This tiny item of men’s jewellery, less than 1.5 cm in diameter, was presented to the Trustees of Vaucluse House in 1964 by Sir Kenneth Whistler Street (1890-1972), former chief justice and lieutenant-governor of New South Wales. Street believed that the stud was one of three that had been given to colonial civil servant James Denham Pinnock (1810-1875) in 1839, and that it contained a strand of ‘Miss Wentworth’s hair’, held within a channel running through the coils of the ruby-eyed serpent. The gold stud itself is highly symbolic with the serpent representing undying love and the rubies standing for passion. The inclusion of a thread of hair makes this an emotionally charged item of jewellery. And that raises a question about the identity of ‘Miss Wentworth’ and her connection to Mr Pinnock. ‘Miss Wentworth’ was probably one of the daughters of D’Arcy Wentworth (1762-1827), the founder of the Wentworth dynasty in Australia, but the rest of the story is, alas, long since lost.