Robert Gray was born in Taunton in 1570[1] and made his fortune in the City of London, where he became a Citizen and a member of the Worshipful Company of Merchant Taylors.

He owned a shop in Bread Street in the city, from which he traded in cloths purchased by him at provincial fairs which he then finished and dyed.

His business was successful and in 1635 his great wealth enabled him to build almshouses in his town of birth,[2] on East Street, next to the house in which he had been born.

[3] The initial building which Gray built in the parish of St Mary Magdalene in Taunton contained apartments for ten poor women, with a chapel, schoolroom, and a room for a reader, who acted as chaplain and schoolmaster.

In addition Gray gave an endowment to his almshouses of freehold land valued at £2,000, the profits of which were to be paid to the poor, with each receiving eight shillings a month.

[n 1][5] Although Gray had intended his Taunton almshouse to be managed by the Merchant Taylors' Company, hence their arms over one of the doorways, they refused to accept the trusteeship as they judged the distance from London was too great and his bequest allowed for no travel costs.