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The 1745 Jacobite Rebellion came to a bloody end on 16 April 1746 at Culloden Muir near Inverness. Throughout the battle, Charles Edward Stuart (better known to posterity as Bonnie Prince Charlie) had been among his hungry and exhausted troops, shouting encouragement.

The prince’s prominence in the thick of it, surrounded by his horse guard, had made him a target for well-trained British-army gunners. Several officers nearby were wounded by the explosions, with one horse’s hind leg left hanging from the skin. Charles was unhurt, but his face and clothes were splattered with mud.

As the Jacobite lines collapsed, signalling a total rout, all observers agree that Charles, the 25-year-old Jacobite leader, left the battlefield accompanied by a small mounted guard and some of his senior advisers. But, beyond this, the prince’s escape has been a matter of great contention.

Colonel John William O’Sullivan, Charles’s most trusted friend and councillor, watched in dread as British Army cavalry moved across the field to cut off the prince’s retreat and implored him to retire immediately or be surrounded: “Well,” said the prince, “they won’t take me alive.”

William Home, a 14-year-old ensign at the time, later described how Charles was compelled to leave the battlefield “with the utmost reluctance, the bridle of his horse having been seized and forcibly turned about”, in order to save him and the cause he embodied, his dynasty’s restoration. The defeat at Culloden – the first suffered by the Jacobite army during the entire nine-month campaign – was, in itself, a disaster, but the capture or death of the Stuart prince would have been a catastrophe.

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Saving his skin

Others, however, far less sympathetic than O’Sullivan or Home, declared that, rather than standing firm with the intention to fight to the death, Charles refused point-blank to lead a last heroic charge. Worse still, he galloped off to save his own skin, to the terrible groans and screams of his injured and dying men.

Ever since he led a failed Jacobite rebellion against the British crown in 1745, Bonnie Prince Charlie has divided opinion. To his supporters, he was a courageous freedom fighter; to his detractors, a gutless popinjay. On this episode of the History Extra podcast, Jacqueline Riding considers the controversial prince’s life and legacy

At this moment, in anger and despair, the Jacobite cavalry commander, David Wemyss, Lord Elcho, shouted a bitter rebuke as the prince receded from view: “There you go for a damned cowardly Italian!” Sir Walter Scott certainly believed this version, noting it in his diary, as the information had come from Sir James Stewart Denham, Lord Elcho’s nephew.

Charles then, according to detractors, compounded his crimes by avoiding the chosen Jacobite gathering point at Ruthven, due south of Culloden, instead issuing a few days later, via note rather than in person, the notorious order: Every man for himself.

With these words, Charles destroyed any hope of rallying his troops to fight another day, in the process abandoning them to the retribution of the British Army commander-in-chief, William Augustus, Duke of Cumberland, and ushering in the violent pacification of the Highlands.

Charles, meanwhile, scuttled off to the west coast to catch the first ship back to France. The “Frightened Italian Bravo” – echoing Lord Elcho – versus Cumberland’s undaunted British hero became a familiar trope in anti-Jacobite prints published in the weeks, months and years following Culloden.

The dramatic variation in these recollections establishes more broadly the case for and against Charles Edward Stuart, which, to a large degree, remains with us still.

On the plus side, a brave, charismatic man, audacious to the point of recklessness, a Scottish hero (the Stuarts or Stewarts being the ancient Scottish royal dynasty) in the mould of William Wallace and the prince’s ancestor, Robert the Bruce – determined, against the odds, to try, try and try again.

This Charles Stuart lingers in the inscription on the 19th-century cairn at Culloden battlefield, dedicated to “the Gallant Highlanders who fought for Scotland & Prince Charlie”, and whose stone effigy, with its thousand-mile stare, stands atop the monument at Glenfinnan: the place where, in a thrilling moment early in the rising, Charles raised his standard to the wail of pipes.

For the prosecution, Charles is an emotionally distant and effete foreigner, indifferent to the suffering his rash restoration attempt was now unleashing on his followers. In the face of genuine danger, so this argument goes, he displayed shameful cowardice unbecoming of the ancient Scottish dynasty: a Stuart in name only, in fact, to those like Lord Elcho, barely Scottish at all.

This characterisation influenced Scott’s famous novel Waverley (1814), set during the rebellion and, more overtly still, his Tales of a Grandfather(1828–30), both of which, in turn, inspired John Pettie’s famous painting from c1892, Bonnie Prince Charlie Entering the Ballroom at Holyroodhouse.

Certainly, you can imagine Pettie’s popinjay prince, with his superior expression and penchant for Highland fancy dress, exiting the field at Culloden without a backward glance. This Charles Stuart makes a reappearance in Peter Watkin’s extraordinary film Culloden (1964), based on John Prebble’s account of 1961 and for whom Prebble acted as historical adviser. Here the gormless Charles feebly asserts his divine right to rule, even in the midst of defeat, with a bizarre pan-European accent. Diana Gabaldon’s bestselling Outlander novels and the equally successful TV series that derive from them have reinvigorated, to a degree, this particular idea of Bonnie Prince Charlie.

Georgian “usurpers”

As ever, both versions have elements based in fact. Charles was born in Rome on 20 December 1720 (according to the Julian calendar) at the Jacobite headquarters, the Palazzo del Re. His arrival rejuvenated the Jacobite cause as the first Stuart male, from the senior and Catholic branch, since the birth of his father, James Francis Edward in 1688.

From this circumstance springs the greatest myth concerning their supporters (or Jacobites), that they were predominantly Catholic, alongside the misconception that the movement was essentially Scottish and ‘nationalist’. In reality it was a broad coalition of different people and interests, from across the British Isles and beyond, for and against the Union of 1707, and as likely Anglican or Episcopalian Protestants as Roman Catholics.

The only thing uniting them all was the desire to remove the “usurpers” (as they described George of Hanover, who ascended the British throne as George I in 1714, and his brood), and restore the Stuart dynasty.

Charles’s home life was far from stable, with religion central to his parent’s increasingly fractious relationship. Both James Francis Edward and Maria Clementina Sobieska were staunch Roman Catholics, but unlike his Polish wife, James knew that his pronouncements on religious toleration, as one cornerstone of a restored Stuart monarchy in Protestant Great Britain, meant allowing some freedoms for non-Catholic courtiers and exiles at the Palazzo del Re, including a chapel for worship. Maria Clementina entered a convent in protest, enlisting the support of the pope in this damaging quarrel. The situation was only resolved on her death in 1735.

Aside from the emotional impact on the young Charles, this early experience seems to have distanced him from any strong allegiance to Catholicism. It also convinced him that his father’s determination to be the Catholic ruler of his dominions – not converting for the sake of his country, as his ancestor Henry IV of France had done – was one, if not the barrier to their restoration.

In a similar vein, by whom and how the Stuart heir apparent should be educated was also rife with religious tensions. A Roman Catholic, born and raised in the heart of Catholicism and whose lifestyle was sponsored by the pope, was an obvious focus for British government propaganda.

James eventually gave the vital role of the prince’s tutor to James Murray, Earl of Dunbar, a Scottish Protestant, and then hedged his bets by appointing Sir Thomas Sheridan, an Irish Catholic, as deputy. The ongoing wrangles damaged any hope that Charles would receive a rounded education fit for the leader of a military campaign and, if successful, the future king of Great Britain and Ireland.

There is no evidence that Charles received any formal training in military theory, considered standard among his peers. Nor did he actively expand (through reading, for example) his knowledge of the nations he was, he believed, destined to rule – beyond, that is, imbibing the partial and increasingly nostalgic reminiscences of the exiles resident at the Jacobite court and its environs.

The French author Charles de Brosses, after visiting the palazzo in 1739, observed that both Charles and his younger brother Henry Benedict (born 1725) “had but a mediocre wit, and are less polished than princes should be at their age”.

In support of this, Lord Elcho recalled that “Lord Dunbar is a man of the world and should have been able to give him [Charles] a better education, which he is accused of having neglected; Sir Thomas Sheridan is an ardent papist with no knowledge of how England is governed, and who holds the loftiest notions about the divine right of kings and absolute power.”

The notion that the British people in their entirety, oppressed by the tyranny of the ‘Elector of Hanover’, were simply awaiting the arrival of their rightful prince, a delusion Charles seems to have laboured under, has its origins here.

Perhaps more troubling, in regard to his readiness for any restoration attempt or, indeed, assuming his ‘rightful’ position as Prince of Wales, Charles appears to have been kept away from the inner-workings of the Jacobite operation in Rome until, finally, when almost 20 years old, he joined his father’s council. By this point, indulged by his loving but ill-advised parent, he had been abandoned for too long to his own inclinations and the advice and opinions of a small coterie of men, including his tutor Sheridan, which, as argued by Lord Elcho among others, would have a significant impact on his character, attitude and behaviour.

Charles’s natural buoyancy was countered by a suspicious and even depressive streak, which manifested itself during the campaign of 1745. His Scottish commanders, admittedly after Culloden, accused him of treating them throughout the campaign in an autocratic manner, expecting absolute obedience and loyalty rather than earning their devotion and respect. If challenged he would take offence and then fall back on his inner circle, including O’Sullivan and Sheridan, who naturally agreed with him. But it is hardly surprising, given his early life in Rome – when he was perpetually watched by British government spies and informers – that he relied heavily on individuals who had proved their loyalty to him personally.

Slim and elegant

Yet in some respects the Stuart prince was very accomplished. Through his passion for hunting he became a crack shot, an excellent horseman and had the stamina to take on the physical rigours of a military campaign. In other ways, too, Charles matched up to the ideal of a prince of the ‘ancien régime’. He was a talented musician, an elegant dancer and his physical appearance – auburn hair, dark brown eyes, tall and slim-built – certainly helped.

Such was Charles’s youthful appeal that supporters pondered on bypassing the world-weary father in preference for his handsome son. British government ministers were also regarding the young, rather than old ‘pretender’ as the one to watch.

Anyone who had been paying close attention to Charles could have predicted the events of 1745 to 1746. De Brosses made a very important observation regarding Charles’s life in Rome: the prince “feels deeply the oppressive character of his present position, and, should he not one day be relieved from that oppression, a want of enterprise will certainly not be the cause”. When, in early 1744, a French invasion in support of the Stuarts and headed by Charles failed, the prince, in pursuit of his destiny, spent the next year secretly organising a small military landing on the west coast of Scotland.

Marching into England

Although no one seems to have believed him, Charles had given some prominent Jacobites due warning, during a meeting the year before with John Murray of Broughton (his principal secretary during the campaign), that he would be “coming home” in the summer of 1745. Just prior to leaving France for the Western Isles, Charles wrote to Broughton: “I am now resolved to be as good as my word and to execute a resolution, which has never been a moment out of my thoughts, since I first took it in your presence.” Soon after, in a letter to his father who knew nothing of it, he reveals finally his plan to head up a rising “and so Conquer or Dye”.

Initially at least, the Stuart prince did not disappoint on his arrival in Scotland. Charles had to overcome significant resistance, even from traditionally pro-Stuart clan chiefs, which he did through perseverance, charm and using the ineffable power of royalty to appeal to the hearts, rather than the heads, of these loyal but understandably apprehensive Highlanders. The army crossed from Glenfinnan to Edinburgh, and then swatted away the British Army at the battle of Prestonpans on 21 September. It then marched through northern England, via Carlisle and Manchester, and arrived at Derby on 4 December 1745. The ease with which it achieved all this seemed to confirm that God and the British people were on Charles’s side.

Murray Pittock answers listener questions on the Jacobites, and their attempts to restore the Stuart dynasty to the throne, on this 'Everything you wanted to know' episode of the HistoryExtra podcast

All remained well while the Jacobite army was on a winning streak. Charles was the image of an inspiring leader, rising early, chairing his war council, drilling his men and marching proudly alongside them. But challenges lay ahead.

Unbeknown to the prince, his predominantly Scottish officers had already decided that the market town of Derby was the line in the sand: if the English Jacobites rose (at last) and the long-promised French invasion materialised, then they would march on to London. If this did not happen, then, with three armies now converging on them, a swift retreat back to Scotland, to consolidate their strong position there, was the only logical path. Charles was for London – come hell or high water.

In view of the forces mobilising against him, this attitude gives the lie to accusations that Charles was a coward. But it was not a little reckless. Politically, the prince’s instinct makes sense. Despite its size, the Jacobite army had succeeded, beyond the most optimistic supporter’s wildest dreams, achieving the reputation for invincibility in the process – a situation that could carry it all the way to London. What 6,000 men and boys would have done on arrival in the metropolis is another matter altogether.

In the event, Charles’s commanders won the argument. The prince took the retreat from Derby personally, as a profound blow to his authority and the Stuart cause itself. From then on, his behaviour is described as transformed from inspirational and vigorous, to sulky and obstructive. Until, that is, he reached Culloden (the battle that has proven such a source of contention as to his character and leadership). This last throw of the dice seems to have energised him once more.

Arguably the most famous episode of Charles’s entire life occurred after his flight from Culloden. Unable to find a French ship, the prince spent five months as a fugitive in the Western Highlands, which included his celebrated escape to Skye in a boat with Flora MacDonald. During these desperate months, moving from isle to isle and hut to hiding hole, the prince, with a £30,000 bounty on his head, was assisted by locals who – whether for or against the Stuarts – did not want the ignominy of the prince’s capture or death to occur while among them. Many, like Flora, assisted him in respect for their clan chiefs and, on a very human level, because they had sympathy for a vulnerable, hunted man.

It is here where the legend of ‘Bonnie Prince Charlie’, the lad born to be king and who will come again, began to take shape. This image was assisted by the obvious parallels between Charles’s current travails and that of his great-uncle and namesake Charles II – even down to the way in which both men evaded capture. The elder Charles famously hid in the Boscobel Oak after the royalist defeat at the battle of Worcester (1651), while the younger one concealed himself in a habitation called ‘Cluny’s Cage’, formed from a hawthorn bush on Ben Alder.

Hitched up skirts

At first, Charles complained bitterly of his discomfit, at one time wrapped in a plaid and groaning pathetically as he was attacked by midges, or moaning, as he recalled, about a diet of “mostely nothing else but Milck”, which caused “a moste violent Bludy flux”, only alleviated by large doses of brandy. And his escape with Flora MacDonald, dressed as her Irish maid ‘Betty Burke’, encouraged gleeful reporting in London of the prince’s effeminate, even transgressive nature.

Charles later described “Betty” as “the character C-s [Charles] was to assume”, as if he were at a masked ball, and playfully hitched up his skirts – to the horror of those who were risking their lives to conceal him. In this sense, the prince conformed to Horace Walpole’s sneering comment: “We know nothing certainly of the young pretender, but that he is concealed in Scotland, and devoured with distempers: I really wonder how an Italian constitution can have supported such rigours!”

However, after several months on the run, Charles, the seasoned huntsman, began to ease into his current circumstances. One observer, John Cameron, who met the prince late August 1746, over four months after Culloden, described him as “bare-footed, had an old black kilt on, a plaid, philapeg and waistcoat, a dirty shirt and”, most startling of all, “a long red beard, a gun in his hand, a pistol and durk by his side. He was very cheerful and in good health.”

Cameron conjured an image of a man at home in the rugged glory of the Highlands, about as far away from his pampered existence in Rome as it is possible to get. Even so, as the company sat down to eat, straight from the stewing-pot bubbling on the fire, the prince pulled out a silver spoon, rescued from his baggage after the battle, with which, without ceremony, he served himself.

A few weeks later, he and his protectors received news that a French ship had arrived at Borrodale. Before boarding, Charles turned to his companions and declared “my lads be in good spirits, it shall not be long before I shall be with you, and shall endeavour to make up for all the loss you have endured”. No doubt, Charles meant it. For, on arriving in France, he set about agitating for the men, money and arms needed to continue the fight.

But, even as the ship steered out on to the open sea – and before we get too carried away with the romance of it – one of his companions, John Macdonald, observed that the prince had most certainly left the Highlanders “in a worse state than he found us”.

As it turned out, the rebellion of 1745 was Charles’s finest hour, and the remaining four decades of his life can be summarised as a decline into despair, alcoholism and violence, particularly against his closest supporters, his mistresses and latterly his wife and daughter. The erratic behaviour and drunkenness meant that support for him drained away.

By the time his father died in 1766, even the pope and the French refused to acknowledge him as King Charles III. Without their support, the Jacobite cause was effectively dead. The prince resided at the Palazzo del Re, his birthplace, until his death in 1788. But back in the Highlands, like a ghostly Dorian Gray in reverse, the perpetual youth, Bonnie Prince Charlie, lingered on.

Jacqueline Riding is a historian and author whose books include Jacobites: A New History of the 45 Rebellion (Bloomsbury, 2016)


This content first appeared in the January 2021 issue of BBC History Magazine