Thomas Gainsborough painted the fourth Earl of Essex presenting a silver cup to Thomas Clutterbuck, a member of a prominent local family and also sheriff of the English county of Hertfordshire. In a letter to Clutterbuck that originally accompanied the cup, the Earl of Essex expressed his gratitude and regard for his friend:
It has long been my inclination to give you a small token of the regard I have for you, and hope this Cup which I desire y[ou]r acceptance of, will be agre[e]able to you, & that you will consider it as a small token, or proof how much I think myself indebted to you, & of an esteem which I shall always retain.
In 1784 the Earl of Essex commissioned the painting by Gainsborough to commemorate the presentation of the cup, which had actually taken place twelve years earlier. He then gave the painting to Clutterbuck. The two families maintained close ties throughout the nineteenth century, and the silver cup is still in the Clutterbuck family's possession. The painting, although it was paid for by the earl, also remained with the family until the Getty Museum purchased it in 1972.