The present paintings are memorial portraits, presumably commissioned by Sir William Courtenay, 2nd Bt. and his wife Lady Anne Bertie of her principal ancestors. They are typical of the aspirations of the age when it was quite common to order pictures of one's ancestors if no other images of them existed. The only known contemporary portrait of Richard Bertie is a half length painting by an unknown sixteenth century English artist in the Ancaster collection at Grimsthorpe Castle, which is inscribed with the identity of the sitter upper left, as well as with his motto.

Richard Bertie was the founder of the wealth and power of the Bertie line (his father having been a master mason). This talented son joined the household of Sir Thomas Wriothesley, where he rapidly rose to prominence and became Gentleman Usher to Katherine, Duchess of Suffolk, the wife of Charles Brandon 1st Duke of Suffolk. She was Brandon's fourth wife –– his third having been Henry VIII's sister, Mary Tudor (1496-1533). Katherine was also Lady Willoughby De Eresby in her own right. On the Duke of Suffolk's death in 1553, Richard Bertie married the Duchess. Bertie and his wife were ardent Protestants and moved to Wessel in Germany to avoid persecution following the accession of Queen Mary, only returning to England after her death. Their son Peregrine inherited his mother's title, becoming Lord Willoughby De Eresby in 1573. His son became the 1st Earl of Lindsey in 1626.