This picture was completed during the very early part of Holbein's second stay in England (1532-43), when he painted a series of eight portraits for a new category of patrons, the wealthy German Lutheran merchants of the Hanseatic League, whose guildhall was located in the London Steelyard, a complex of warehouses, offices and dwellings on the north bank of the Thames, where they resided and conducted their business. Holbein rented a house in nearby Maiden Lane and portrayed his clients in a range of styles, but always emphasising the importance of this emerging merchant class as it firmly took its place on the world stage.

The sitter, whose ring indicates the Wedigh family of Cologne, is, to the best of our knowledge, Hermann Wedigh III, when he was twenty-nine years old (died in 1560). The composition and pose are classically simple, and were possibly influenced by Titian, the celebrated Venetian painter (1488-1576). Please also refer to a similar portrait of 1536 depicting Derich Berck of Cologne (also in the Metropolitan Museum of Art), and a more detailed one of George Giese of Gdańsk of 1532, showing the merchant surrounded by exquisitely painted symbols of his trade.

There is a quotation in Latin on the sheet of paper protruding from the book on the table and it reads, "Truth breeds hatred" from the Roman comedy, "Andria", by Terence, which was popular among Renaissance Humanists (students of classical antiquity) and probably was the sitter's personal motto. The art historian, Ellis Waterhouse declares that Holbein's portraiture "remains unsurpassed for sureness and economy of statement, penetration into character, and a combined richness and purity of style.".