Hans Holbein moved freely between the major powers of England at his peak, frequently persuading them to commission his services for portrait paintings. In some senses it would become fashionable to figure in their careers of artists such as this, particularly once they were known for having already worked with leading monarchs. Therefore, once Holbein had produced several portraits of Henry VIII, he would never be short of commissioned offers for the rest of his life.

Sir Thomas More was a speaker in the Houses of Parliament and one of the most powerful men in England at this time. Some of Holbein's connections suggested that he meet and greet More in order to spread his own influence and their meetings would later prove fruitful. Although the subject holds a particularly stern expression in this portrait, he is known to have been very pleased with the final result.

Thomas More himself was a highly versatile individual who at various points in his life would be a lawyer, author, philosopher and statesman. He remains most famous for his relationship with the ruling monarch of that period, Henry VIII. Once someone held favour with this strong leader, opportunities would be open to them right across English society.