Painted circa 1657, this miniature of James, Duke of Monmouth would appear to be the earliest portrait of him, predating the unfinished image by Samuel Cooper in the Royal Collection (circa 1664/5). It is also the only portrait to have emerged of the young Duke in exile. Although only a young boy in this portrait, it is clear that this is a noble, if not quite royal, child. James’ pale blue velvet cloak is held with a heavily embroidered gold thread shoulder clasp, his hair shiny and coiffed, his tied cravat pristine. The private nature of this rare image is indicated by the surviving shagreen case, the hinged lid closed to prying eyes.

James, Duke of Monmouth was Charles II’s eldest son. He was born out of wedlock to Lucy Walters whilst Charles was in exile in Holland. Despite his illegitimacy, Monmouth was assured a life of preference and wealth, and the King treated him as his favourite. But from an early age Monmouth felt burdened by the disqualification of his birth, which ultimately led to his downfall and execution in 1685. Monmouth’s mother appears to have been Charles’ first mistress-in-exile - but was she also Charles’ wife? Rumours persisted from an early date that Lucy and Charles had secretly married. The evidence, a marriage contract, was said to be hidden in a ‘black box’. Samuel Pepys tells us of a rumour in 1662 that “young Crofts [Monmouth’s former name] is lawful son to the king, the king being married to his mother”. Although historical opinion has tended to dismiss the claim, for Monmouth the implication that he might be legitimate greatly affected his life.

The miniaturist David des Granges began his limning practice in the 1630s when he made his living through painting conventional portrait miniatures and responding to the growing demand for small versions of old master paintings. His family connections with Richard Gibson and his address in the heart of the limning community in Covent Garden stood him in good stead. Des Granges may have taken on some of Gibson’s less appealing commissions and he was in exactly the right place to obtain introductions to the nobles and connoisseurs surrounding the King. Eventually, he was formally employed by the future King Charles II, being appointed His Majesty’s Limner in Scotland in 1651.

Like most artists, des Granges needed to make a living during the volatile political situation which had culminated in the Civil War and led to the Interregnum. He joined a small group of artists who followed Charles into exile. Des Granges was almost certainly in The Hague, benefitting from the void left by Alexander Cooper’s departure and Peter Oliver’s death. His main employment was copying, into miniature form, oil portraits of Charles for distribution amongst Charles’ supporters. This fine and lively portrait of Charles’ son James, however, suggests a close and trusting relationship with his patron. As an artist from his native England, who had been part of the exiled court at least since the late 1640s, he was perhaps an obvious choice for such a potentially personal commission.

The suggested date of 1657 for the portrait is based partly on a comparison with the unfinished miniature painted by Samuel Cooper in circa 1664/5. James is markedly younger in the des Granges portrait, with the rounder face of childhood and the shorter curled hair more common in the pre-restoration period. In 1657 James was living with his mother in Brussels, where his father had established a small court, eeking out a miserable existence on hand-outs from sympathetic supporters. Lucy was similarly penniless, having been abandoned by her latest lover, Thomas Howard. It has not been possible to ascertain the provenance of this miniature, but if commissioned by Charles, it would have been a valuable visual reminder, as he saw little of his son between 1658 and 1660, not summoning him back to England until the summer of 1662. In 1658, after an initial bungled kidnap attempt, James was finally taken from his mother by Thomas Ross, a spymaster working for Charles, and removed to Paris. Having contracted venereal disease, Lucy perished in the same year at the age of 28. The portrait is unlikely to have been painted after James arrived in England in 1662, as by that date Samuel Cooper was firmly established as court limner (a position which was to become official in 1663) and would have been the obvious choice for such a commission.

Monmouth was always officially recognised as the King’s natural son. He was raised to a Dukedom in 1662, installed as a Knight of the Garter a year later and even granted use of the King’s coat of arms. But he was not entitled to any part of his father’s inheritance, and never officially placed in succession to the throne. By nature petulant and obstreperous, the possibility that Monmouth might one day be king only encouraged his occasionally reckless arrogance. His father therefore gave him a number of roles designed in part to keep him away from the danger of conspiracy. He spent much of his father’s reign in useful employment abroad, such as service in the French army in the 1660s, or the Royal Navy in its war against the Dutch in the 1670s.

At Charles’s death in 1685 Monmouth made the mistake of believing too much in his own claims to the throne, and overestimated the support on which he could rely in England. In June he landed in Dorset. His invasion force contained just eighty-three men, and the attempt to raise the West of England in a rising against James II was doomed to failure. Monmouth was defeated at the Battle of Sedgmoor and brought in supplication to his uncle. James, who had always been immune to the famous Monmouth charm, had little hesitation in ordering his execution. It is ironic that within three years James II was himself deposed, in a frenzy of unpopularity, by a foreigner, William of Orange, whose invasion force fired not a single shot. Monmouth had simply lacked patience.