Portrait of William Chiffinch

Another version of this can be found in the Dulwich Picture Gallery London

Chiffinch followed his older brother, Thomas, into service as a royal servant and was a page of the backstairs to Queen Catherine of Braganza in 1662. He succeeded to most of his brother's court offices upon Thomas' death in 1666, including being appointed Surveyor of the King's Pictures, page of the bedchamber and Keeper of the Privy Closet. Chiffinch became indispensable to Charles II and was known for his mastery of intrigue; he handled the payments to the king from France under the Secret Treaty of Dover.

His nefarious practices were mentioned in printed libels of the day such as

''Sir Edmonbury Godfrey's Ghost1, 1678:
It happened, in the twilight of the day,
As England's monarch in his closet lay,
And Chiffinch stepp'd to fetch the female prey.

The sitter was page to Charles II's bedchamber and keeper of the private closet. Delighting in intrigue of every kind, and gaining the confidence of courtiers and mistresses, Chiffinch was at the centre of the court's dissolute activities. His roles included smuggling in undesirables and mistresses, accepting bribes on behalf of the King and receiving the secret pension paid by the court of Louis XVI.

As the King's go-between he was known to all in the royal circle, including Pepys, with whom he sometimes held backstairs revels over wines and pickled herring or cold chickens. (Diary.)

He married Barbara Nunn, and his only daughter married Edmund Villiers, 1st Earl of Jersey. He was MP for Windsor 1685-87.

John Riley trained with the German portrait painter, Gilbert Soest (1605–81), and the English artist, Isaac Fuller (?1606–72); one of his earliest portraits is of William Chiffinch. He rose to prominence after the death of Lely in 1680, being appointed Painter and Picture Drawer in Ordinary to the king in 1681, and Principal Painter in Ordinary to William and Mary in 1689, jointly with Sir Godfrey Kneller.