‘Toothless’ Shane – the Outlaw Hero of County Tyrone

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The leap

Background to ‘Toothless’ Shane’s Exploits

In the late seventeenth century, the region around Dungannon, Omagh and Pomeroy in County Tyrone was the ‘hunting ground’ of local outlaw Shane Bernagh, the scourge of the authorities. His name and exploits have been immortalised in song, poetry and folk stories passed down through the generations.

The Donnellys

Shane Bernagh O’Donghaile (in English John Donnelly) is a descendant of the ancient Gaelic O’Donghaile clan of Ballydonnelly.

The Donnellys were part of the cenel nEoghain, making them kin to the O’Neills. The chief of the Donnelly’s was by tradition, the marshal of the O’Neill forces in the Province of Ulster. In 1603 Donnell O’Donnelly was with Hugh O’Neill at the Battle of Kinsale.

The Donnellys were of such high-standing, that they were the foster family for the O’Neill’s. At this time, it was common for high-ranking young men to grow up in the household of other leading families. This would forge strong alliances among the clans. Indeed, the famous Shane O’Neill was reared by the Donnellys.

Sir Toby Caulfield

Ballydonnelly (Baile-ui-Dongaile) in the townland of Lisnamonaghan, was the fort of the Donnelly’s and was in existence since at least 1531. However, in Plantation times Ballydonnelly and the surrounding 1,000 acres of land was ‘granted’ by the English King James 1 to Oxfordshire knight, Sir Toby Caulfield (Caulfeild) for services rendered during the Nine Years War. Between the years 1611-1619 Caulfield built a large and imposing house on the site. Caulfield was created Lord Charlemont in 1620.


“Castlecaulfeild” was founded by Sir Toby Caulfeild, father of the Charlemont family, and here in 1614 Sir Toby built a fine castle of which there are good remains to-day, picturesquely situated on a limestone rock which was once the site of the old fort of the Donnellys.

These Donnellys were dispossessed by James the First at the Plantation, and they waged incessant warfare for many years with the Caulfeilds to whom their stolen lands had been given”

Richard Hayward In Praise of Ulster 1946
Castle Caulfield
Castle Caulfield

Castle Caulfield

Castle Caufield was actually a substantial manor house. This is unusual as most of the English lords ‘granted’ Irish land at the time tended to construct the more easily defended tower house.

The grand manor house of Sir Toby Caulfield
The grand manor house of Sir Toby Caulfield

Above the doorway is the Caufield coat of arms. The house was built in a U-shape with arched doorways, fireplaces and mullioned windows (i.e. having one or more solid vertical pieces of stone, wood or metal between different parts of the window).

View of Castle Caulfield mullioned windows
View of Castle Caulfield mullioned windows
Castle Caulfield interior
Castle Caulfield interior
View of Castle Caulfield mullioned windows
View of Castle Caulfield mullioned windows
Interior arched doorway
Interior arched doorway
The Caulfield coat of arms
The Caulfield coat of arms

The Dutchman, Nicholas Pynnar, who was commissioned by the English monarch in 1619 to conduct a survey of the castles and fortifications of Ulster described Castle Caulfield as “the fairest building in the north”.

Castle Caulfield exterior view from its land
Castle Caulfield exterior view from its land
Castle Caulfield entrance
Castle Caulfield entrance
Castle Caulfield - a look inside
Castle Caulfield – a look inside

The 1641 Rebellion and its Aftermath

During the 1641 Rebellion, Shane’s father Patrick Modardha (i.e. ‘the Gloomy‘), fought with the army of Phelim O’Neill. Reputedly a distinguished soldier, he captured and burned Castle Caulfield to avenge the slight to the Donnelly clan.

Exterior view of Castle Caulfield damage
Exterior view of Castle Caulfield damage
Scotty taking a break
Scotty taking a break in the ruins

Under the English King Charles II, the Donnelly’s were dispossessed once again from their ancestral lands as Royal policy in Ireland continued to prioritise support for the Protestant ascendancy over the lives and welfare of the local population.

“It appeared that one interest or the other must suffer (Charles) thought it most for the good of the kingdom, advantage of the Crown, and security of his Government to conciliate the stronger and wealthier party at the expense of the poorer and weaker”

Carte 11 240
Toothless Shane - Armed & dangerous
Toothless Shane – Armed & dangerous

Shane Bernagh

Irish landowners were evicted and those who had lost their lands during the Cromwellian Wars, had their hopes of restoration dashed. Disinherited sons had little option but to turn to a life outside of the law.

“The O’Donnellys were dispossessed by King Charles II and this triggered off the oath of revenge by the clan. This was the cause of Shane Bernagh becoming a reparee”

Jim McCallen Stand and Deliver 1993

Toothless Shane

Shane O’Donnelly gained the nickname ‘Bernagh‘ (meaning ‘toothless) because it is claimed he never had any teeth!

It is said that his gums were as hard as iron, so tough that he could bite through gold and silver coins!

Despite his toothlessness, Shane also had a reputation as a ‘ladies’ man’. Even though he was married it is reported that he had frequent liaisons while on his travels throughout the county, even with many a high-class lady.

The Exploits of Shane Bernagh as a ‘Reparee’ (Highwayman)

Shane began his career with Redmond O’Hanlan (see related post below), but after his death gathered around him his own band of landless men with nothing to lose.

Their main hide-out was at Minamer Glen. They roamed the hills around Altmore, often swooping down on unsuspecting travellers on the Dungannon to Omagh road, usually well-to-do farmers returning from market with a full purse.

The outlaws in the forest
Shane Bernagh’s outlaws in the forest

Often Shane Bernagh stole horses and cattle, which he hid in the caves in the Altmore area. These caves are still known as ‘Bernagh’s Stables’. He is reputed to be one of the first reparees to dye horses to avoid identification. What is frequently mentioned about Shane is that he had a ‘certain way’ with horses and a great love for all animals.

The gang would rob the houses of wealthy Protestant landowners and demand protection money. According to Jim McCallen in his authorative book Stand and Deliver, Stories of Irish Highwaymen (1993), two of those who fell victim to this racket were Mr Evatt, High Sheriff of Monaghan and a farmer from Emyvale in the parish of Donagh, called Wright. The imposed fee for ‘protection’ was “£1, a quarter of beef and 5 stone of bread”. This would feed Shane’s men and also lends credence to the tale that Bernagh often divided his ill-gotten gains with the poor of the neighbourhood.

Shane was known for aiding the needy, especially those forced to become tenant farmers on tiny patches of the worst ground.

He further endeared himself to locals when he found and killed the priest-hunter who shot Fr McKenna while saying Mass on Christmas Day on the slopes of Slieve Beagh. Being a Catholic priest at this time meant there was a ‘price on your head’. Today a large Celtic Cross marks the Mass Rock where the Mass was ‘illegally celebrated’.

County Tyrone was particularly notorious for reparees, especially as many were aided by locals who were sympathetic with their plight and had been penalised themselves by the imposed and biased legal system.

Altmore, alias Barracktown

As Shane Bernagh’s reputation grew the authorities decided to erect a military barracks at Altmore to capture the outlaw dead or alive. A company of soldiers was stationed here by at least 1703. The barracks itself closed down in 1749, although it is interesting to note that in Griffiths Valuation (published 1847-1864), the area continued to be referred to as “Altmore, alias barracktown”. Even today the local road signs refer to the old military barracks.

Altmore Barracktown roadsign
Altmore / Barracktown roadsign

At this time the commander of the troops was Captain James Hamilton. He was known as being harsh and ruthless, both with his own men and with the locals. He was nicknamed, without affection, Black Jemmy Hamilton. That his ambition was more powerful than his loyalty is shown that while originally being a supporter of James II he switched sides to that of William of Orange to further his own interests. He was later created a viscount for his services to the Williamite cause.

The Hunt for the Outlaws

Shane Bernagh and his men continued to harass coaches, lonesome travellers and isolated farmhouses. His ‘guerrilla-type’ raids were impossible to predict. A network of sympathisers kept him informed of troop movements.

However, as more and more soldiers were deployed in the region, combing the vales and hills day and night, life was becoming ever more precarious for the outlaws.

The military set up outposts to try to trap the robbers and cut off their food supply. Villagers were constantly harassed and warned of dire consequences if they aided the reparees. The situation for Shane Bernagh was becoming desperate and the gang were taking more risks in order to survive.

The life of an outlaw in any time or country is not for the faint-hearted. No settled home or family life, separation from loved ones and the constant risk of betrayal due to the price on your head. Life as a reparee brought with it the near certainty of an early death. Only those with no faith in the law and government of the time would choose such an option, and the majority of Irish at his time had no respect for the ruling classes.

“The heathery gap where Reparee

Shane Barnagh, saw his brother die

On a summer’s day the dying sun

Stained its colours crimson;

So break the heart, Brish-mo-Cree

The whole landscape a manuscript

We had lost the skill to read,

A part of our past disinherited;

But fumbled, like a blind man,

Along the fingertips of instinct.

From A Lost Tradition by John Montague
The raid on the barracks
Shane’s raid on the barracks

The reparees were driven to more dangerous exploits. In one case, Shane Bernagh watched the soldiers leave Altmore on their daily patrol and then stole into the barracks and helped himself to supplies.

On another occasion when being chased by forces of the Crown, Bernagh on horseback jumped the width of a valley to escape. This is still known as Bernish Glen today.

Shane Bernagh making the jump
Shane Bernagh making the jump

One of the gang’s look-out posts, a rocky ledge on the outskirts of Cappagh is called ‘Shane Bernagh’s Chair’.

The view towards Shane Bernagh’s Chair
The view towards Shane Bernagh’s Chair

The Battle of Mullaghcarn Mountain

However, skill and luck can only last so long against an organised military force with overwhelming resources. Acting on ‘information received’ a company of English Redcoats descended on the slopes of Mullaghcarn Mountain in

The redcoats attack
The redcoats attack Shane

Bernagh’s gang were surrounded and a desperate gunbattle followed. It is said that when the outlaws ran out of ammunition, they used coat buttons for bullets.

Shane Bernagh Donnelly was shot dead.

The Tragic Aftermath

The victorious military cut off Shane’s head and sent it to the authorities to claim the reward money. His body was tossed into Loch an Albanaigh on the summit of Slieve Beagh on the borders of Counties Monaghan, Tyrone and Fermanagh. It was subsequently recovered by relatives.

Shane’s brother escaped and made his way under the cover of darkness to the cave where Shane’s wife and baby son were hidden. On news of his death, his wife, fearing reprisals, imprisonment and humiliation from the authorities killed the infant and then herself.

So ended the career of Shane ‘Toothless’ Donnelly. A lifestyle he would never have chosen but which he lived to the full. He is said to be the inspiration of George Sigerson’s ballad The Mountains of Pomeroy.

In addition, the ghostly presence of the tailor in Gerald Seymour’s book Journeyman Tailor (1989) set in 1970’s County Tyrone is a fictional representation of the man who betrayed Bernagh to the English dragoons.


Stories of the exploits of Shane Bernagh remain popular today.

He is remembered as a cunning man of great strength but also surprising agility. Tales of his physical prowess have become legendary – it is said that Shane could knock a bull unconscious with one punch!

Tales no doubt embellished over time in the telling but all portraying the admiration of the local people for their local hero.

Toothless Shane face-off with the bull
Toothless Shane – face-off with the bull

Related Post

Redmond O’Hanlon – A formidable 17th Century Outlaw

Count Redmond O'Hanlon
Redmond O’Hanlon (Reamonn O’hAnluain) was probably the most successful outlaw in Ireland in the seventeenth century.

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Des Donnelly · 4 November 2023 at 10:11 pm

I have to agree with Pat Holland, your grasp of geography in Tyrone is somewhat lacking, perhaps you may wish to confine yourself to the ‘alleys’ of Belfast. Since the Bernagh stables were located on Slieve Beagh and his body was recovered from Shane Bernagh’s Lough thereon I find the Mullaghcarn ‘story’ highly unlikely. Furthermore Shane is recorded as having lived in the townland of Stramacelroy, Knockatallon.

    P&P · 5 November 2023 at 6:07 pm

    My response would be the same as that given to Pat Holland i.e. that these legends tend to have differences in the telling based on different sources. We included a link below showing an alternative source for the Mullaghcarn story that you find “unlikely”. (It’s strange that you don’t find biting through metal with his gums or felling a bull with one punch unlikely).

    This is a hobby website with many stories told. We are always happy to update posts if alternative sources are quoted or we will note that there are different accounts. Feel free to send us an alternative information source and we’ll update the wording.

    As regards your suggestion that we “confine ourselves to Belfast alleys”, you could maybe acquaint yourself with manners. We’ll go where we want to.

Pat Holland · 17 October 2023 at 2:52 pm

Shane bernard was not killed at mullacarn ur reserch is crap

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