the Garter in 1537 for a miniature (London, National Portrait Gallery; S. Foister, Holbein & England, London, 2004, p. 104, fig. 110, ‘?Workshop’).

The present portrait is also adapted from the Holbein type, but showing a more sombre looking man. Variants of the present portrait are at Petworth, and also formerly in the collection of Lord Cunliffe (sold at Sotheby’s, London, 23 January 1946, lot 152) (see R. Strong, National Portrait Gallery: Tudor & Jacobean Portraits, London, 1969, p. 114, ’16th century workshop reproductions of varying size’).

The son of a cloth merchant, who was trained as a lawyer, Cromwell’s meteoric rise was owed initially to his conveyancing skills which proved indispensable to Cardinal Wolsey when selling off the dissolved monateries in the 1520s.

He went on to become Wolsey’s most senior and trusted advisor. Astutely acting as a go-between for the Cardinal and King Henry VIII during the divorce controversy, Cromwell managed to survive Wolsey’s disgrace and his abilities having come to the King’s attention, he secured a place on the King’s council in 1530. He subsequently took control of the supervision of the King’s legal and parliamentary affairs and became instrumental in the break from Rome, which asserted the royal supremacy over the church, enabling Henry’s marriage to Anne Boleyn.

He was rewarded by becoming principal secretary and chief minister 1534-36. Cromwell’s final fall from grace, which culminated in his execution in 1540, can be attributed to a number of set-backs, the final straw being his decisive part in Henry’s ill-conceived marriage negotiations with Anne of Cleves.