Thought to be by the French portraitist François de Troy (1645-1730), this half-length portrait shows the young Catholic claimant to the English throne, Prince James Francis Edward Stuart, pointing towards a group of ships at sea. Commissioned in exile from the chateau Saint-Germain-en-Laye, outside Paris, this gesture alludes to James' Jacobite title as 'the king over the water', and promises that he will cross the Channel to claim back the throne. It was probably intended for circulation among loyal Jacobites in Europe and at home.

However, since possession of Jacobite portraits in England, Scotland and Ireland was potentially treasonous, De Troy relies on small visual cues to convey his meaning. Most importantly, James lacks a crown or other royal regalia; his legitimacy is affirmed instead by the blue sash and Great George of the Order of the Garter worn over his jacket. His red coat resembles the one worn by the seventeenth-century English army – a potential harbinger of war – but his lace cravat, cuffs and decorative trim undermine this militaristic edge. Meanwhile, although James' gesture across the sea is here used as a claim on the English throne, it also echoes the composition of de Troy's 1683 portrait of James' cousin, the comte de Toulouse (1678-1737), as the five-year old Grand Admiral of France (Agen, Musée des Beaux-Arts). De Troy was a favourite court painter both to the Stuarts and to Louis XIV, and the visual connection between these portraits demonstrates the close relationship between the exiled Stuarts and the French artistic community at Versailles.

There are several known portraits of James Stuart pointing out to sea: de Troy's pupil and studio assistant Alexis-Simon Belle (1674-1734) painted a full-length version of this motif in 1703 (Scots College, Paris); another version by De Troy from 1704 is now at Parham House, Sussex. However, the age of the sitter in the Royal Collection portrait suggests a slightly earlier date than either of these versions, perhaps closer to 1701-2, when the thirteen-year-old prince had just claimed the throne after the death of his father, James II. This would place the portrait around the same time as another Royal Collection portrait from De Troy's studio, Prince James Francis Edward Stuart in Armour (RCIN 401250), and shortly after the Act of Succession of 1701. This specifically excluded the Catholic Stuart line from the English throne, and from this point onwards Jacobite portraits often took on an underlying militaristic tone. However, this remained implicit until 1714, when James II's elder daughter Queen Anne died and the throne passed to the Hanoverian George I; from this point on, 'James III' is often shown with the British crown.

Prince James Francis Edward Stuart (1688-1766) was the only son of the Catholic King James II and VII of England and Scotland. In 1688, the Protestant-led 'Glorious Revolution' dethroned the king and replaced him with his Protestant daughter, Mary (1662-1694), and her husband William of Orange (1650-1702). Prince James and his father and mother went into exile at the Château Saint-Germain-en-Laye, under the protection of Louis XIV. Later known as the 'Old Pretender', James participated in several unsuccessful plots to reclaim the English throne. In 1712, he left France to establish a court in Rome, where he married Maria Clementina Sobieska (1702-1735). He had two sons: Charles (1720-1788) and Henry (1725-1807), but was never to see a Stuart restoration; the male line died with Henry Stuart in 1807.