Essex grew his beard on his acclaimed expedition to Cadiz in 1596 which makes it possible to date his later portraits to the period 1596–1601. Gheeraerts, the leading portrait painter of this time, was responsible for all large-scale representations of Essex as a mature man within this period. The face pattern and pose are based on the full-length portrait now at Woburn Abbey. The carefully rendered details of the ribbon and Lesser George badge, and of the sword-belt, stand out against the white of Essex’s costume, a colour closely associated with Elizabeth I, the Virgin Queen.

Essex was a late favourite of Elizabeth, who sent him to crush rebellion in Ireland. He failed to do so, lost the queen's favour by unauthorized negotiations with the rebel Earl of Tyrone, was deprived of his lucrative offices and fell into public disgrace. In 1601, having deluded himself that Elizabeth needed rescuing from misguided counsellors he attempted a coup which was quickly thwarted and he was almost equally rapidly executed.