Hans Holbein the Younger traveled from Basel, Switzerland, to London in 1526, a year before painting this work. Bearing a letter of introduction from the philosopher Desiderius Erasmus, Holbein entered the intellectual circle of Thomas More and probably lived for a time with him in Chelsea.

A scholar and the author of Utopia, More was also a statesman. He served King Henry VIII as Privy Councilor for more than a decade and later became his Lord Chancellor, in 1529. More himself described his life around this time: “Most of my day is taken up by legal affairs, so at one moment I’m pleading a case, at another I’m hearing one, then I’m settling a dispute, and at another handing down a judgment. At the same time visits must be paid to somebody out of official obligation and to someone else on business matters; almost the whole day I’m out dealing with others, and what’s left I devote to my family, which leaves just nothing for myself—that is, for writing. Naturally when I get home I have to talk with my wife and chatter with the children, as well as speak to the servants. All this activity I count as part of my duty since it has to be done (and so it does unless you want to be a stranger in your own house)… Between all these activities that I’ve described, the days, the months and the years slip by.”

This portrait is a stunning evocation of More’s mind and character and a demonstration of Holbein's bravura illusionism. Just look at the stubble of beard and the seductive texture of the velvet sleeves. The prominent gold chain was an emblem of service to the king, its letters possibly standing for the motto "Souvent me souvien," which translates to “Think of me often.” Like the letter More holds in his right hand, this portrait may have been intended for a friend. It is first documented in the seventeenth century, in the palace of the Crescenzi family in Rome. A token of friendship, between the artist, the sitter, and maybe a third person, the portrait accomplishes what the humanist Leon Battista Alberti considered the ultimate goal of portraiture—to make the absent, present.  

More refused to subscribe to the Act of Supremacy, which recognized the king as the head of the Church of England. As a result, he was convicted of high treason, imprisoned in the Tower of London, and on July 6, 1535, beheaded—a punishment for which he is venerated as a martyr saint by the Catholic Church. The following year, Holbein became the king’s court painter.