Hermann von Wedigh III (died 1560), a London Hanseatic merchant, engages our attention through Holbein’s central placing of his enlarged right eye, and arched eyebrow.

On the book cover are the initials HH, probably a rare instance of Holbein’s signature. One of the gilded clasps is open to allow the insertion of a sheet of paper. Its Latin inscription, ‘Truth breeds hatred‘, from the Roman poet Terence, may be an allusion to the truth of Protestantism, and the book may be a Bible; the Hanseatic merchants had imported Lutheran books into England.

Cyriacus Kale of Braunschweig holds letters addressed to him at the London Steelyard. The uppermost letter also includes his merchant’s mark of an arrow with crosses. Against the background is inscribed his age, 32, and the motto ‘Patient in all things’.

Holbein’s full-face portrait is lit to emphasise Kale’s bulging right eye and the scar on his chin. The black fur and damson coloured silk damask of his sleeves are sumptuously depicted, while the beautifully painted gloves are carefully placed to play against the curving designs of the sleeve.

Like Hermann von Wedigh (shown nearby), the sitter wears a ring bearing the von Wedigh family coat of arms.

In the early 1530s Holbein experimented with completely frontal portrait compositions, particularly in his portraits of Hanseatic merchants.

They perhaps wished to be shown full-face because their portraits were designed to be sent home as a complete record of their appearance. As in the portrait of his relative Hermann von Wedigh, Holbein has emphasised the size of the head and features and exaggerated the right eye.

On 31 May 1533 Anne Boleyn was welcomed into the City of London for her coronation procession with nine pageants along her route: costumed figures against staged backdrops recited poetry with classical themes composed by court poet John Leland and playwright Nicholas Udall.

The pageant organised by the Hanseatic merchants on the theme of Apollo and the muses is reflected in Holbein’s design, in which the elegantly grouped muses wear a mixture of classical and Tudor dress. As the musicians played, wine flowed from the fountain on Mount Parnassus, which was situated over an arch spanning Gracechurch Street.

This is Holbein’s only surviving drawing for the Hanseatic merchants’ Triumphs. The inscriptions hold the key to the symbolism of the procession, which both celebrates riches and suggests the qualities by which they may be acquired and maintained.

Plutus, or Riches, the old man seated high in the chariot to the right, is surrounded by men and women famous in antiquity for their association with riches. The driver holding the horses’ reins is reason (Ratio), with Fortune behind him. Female figures representing qualities such as liberality, good faith and equality drive the horses.

This engraving closely resembles Holbein’s preparatory drawing (shown to the right), without the changes to the figures evidently recorded by Vorsterman’s copy (shown nearby). However, it differs from that drawing in some respects, introducing figures on the far right, repositioning some inscriptions and adding others.

This engraving could have been based on a second, lost, preparatory drawing by Holbein. Other copyists placed the verses on the subject top left, and while this position may have been chosen by the engraver, he could also have had access to information taken directly from the finished paintings.

Holbein’s canvas paintings of the Triumphs of Riches and Poverty were made for the dining hall on the upper floor of the Hanseatic merchants’ residence in the London Steelyard. They were evidently intended to hang on the long and short walls of the hall.

Subsequently sold, they were destroyed by fire in 1752. These are the only copies which appear to record the colouring of the originals. The inscriptions on the copies make clear the moral: money is the source of sorrow, whether too much or too little.

As the drawing, ‘The Stone Thrower’ (shown to the right) makes clear, Holbein either owned or knew this print, adapting it for his own purpose. The subject is the suicide of Cleopatra, who is shown naked, applying a serpent to her breast.

Agostino Veneziano was an Italian engraver and draughtsman, who began his career in Venice, hence the origin of his name. In 1516 he travelled to Rome, where over the next ten years he produced numerous prints after Raphael, Michelangelo and Rosso Fiorentino.

One of the most important printmakers of the Renaissance, Raimondi helped to establish engraving as a reproductive medium. From about 1510 he was living and working in Rome, where he made many engravings after Raphael’s work, including Massacre of the Innocents and the Judgement of Paris (about 1517–20).

Holbein appears to have owned a number of his engravings after Raphael and used them as models for his own work.

The function of this exceptionally finished drawing is unclear. The presence of the column and the stones the woman holds have suggested the subject might be allegorical, perhaps an embodiment of Fortitude or Anger.

The careful description of the weight of the body reflects Holbein’s interest in movement, perspective and proportion, but the drawing appears to depend on the study and subtle adaptation of two Italian engravings displayed nearby, one inspiring the upper part of the body in reverse, one the lower.