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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. 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.

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.