The Islayman at the Heart of the American War of Independence

It's not often that I have the chance to publish a lecture from Lord George Robertson on my blog. When Carl from the Ileach contacted me and asked if I would be interested to publish it, I didn't hesitate for a second (thanks very much Carl). What you'll find below is a fascinating account of a milkman's son from Islay who played a very important part in American History. Lord George Robertson delivered this fascinating lecture to a packed house at ICCI last week:

Major General Alexander McDougall
The Right Honourable the Lord Robertson of Port Ellen KT GCMG HonFRSE PC

Covering a whole wall of the old chapel of West Point Military Academy, the premier leadership training institution of the US army, are plaques commemorating the key military leaders of the American war of independence. In pride of place at the top, understandably, is that of General George Washington, Commander in Chief of the Continental Army and the first President of the United States. Immediately underneath that plaque is that of ‘Major General Alexander McDougall’ with his date of birth and his date of death 53 years later. Few people who see that plaque know that behind that simple name is the story of a remarkable man who was born at Portintruin, just outside of Port Ellen, on this island of Islay in 1732, two hundred and seventy nine years ago. “Alexander McDougall, a milkman’s son who helped to found a nation, blazed a trail across the American Revolutionary scene like a meteor”, said one history of that time.

There is here an amazing story, of a boy from Islay who in his twenties became the captain of two privateering warships, was afterwards a successful New York merchant, and, when the revolutionary tide started to flow was a key agitator and street leader whose provocative essay led to a jail term for libel and turned him into a hero in Britain’s 13 American colonies. He then became a soldier who rose to the highest rank in the American Army in just three years, serving under General George Washington. He was also a politician, an elected member of the first US Congress and was selected by that Congress to be the first US Minister of the Marine and was lastly a financier, first President of New York’s oldest Bank - the Bank of New York, which would be the first company registered on the New York Stock Exchange. He died at only 53 years of age in 1786.

After his death President George Washington called him a ‘pillar of the revolution’. So who was this man and why has he received so little notice for his starring role in the creation of the world’s most successful nation? Alexander McDougall’s father, Ranald, was a tenant farmer at Portintruin Farm, but also at Torodale and Nether Killean Farms in the parish of Kildalton and Oa on this island. Continue reading....

In 1738, when young Alexander was 6 years old (the same age as myself when our family left Islay) his family emigrated to America on the promises of a Captain Lachlan Campbell, promises of a better life which were to turn hollow when they got there. The McDougalls received some solid education at the church they attended at Ballynewtonmore Farm and they took to America good references from the local minister.

After a 3-4 month miserable journey by sea, Alick’s father rebelled against the man who had taken the 470 people from Islay, broke away and worked on a dairy farm, known as Beekman’s Pasture. He and the young Alick carried the pails of milk round the streets of Manhatten – then a pretty small place. (It is worth remembering there were not much more than a million people in the 13 colonies stretching from Georgia to Maine at that time).

McDougall went to sea at the age of 14. It was a rough and difficult life but unusually he thrived. At the age of 19 he took the long, difficult journey back to Islay (as we always do…..) and married a cousin, Nancy McDougall, daughter of the local Surveyor, Stephen McDougall. Although persuaded to stay he returned to America with his new wife.

Back at sea, at the age of 25 he Captained the ‘Tyger’, an 8 gun sloop with a crew of 62. Two years later he was Master of the 12 gun sloop ‘General Barrington’, with 80 of a crew. Ostensibly these were British warships fighting the French, but they also used that as an excuse to be privateers robbing ships of many nations and trading in slaves, molasses, tea and rum mainly from the Caribbean.

Off the back of this trading he became a prosperous New York businessman and quit the sea. He was wealthy. He owned land in and near New York, a tavern (a ‘slop-shop’) and a sloop called the ‘Shuyler’. He sent his sons to the Presbyterian College of New Jersey – now Princeton University. But “some would never accept him as a social equal”.

One of the Livingstons, part of the biggest Tory faction in New York, said this of him at the time, “Suitable to the savageness of his clime and disposition, goes forth a hungry Scotchman as a robber of mankind”. Another comment on him at the time was marginally less unkind, “A Scot whose heavy stuttering brogue identified his ancestry, he had broad shoulders, a muscular neck and a well proportioned head – all combing to give him a rugged appearance.”

He was known as a snappy, even flamboyant dresser and this was seen by the ruling classes as vulgar. He was dismissively referred to as Captain McDougall.

By the early 1760s, with McDougall in his early 30s discontent was rising at the attitude of the British government. The ‘Sons of Liberty’ were formed as a militant patriot body and McDougall was quickly seen as a street leader of the Sons.

In order to pay for the wars with the French and the Indians the British Parliament brought in the Stamp Act, the Mutiny Act and then, disastrously, the tax on Tea. The patriots’ slogan was ‘No taxation without representation’. The Boston Tea Party let a fuse. The New York tea party followed and McDougall was one of its principle organizers.

In 1770 McDougall wrote a pamphlet called ‘TO THE BETRAYED INHABITANTS OF THE CITY AND COLONY OF NEW YORK’. Distributed at night with a small boy hidden in a box who would jump out and paste it on walls, it provoked a disproportionate and counter-productive response. McDougall was arrested and charged with ‘False, seditious and infamous libel’ and, refusing to pay bail, was sent to the New Gaol of New York.

He served 5 months in jail becoming famous throughout the 13 colonies. He was visited by so many people that he had to schedule appointments, and eventually only in the afternoons, since he was writing so much. One commentator said it was more of a social event than a confinement.

On the 14th February, McDougall’s supporters arranged a celebration of the 45th day of the year. This number 45 was symbolic of the 45th edition of John Wilkes’ newspaper, the ‘North Briton’ which had led to the English MP’s own imprisonment for libel.

A Boston newspaper reported the celebration thus, “forty five gentlemen, cordial friends of American liberty, went in decent procession to the New York jail and dined with McDougall on 45 pounds of beefsteak, cut from bullocks 45 months old. The highlight was the arrival of 45 virgins who sang 45 songs”. Some serious questions, it has to be said, were raised about the veracity of the term ‘virgins’. One critic suggested they were all 45 years old.

In the history of West Point the author, Lt General Dave Richard Palmer, says that after prison (the charges were dropped), ‘wherever appeared that high forehead, accented by a receding hairline and puffy eyes, one could expect to hear hot words or hotter action from this Son of Liberty.


The resistance to Britain turned to war in the 1770s and McDougall was swift in joining the Continental (Revolutionary) Army.

In 1775 he was appointed Colonel of the First New York Infantry Regiment. He was 43. He was made a Brigadier General the following year, and the year after that Major General – the highest rank in the army, only Washington, the Commander in Chief being a full General. As a field commander, where he was happiest, he took part in the battles of Germantown, White Plains, and he was largely responsible for the successful war-saving retreat, Dunkirk-style after the Continental Army’s defeat at the Battle of Long Island.

McDougall was sent to command at West Point, a strategically vital point on the River Hudson, which flowed from the Canadian frontier down to New York. Referred to as the ‘Gibraltar of America’, it was vital to the war’s success. Had the British taken the Hudson they would have fatally divided the revolutionary forces. McDougall commanded West Point and the wild but hugely important Hudson Highlands for much of the war although he tried valiantly to get back to field command.

He supervised the building of the construction of the forts at West Point, the creation of a great Chain, a boom across the river, and he was posted there again to deal with the situation after Major General Benedict Arnold, a hero of the early war, defected to the British. Arnold whose name McDougall gave mischievously to the main fort at West Point, is commemorated with only one statue in America at the field of the battle of Saratoga. In an early battle he had been badly wounded in his leg. The statue is only of Arnold’s wounded leg. It says that that was the only patriotic part of him. His name is chiseled out of his plaque in West Point’s chapel.

The war was long, it was a war of attrition, brutal for the soldiers who were underfed, alternatively too hot or too cold and ill-paid and badly treated. The rest of the colonies however saw little fighting, fared relatively well and felt little sympathy for the poor souls fighting in the forests and on the battlefield for their freedom. This was to lead to a near mutiny in which McDougall played a major role - but that was later.

In 1778 the Americans signed a Treaty with the French against the British. It was a sadly premature moment of joy. In the history of West Point it was called a ‘wild, delicious, delirious time’.

The same history quotes contemporary records of McDougall, “who always displayed ‘much of the Scottish Character’ and was, when plied with wine ‘affable and facetious’ On such occasions he often described his ‘national peculiarities and family origin’ an act which never failed to convulse his audience in laughter. ‘Now gentlemen, you have got the history of Sawney McDougall, the milk-mon’s son.’

The joy was short lived and the French were reluctant to translate the Treaty into committing troops. Spirits plunged and in 1780 Alexander Hamilton, one of the moving forces of the Revolution and a founding father of the United States said this, “Our countrymen have all the folly of an ass and all the passivity of a sheep in their compositions. They are determined not to be free and they can neither be frightened, discouraged nor persuaded to change their resolution. If we are saved it will be France and Spain who will save us. I have the most pygmy-feeling at the idea, and I almost wish to hide my disgust in universal ruin”.

Two years later, and a year after he had been elected to the Continental Congress, McDougall had a furious fall-out, and clash of personalities with a fellow General, William Heath. (Familiar names to us at the time - Heath, Clinton, Thacher, Howe).

Heath had taken command of West Point and McDougall disagreed with his method of working; so he bitterly attacked him in public. Heath arrested McDougall and placed him on 7 charges, “conduct unmilitary and unbecoming an officer”. After a court marshal of 3 months where McDougall defended himself he was acquitted on 6 of the seven charges and reprimanded (gently) by Washington for calling Heath a ‘knave’. It did him little harm.

This was perhaps because McDougall was a very popular leader of men. There are many references to his conviviality. When Lord Cornwallis was defeated at Yorktown and surrendered his whole Royal army in October of 1781 there were wild celebrations when news two weeks later reached West Point. Dr Samuel Adams recorded in his diary “if our joy on the glorious occasion may be measured by the amount of liquor and wine we drank, it is beyond dispute that we were exceedingly glad”.

McDougall led the festivities. At dawn it is recorded that “after drinking a little coffee with a very hung-over Col Crane, the jubilant revelers took some wine and ‘cold collations’ with General McDougall”.

In his official biography, by Roger Champagne there is another hint about his leadership skills, “McDougall was direct and outspoken, too talkative perhaps, an affable drinking companion who made as much fun of himself as others, and who regularly invited his junior officers to share his table”.

Well, he did come from Islay...

Member of Congress

McDougall served in the Continental Congress as a delegate from New York from 1781-2 and again from 1784-5.

In 1781 the Congress decided that it could not continue to run its affairs by committee. It created four Departments of State – Treasury, Foreign Affairs, War (the Army) and Marine. McDougall was elected as the first ever Secretary of the Marine Department. He accepted, but with two conditions. One was that he be permitted to rejoin the field army for half the year and second, that he be allowed to retain his Major General’s rank (and, given his now poverty, salary). The congress declined his conditions but in his time in the post one of his tasks was to oversee to the appointment of John Paul Jones as first head of the US Navy. Jones, also to be an Admiral in the Russian Navy of Catherine the Great, came from the small Scottish town of Kirkcudbright in Galloway. One of his daring exploits as a marauding sea captain was to enter Lochindaal at this island and fire at Islay House. (Or so Tom Freidrich and Lady Clare Margadale tell me)

His conditions having been declined McDougall returned to West Point where he stayed in command on and off, until the end of the war when Washington took personal command. Even at that point Washington believed West Point was the most important location in the war.

However in 1783 the unpaid, underfed, undervalued troops who had won of the War to liberate America were in a state of real unrest and there was a serious risk of a military coup. McDougall was nominated to lead the delegation along with Alexander Hamilton to Philadelphia to plead with the Congress, of which he was a member, to pay the back-pay and treat the veterans with some justice. Their efforts averted the threatened coup and may well have saved the infant nation.

The British finally left New York, their last toe-hold on the continent, in 1783.

America’s proud commercial capital was a sad mess. 40% of houses had been destroyed. Refugees were everywhere and the economy was in ruins. Inflation was rampant, debt was huge and some desperate people were turning to violence.

Alexander Hamilton was galvanized into action. He proposed that a Bank be founded to lead the economic regeneration of New York. That bank was the Bank of New York, now the Bank of New York Mellon (who have given a modest donation to allow a memorial cairn to be erected in memory of McDougall at Portintruin). McDougall was nominated by Alexander Hamilton to be its first President. The bank was to be the first company quoted on the now mighty New York Stock Exchange.

McDougall did the job for a year, but being a man of restless action, resigned saying it was ‘too confining a life for me’. He went back to being a member of the New York Senate where he fought (successfully) for the separation of the church and state (the Church of England/Anglicans had opposed the patriots whereas the Presbyterians formed the basis of the Sons of Liberty.) and (unsuccessfully) against the issuing of paper money. He was carried into the Senate on a stretcher to vote on the latter issue.

Alexander McDougall, Islay-born but American by adoption, rebel by habit and inclination, a leader of men and a valiant fighter for liberty died in Nassau Street, New York City on June 10, 1786 at the age of only 53 years. He was buried in the graveyard of the Old Presbyterian Church. His memorial stone is situated prominently today on the wall of the First Presbyterian Church of New York in Greenwich Village and that stone will be replicated on the cairn to be erected on the hill overlooking his birthplace here in Islay.

We can now see why, after his death George Washington rightly called him a ‘pillar of the revolution’ and the New York Gazeteer said this of him on the day of his massively attended funeral; “Of strong intellect, prudent and sagacious in council, of deliberate courage in the field, he had equal claims as a soldier and a statesman.

While integrity, love of country, fortitude and ability continue to be esteemed, this sentiment will be the faithful guardian of his fame.”

The milkman’s son from Islay did well.

Tag: history mcdougall america general