THERE are so many “what if” moments in Scottish history that it is difficult to pick out one that is more important than any other.
That there are several “what if” moments attached to the 1745 Jacobite Rising alone shows just how Scotland’s history has often turned on a moment of decision or indecision, of luck and ill-fate, of glory… and of death.

What if in July 1745, Prince Charles Edward Stuart had stayed at home in Rome and not bothered to make the hazardous journey to a land he had never previously set foot in. After all, the great French invasion he was leading the previous year had been scattered by a storm, so he would have been well within his rights to take the setback as an ill omen and stayed at home. 

READ MORE: The saga of the first Jacobite rising in 1689

Yet believing utterly in his family’s right to the throne of the United Kingdom, and pledging also to end the Union of Parliaments just as his father had done in 1715, Charles arrived on Eriskay on July 23, 1745, carried there by a French 16-gun privateer called La Doutelle or Du Teillay. 

Contrary to the expectations of his Scottish supporters, there was no following French fleet. They had left France with just another man-of-war called Elisabeth, albeit a ship of 66 guns, but she had gone home after a battle with a Royal Navy ship, HMS Lion, had left more than a hundred men dead on both vessels, including the Elisabeth’s captain. The Elisabeth also took home most of the arms and supplies that had been provided by France for the Rising which, lest it be forgotten, was wanted by them as a distraction from the Continental War of the Austrian Succession in which the French army had just defeated the combined British, Dutch and Hanoverian armies under the command of the Duke of Cumberland, youngest son of King George II. Remember that name for later.   

La Doutelle sailed on from Eriskay to the mainland and dropped Charles and his companions plus the arms and funds on the north shore of Loch nan Uamh before it turned around at the Prince’s order and went home before the Royal Navy appeared.  Charles and his seven companions – the famous Seven Men of Moidart – stayed there at Borrodale House for a week as the Prince sent word to the clan chiefs that he would raise the Royal Standard of the Stuarts at Glenfinnan on Loch Shiel, where the monument stands to mark the spot.

Let’s deal with the seven companions. They were two Scots, an Englishman and four men of Irish origin, by name William Murray, the Marquess of Tullibardine, a Jacobite exile; Anaeas MacDonald, a Parisian banker; Colonel Francis Strickland, a sometime professional soldier; Sir John William O’Sullivan, a professional soldier; Sir Thomas Sheridan, a veteran of the ‘15; Sir John MacDonald or MacDonnell, a cavalry officer; and the Rev. George Kelly, a propagandist Protestant clergyman.  All were confirmed Jacobites and Sheridan in particular was close to the Prince as he had been his tutor. All would play a part in the Rising, though not all were successful.

Much more famous nowadays for the railway viaduct that featured in the Harry Potter films, Glenfinnan had earlier assumed an almost mythical place in Scottish history as the place where Charles raised the Stuart standard on August 19 having summoned the clans to begin the rising. It was not an easy thing to do – several clan chiefs urged that, without French troops, he would be better off home. 

Charles famously replied to one: “Sir I am coming home, and I will entertain no notion of returning to that place whence I came, for that I am persuaded that my faithful Highlanders will stand by me.”
He was right. The MacDonalds, the MacGregors, the Camerons and many more came to join the new army of the clans that swiftly marched south and occupied Perth. From there Charles wrote to his father: “Sir, since my landing everything has succeeded to me to my wishes. It has pleased God to prosper me hitherto even beyond my expectation. I have got together 3000 – and I am promised more – brave and determined men who are resolved to die or conquer with me.”

He had established a council of war featuring seasoned warriors and clan chiefs and they now urged swift action, not least because George II’s Government had placed a price on the Prince’s head – £30,000 or about £2m in today’s money.  

As rumours swept the country of an army of clansmen and French troops marching south,  Sir John Cope, commander-in-chief of the Government’s forces in Scotland, first tried to march north but on hearing that Charles had 3000 men under his command and his own troops barely numbered more than half that number, Cope marched off to Aberdeen and then went south by ship to Dunbar to wait for reinforcements.

By now a true soldier, Lord George Murray, son of the Duke of Atholl, had joined the Rising and was immediately made Lieutenant-General. He urged a march on Edinburgh and the Jacobites duly swept south towards the capital which responded by raising a militia, one of whom was the Rev Alexander Carlyle, famous later as Jupiter Carlyle, church leader and writer.

The city – but not the Castle – simply gave in, and its authorities fled to Berwick-upon-Tweed. In his capacity as Prince Regent, Charles entered the Palace of Holyroodhouse and proclaimed James VIII and III “King of Scotland, England, France and Ireland”. In line with his manifesto proclaimed at Glenfinnan, Charles spoke again of the “pretended union”.
For the benefit of those who do not know what he said and think he was some sort of a Unionist, here are the words of that Stuart manifesto, no doubt composed with the assistance of Sir Thomas Sheridan and the Rev. George Kelly. 

The National:

“We see a nation always famous for valour, and highly esteemed by the greatest of Foreign potentates, reduced to the condition of a province, under the specious pretence of an union with a more powerful neighbour. In consequence of this pretended union, grievous and unprecedented taxes have been laid on, and levied with severity in spite of all the representations that could be made to the contrary; and these have not failed to produce that poverty and decay of trade which were easily foreseen to be the necessary consequences of such oppressive measures…

“We farther declare that we will with all convenient speed call a free parliament; that by the advice and assistance of such an assembly, we may be enabled to repair the breaches caused by so long an usurpation, to redress all grievences, and to free our people from the unsupportable burden of the malt-tax, and all other hardships and impositions which have been the consequence of the pretended union; that so the nation may be restored to that honour, liberty, and independency, which it formerly enjoyed.”

Oh and for good measure, he promised freedom of religion, the advancement of trade, protection of liberty and property, the relief of the poor and peace. Not bad for a 24-year-old fop, as some called him.
Cope finally got his reinforcements but the fact is that most of the Government army had still not made it back from the defeat at Fontenoy in May. Cope knew his troops were second class but still decided to march to meet the Jacobites.

Huge mistake. Fully supplied and provisioned and with their own reinforcements joining every day, the Jacobite Army marched east to meet Cope at marshy plain of Prestonpans. They were nervous at first – Cope’s men had artillery and plentiful muskets, the clansmen just their pistols, broadswords, targes and dirks.  Cope had also chosen a strong position guarded by the marshes on one side.

A local man, Robert Anderson of Whitburgh, knew the terrain intimately and guided platoons of the Highlanders around the Government troops. On the morning of September 21, 1745, battle was joined. Cope’s artillery managed to fire a few rounds but Charles had seen action before as a teenager and was no coward. He himself ordered the charge and within minutes the clansmen had smashed through the Government lines. What had started as a battle between two forces of similar numbers became a complete rout, with Cope’s troops fleeing for their lives. Most cowardly were the dragoons which saw Charles and his cavalry coming and simply bolted.

Many lay dead on the battlefield and many more surrendered. In all about 200 Government men died that day or later from their wounds, and an astonishing 1600 were taken prisoner – that out of an army of 2500. Cope and his dragoons fled south and did not stop until the Border. The Jacobites lost less than 40 men killed and slightly more wounded. Cope also lost most of his munitions and the army’s pay chests which the clansmen gleefully looted.

Alexander Carlyle witnessed the flight of the Government troops and intervened to try and get some medical supplies. He wrote: “It was not long before we arrived at Cockenzie, where, under the protection of my guard, I had an opportunity of seeing this victorious army. In general they were of low stature and dirty, and of a contemptible appearance. The officers with whom I mixed were gentleman-like, and very civil to me, as I was on an errand of humanity. I was conducted to Locheil, who was polished and gentle, and who ordered a soldier to make all the inquiry he could about the medicine-chests of the dragoons. After an hour’s search, we returned without finding any of them, nor were they ever afterwards recovered. This view I had of the rebel army confirmed me in the prepossession that nothing but the weakest and most unaccountable bad conduct on our part could have possibly given them the victory. God forbid that Britain should ever again be in danger of being overrun by such a despicable enemy, for, at the best, the Highlanders were at that time but a raw militia, who were not cowards.” 

IT was a totally devastating victory and then came a real ‘what if’ moment. What if Charles had stayed in Edinburgh and contented himself with Scotland? He was advised to do and certainly enjoyed life in the Scottish capital – he held grand balls and had his portrait painted by the finest Scottish painter of the day, Allan Ramsay. That picture was lost for decades until being found in 2014 – it is now in the Scottish National Portrait Gallery. 

Down south, the news of Cope’s disaster occasioned the chief minister of George II, the Duke of Newcastle, to write to the King saying “Scotland has gone.” No doubt a Hanoverian Government would have invaded Scotland sooner or later, but what if Charles had said to them “end the Union of Parliaments and give me the throne of Scotland?” The course of the history of these islands might have been utterly different. Yet having been brought up to believe that his family were the monarchs of all Great Britain and Ireland, Charles felt he had no option but to invade England. He did wait a few weeks to gain reinforcements as some of the clansmen had gone home for the fast-approaching winter. 

In mid-October the Jacobite war council was split. Lord George Murray and his fellow Scots urged consolidation in Scotland, not least because they knew the Government in London was ordering full mobilisation. Charles wanted England’s throne, however, and the Prince won the argument, only to lose the war.