An unusual portrait of a male sitter in civilian dress c.1800, identified as James Stephen(s) who is shown with a stylised stormy sea and a ship being wrecked in the background. Although he is described as ‘Captain’ James Stephen or Stephens of HMS Nassau which sunk off the coast of Holland 25 October 179, this cannot be so as the Nassau’s captain was Captain George Tripp, and there was no officer in the RN with this name. However, James Stephen(s) may have in some other way been associated with the Nassau, and chose to have his portrait painted with her wreck shown in the background. The clothes he is wearing are consistent with date of c.1800, as is his age, since the accompanying documents give his date of birth as 1766. What is particularly interesting is that James Stephens was registered as a Thames waterman in 1787 and 1800 as the accompanying documents show, and may also have become a city merchant. It is possible that he may have been, for some reason, on board the Nassau when she was wrecked and may have had the portrait painted as a commemoration of the event. Papers in the collection may suggest that he had reason to do work for the navy as there is also a receipt (20/11/1809) for two hundred pounds signed by the purser and captain of HMS La Fleche. It is likely that the papers which accompany the portrait (which include contemporary newspapers) may explain more about what Stephens’ connection was. Bequeathed by MIss IR Wolfe, great great great granddaughter of James Stephens, along with the papers mentioned above.