Cromwell was born in Putney circa 1485, and in his youth travelled to France, after which he entered the household of a wealthy banker called Francesco Frescobaldi, in Italy. Cromwell travelled to the Netherlands before returning to England circa 1516-1520 and marrying Elizabeth Wyckes (1489-1527). In England, he acted as a lawyer for various political figures and it was during this time that he first had contact with Cardinal Wolsey (1471-1530). By 1526, he had been appointed to Wolsey's council and remained in Henry VIII's favour after the Cardinal's execution in 1530. Cromwell was key in orchestrating Henry VIII's divorce from Catherine of Aragon in 1527 and enforcing the Act of Supremacy in 1534. Later political failures, however, including the marriage between the King and Anne of Cleves in 1538, soured relations and resulted in Cromwell's arrest and execution in 1540.
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, and while Cromwell is not shown wearing the collar of the Garter, his coat of arms (upper left) are encircled by the riband of the Order (bearing the moto 'Honi soit qui mal y pense'), indicating that it was executed in or after 1537. 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').