Early Life: Rome and the Stuart Court in Exile
Charles Edward Louis John Casimir Sylvester Severino Maria Stuart was born on 31 December 1720 in the Palazzo Muti in Rome, the palace granted to the Stuart court in exile by Pope Clement XI. He was the elder son of James Francis Edward Stuart — 'The Old Pretender', the man his supporters called James III of England and James VIII of Scotland — and his wife Maria Clementina Sobieski, granddaughter of the Polish-Lithuanian Commonwealth king John III Sobieski.
Charles was raised in the consciousness that he was a prince, the heir to three kingdoms, and that his family had been unjustly deprived of their throne by the events of 1688. The Stuart court in Rome maintained the forms and rituals of a royal court in exile. Charles was given an education appropriate to his status — languages, music, horsemanship, and the arts of war — but also grew up in a palace rather than a kingdom, surrounded by courtiers whose loyalty was to a cause that had already failed twice.
His father James was a melancholy, cautious figure who had led the failed 1715 and 1719 risings. His marriage to Maria Clementina was troubled — she retreated to a convent for a period in the 1720s amid disputes over the children's religious education. Charles and his younger brother Henry grew up in a household marked by piety, exile, and unfulfilled ambition.
Despite the constraints of his situation, Charles developed into a physically capable young man: an excellent horseman, an enthusiastic hunter, and reportedly charming in company. He learnt Italian, French, and English (though his spoken English was always somewhat accented), and showed an early taste for adventure that his father notably lacked. By his early twenties, Charles was chafing at the inaction of the Roman exile and desperate to prove himself.
The Road to Scotland: 1744–1745
The context for the 1745 Rising was European diplomacy. Britain and France were at war (the War of Austrian Succession), and France saw a Jacobite rising in Britain as a useful way to distract British military resources. In 1744, a major French invasion force was assembled at Dunkirk — a fleet of ships and an army intended to land in England and restore the Stuarts. Charles was in Paris, ready to lead the enterprise. The fleet sailed but was scattered by violent storms in the Channel. The enterprise collapsed before it began.
Undeterred, Charles determined to try again — this time without French support. He gathered what money and arms he could (famously, he sold his mother's ruby necklace to raise funds), hired two ships, and sailed for Scotland in July 1745. The larger of the ships, the Elisabeth, was badly damaged in an encounter with a British warship and forced to return to France — taking most of the arms and men that Charles had hoped to land with. Charles continued on the smaller Du Teillay with a small group of companions known as the 'Seven Men of Moidart'.
He landed on the island of Eriskay in the Outer Hebrides on 23 July 1745. The local chief, MacDonald of Boisdale, advised him to go home. Charles's response — reportedly — was that he had come home.
From Eriskay he sailed to the mainland, landing at Loch nan Uamh in Moidart on 25 July 1745. Gradually, clan chiefs came to meet him. Cameron of Lochiel — 'Gentle Lochiel', chief of Clan Cameron — was the pivotal figure. Lochiel had been doubtful and had tried to dissuade Charles from coming without French support. But Charles persuaded him, and Lochiel's commitment brought other chiefs into the rising.
The Standard at Glenfinnan: 19 August 1745
On 19 August 1745, Charles Edward Stuart arrived at Glenfinnan, at the head of Loch Shiel in the western Highlands. He had been waiting there with a small company when, to great relief, a column of around 700 Cameron and MacDonald clansmen appeared over the hill. The royal standard of the House of Stuart was raised by the Duke of Atholl (the Marquis of Tullibardine), and Charles was formally announced as Prince Regent on behalf of his father James III and VIII.
The assembled clans came from the Camerons of Lochiel, the MacDonalds of Clanranald, the MacDonalds of Keppoch, and smaller groups of other supporters. It was a modest beginning for a rising that would shake Britain.
This is the moment the Glenfinnan Monument commemorates.
The March South
The rising gained momentum rapidly. The Jacobite army marched eastward, gathering recruits. By mid-September 1745, Charles had entered Edinburgh — unopposed, the city gates having opened for him — and he established his court at Holyrood Palace, the traditional palace of the Kings of Scots.
The government army in Scotland, under Sir John Cope, had marched north to intercept the Jacobites but had avoided a battle in the Highlands. Cope transported his army by sea to Dunbar in East Lothian and marched west to confront the Jacobites near Edinburgh.
The two armies met at the Battle of Prestonpans on 21 September 1745. The Jacobite army launched a traditional Highland charge — a rapid advance under fire with broadswords drawn — against Cope's infantry at dawn. The government troops broke within minutes. Cope's entire army was routed. The battle was over in perhaps fifteen minutes. It was the Jacobites' greatest triumph.
With Edinburgh in his hands and the government army in Scotland destroyed, Charles held a glittering court at Holyrood for several weeks. Balls and entertainments were organised. He was the romantic prince, charming and confident, at the height of his fortunes. But the time was not used to consolidate — every week of delay allowed the British government to mobilise troops and resources.
In November 1745, the Jacobite army crossed the border into England.
The March to Derby and the Retreat
The Jacobite army marched south through Carlisle, Preston, and Manchester, gathering some English recruits but far fewer than Charles had hoped. The English Jacobites — real people, who had drunk the loyal toasts in private for decades — mostly did not come out. The army continued south, reaching Derby on 4 December 1745 — the closest the Jacobite army ever came to London, approximately 125 miles from the capital.
At a council of war in Derby, the Jacobite commanders debated whether to continue. Lord George Murray, the campaign's most capable general, argued for retreat. Intelligence suggested three British armies were converging. No significant English reinforcements had joined. The promised French landing had not materialised. Murray's arguments prevailed against Charles's passionate wish to press on.
The retreat from Derby — Black Friday as Charles called it — began on 6 December 1745. It was orderly at first. The army fell back through Manchester and Carlisle, fighting a rear-guard action at Clifton in Westmoreland on 18 December in which they beat off pursuing cavalry. They crossed back into Scotland in December 1745.
Charles was devastated by the decision to retreat. He never fully forgave his council, and his relationship with Lord George Murray — the brilliant military commander who had made the campaign militarily successful — became increasingly strained.
Falkirk and the End
Back in Scotland, the Jacobite army actually won another major battle. At Falkirk on 17 January 1746, the Jacobites defeated a government army under General Hawley in what would prove to be the last Jacobite battlefield victory. But the strategic situation was deteriorating. The Duke of Cumberland — the younger son of King George II, a capable and ruthless military commander — was marching north with a disciplined professional army.
The Jacobite army retreated northward into the Highlands. There were supply shortages, disputes among the commanders, and — fatally — a disastrous decision to fight a set-piece battle on ground entirely unsuitable for Highland tactics.
Culloden: 16 April 1746
The Battle of Culloden was fought on 16 April 1746 on Drummossie Moor, near Inverness. The Jacobite army of approximately 5,000 men — many exhausted from a failed night march — faced Cumberland's professional force of around 9,000 troops on open boggy ground. The terrain gave the Jacobites no advantage. The government artillery opened fire on the Jacobite line and devastated it before the Highland charge could reach the enemy.
The battle lasted under an hour. The Jacobite army was crushed. Perhaps 1,500–2,000 Jacobites were killed, including many of the Highland clan warriors who had followed Charles from Glenfinnan. The government forces suffered relatively few casualties.
Charles was persuaded to leave the field. He never returned. The Jacobite Rising of 1745 — the Forty-Five — was over.
The Flight After Culloden
What followed Culloden was an extraordinary five-month ordeal in the Highlands and Islands. With a £30,000 reward on his head — an enormous sum — Charles Edward Stuart became the most hunted man in Britain. Cumberland's forces scoured the Highlands, executing prisoners and burning townships suspected of having aided the rising.
Yet Charles was never betrayed. He was sheltered, fed, clothed, and moved from hiding place to hiding place by ordinary Highlanders — clanspeople whose families would face death if discovered — who remained loyal to the Stuart cause at extraordinary personal risk.
He hid in caves, in bothies, on open hillsides, in driving rain and biting Highland wind. He crossed between the islands of the Outer Hebrides — North Uist, Benbecula, South Uist — always just ahead of the government search parties. He was hungry, exhausted, and drinking far more brandy than was good for him.
The pivotal moment came through Flora MacDonald, a 24-year-old woman from South Uist. Despite the enormous danger, Flora agreed to help. She obtained a pass from her stepfather (a militia officer) for herself and an Irish servant named 'Betty Burke' to travel to the Isle of Skye. Charles was dressed in women's clothing and concealed in this fiction. On the night of 28-29 June 1746, they crossed by boat from Benbecula to Skye in rough weather — the 'boat song' Speed, Bonnie Boat commemorates this crossing, though the words were written much later. Charles spent a short time on Skye before moving on.
Eventually he made his way back to the mainland. On 19 September 1746 — exactly thirteen months after the standard was raised at Glenfinnan — Charles Edward Stuart boarded a French frigate at Loch nan Uamh (where he had first landed) and sailed for France. He never set foot in Scotland again.
Exile: Paris and Rome
In France, Charles was initially received as a hero. He lived in Paris, maintaining the posture of a prince in waiting. But the political winds had shifted. The Treaty of Aix-la-Chapelle in 1748 ended the War of Austrian Succession and committed France to expelling the Stuarts from French territory. Charles refused to leave — he had to be arrested by French soldiers and escorted to the border.
For the next two decades, Charles lived a peripatetic existence, moving around Europe — briefly in Avignon, then in various disguises in several countries. He became increasingly bitter about the failure of the Forty-Five, increasingly dependent on alcohol, and increasingly estranged from the Jacobite community in exile. He converted to Protestantism for a period in the 1750s, apparently hoping this would make an English restoration more politically feasible. It made him few friends.
His father James Francis Edward Stuart died in 1766. Charles assumed the Jacobite claim as Charles III. Pope Clement XIII recognised this claim, though it was widely understood to be symbolic.
In 1772, Charles married Louise of Stolberg-Gedern, a young German princess, in an arranged match designed to produce an heir for the Stuart claim. The marriage was unhappy. Louise found Charles — now in his fifties, prone to drunkenness and self-pity — a difficult husband. In 1780 she left him, eventually taking refuge with the sculptor Antonio Canova's patron, Count Vittorio Alfieri.
Charles had an illegitimate daughter, Charlotte, by his earlier long-term mistress Clementina Walkinshaw. In his old age he legitimised Charlotte, created her Duchess of Albany, and she came to Rome to care for him in his final years.
Death in Rome
Charles Edward Stuart died on 31 January 1788 at the Palazzo Muti in Rome — the same building where he had been born 67 years earlier. He died from complications of a stroke. His brother Henry Benedict Stuart, Cardinal of York (the last surviving legitimate male Stuart), was present at his death.
He was buried initially at Frascati, but his remains were later moved to St Peter's Basilica in Rome, where he lies alongside his father and brother in a monument designed by Antonio Canova. The monument is a place of quiet pilgrimage for Jacobite enthusiasts to this day.
Legacy
The story of Charles Edward Stuart has been endlessly romanticised in Scottish culture. The image of the gallant prince, the lost Highland cause, the faithful Highlanders who sheltered him at the risk of their lives — all of this fed a powerful mythology. Walter Scott's novels, the songs of Robert Burns, and a century of Highland romanticism transformed the Jacobite story into something more than history: a symbol of loyalty, lost causes, and a Scotland that had been defeated but never conquered in spirit.
The reality is more complicated. Charles was charismatic but erratic, brave but increasingly self-destructive. His decision to make the 1745 attempt without adequate French support was reckless. His reaction to the Derby council's decision to retreat was petulant. His later life was marked by alcoholism and self-pity.
Yet the image endures. At Glenfinnan, every year, the steam train crosses the viaduct close to where the standard was raised, and visitors from across the world stop and look at the monument at the head of Loch Shiel, and remember.