Cunninghams and the Montgomeries – The Oldest Feud

For a long time in the fifteenth century and beyond the families of Cunninghams of Glancairn and the Montgomeries of Eglinton were deadly and bitter rivals, a bloody feud that makes Romeo and Juliet looks like child’s play.  It was described by John Lesie (exiled bishop of Ross who wrote the ‘Historie of Scotland’) as ‘the auldest fead hes bene of thame all”.

The Chief of the Montgomerys had become Bailie of Cunninghame in 1366.  During the fifteenth century both the chiefs of Clan Cunningham and Clan Montgomery became Lords of Parliament.  The Chief of Montgomery was made Lord Montgomery in 1444 and the Chief of Cunningham, ‘Lord Kilmaurs’ in 1450.  The Cunningham Chief was then further promoted to ‘Earl of Glencairn’ in 1503 and the Montgomery Chief  ’The Earl of Eglington’ in 1507.  Competition between the two families at this point was there, but very low key.

The feud began mostly over the Bailieship of the land of Cunninghame in 1425.  The Baillieship of Cunninghame had long been in the hands of the Cunninghams but in 1448 the Crown (King James II)  took it away from the Cunninghams and moved it into the hands of their neighbours, the Montgomerys.

Sir Alexander Montgomery was made Bailie (Chief Magistrate) of the King’s Barony (District) of Cunninghame, which had been held by Sir Robert Cunningham, who was married to Alexander’s sister.   Sir Robert believed that his position as Bailie was to be permanently held by the Cunninghams and not part of his wife’s dowry, as claimed by his brother-in-law.   So both the previous owner and the new owner were within the same family – this must have added fire to the feud.

Over what was a relatively minor matter their feud was to continue over centuries, despite legal judgements and government action.  It is arguably one of the longest and bloodiest feuds in Clan history.  Lasting from the mid 15th Century to the mid 17th Century.

Both the Montgomerys and the Cunninghams were powerful clans in the northern lowlands of Ayrshire, they were neighbours and the landscape they lived in had a lot to do with their feud and keeping it going.  The district is cut off by hills and water, to the south is the River Irvine, to the west the River Clyde, the north are the Kilbirnie Hills which form a natural barrier and in the east the hills that divide the district from Lanarkshire.

From 1425 onwards the feud between these Clans saw murders, assassinations, mounted troops raiding civilians killing many of them, the sacking of castles, burning of crops and fields.  The feud was to cause both families to erratically loose then gain fortunes as at one time one was winning then the next time they would loose.    This was all happening while Scotland and England were struggling for the throne.  The Cunninghams seemed to get the better of their rivals during the decade or so of fighting, but the Earl of Eglington(Montgomery) held great favour with James V and so benefited from the power that this gave them.

 Two Castles Destroyed


Eglington Castle

Both Clans had lavish castles that were only a few miles from each other; The Montgomeries of Eglinton had their castle on the banks of the Lugton and the Cuninghames hailed from the parish of Kilmaurs and Stevenston, their Castle was Kerelaw Castle.

Montgomeries of Eglington

Montgomeries of Eglington

With growing power came a corresponding growth of rivalry, until the jealousy and mistrust culminated in The Cunninghhams set fire to Kerelaw Castle in 1488. Although slow to take hold the floors were made of oak, as well as the beams and the furniture.  The fire spread gradually but surely from the basement to the turrets.  This was the end of Kerelaw Castle, it remains in ruins to this day.  Now the Cunninghams were angrier than ever and set on revenge.  They nursed their wrath for years.

The Earl of Glencairn retaliated by later burning down Eglinton Castle in 1528, the castle was rebuilt afterwards.


Kerelaw Castle

Kerelaw Castle



Opposing Sides in Battle and a Chief Slain
The two families were for a good while on opposite sides of the political fence and also religious; Cunningham was Protestant and Montgomery was Catholic.

The Montgomery’s and the Cunninghams were on opposing sides at the Battle of Sauchieburn (1488), with Hugh Montgomery among the victorious rebels.   Alexander Cunningham, 1st Earl of Glencairn was killed in battle as was the defeated James III.

In 1568 at the Battle of Langside the Montgomerys fought on the side of Mary Queen of Scots.  They were defeated and the Queen lost.  The Earl was declared guilty of treason by the Regency and imprisoned in Doune Castle. After being released he worked hard trying to secure safety and tolerance for other catholics.  His next two successors would follow him in supporting Mary Queen of Scots.  The Cunninghams were Protestants and did not.

During the upheavals of the 1560s and early 1570s  Alexander, 4th Earl of Glencairn (Cunningham) was among the most single-minded protestants of the Reformation.  In the Civil war he emerged as one of the core of the King’s men who overthrew Mary Queen of Scots.  The 3rd Earl of Eglington (Montgomery) was Catholic and until 1571 a Queen’s man, but in that year he and the other conservative Ayrshire lords changed sides and were thus able to end up on the winning side in 1573.  Finally the Cunninghams and the Montgomerys were on the same side.

The Murder of Hugh Montgomerie

Lainshaw Castle

Lainshaw Castle

In 1585 Hugh Montgomerie, 4th Earl of Eglinton was travelling to Stirling.  He had been ordered to attend court by the King.  The Earl was accompanied by a few domestic servants.  He stopped at Lainshaw Castle to dine with his close relative, a Montgomery, the Lord of Lainshaw, whose Lady was a Margaret Cunningham of Aiket Castle, with sisters married to John Cunningham of Corsehill and David Cunninghame of Robertland.

There was a plot to betray and kill the Earl, Hugh Montgomery, the story goes that he was followed from the castle and murdered.  It is believed that the Lady, who was a Cunningham or some say a servant who was a Cunningham climbed to the battlements after the meal to hang out a white table napkin and thereby signalling the troops who waited outside that the Earl was there.

Annick Ford

Annick Ford

Thirty Cunninghames attacked the Earl as he crossed Annick Ford and cut his servants to pieces; the Earl himself was dispatched with a single shot from the pistol of John Cunningham of Clonbeith Castle. His horse carried his dead body along the side of the river, still known as the ‘Weeping’, ‘Mourning’ or ‘Widows’ path.

Revenge on the Cunninghams  

A wave of bloody revenge swept over Cunninghame and elsewhere. In retribution the Cunningham relatives, friends and supporters were killed without mercy by the Montgomerys.

Aiket was killed near his home; Robertland and Corsehill escaped to Denmark. Clonbeith was traced to a house in Hamilton, possibly Hamilton Palace and hacked to pieces by Robert Montgomery and John Pollock. Robert also killed the Earl of Glencairn’s brother the Commendator of Kilwinning Abbey, Alexander of Montgreenan, thought to have instigated Hugh’s murder. He rode to Montgreenan and shot the Commendator at his own gate.

The Crown attempted to step in but failed.  At a parliamentary session in 1606, the Earls of Glencarin and Eglinton, along with their followers, fought each other from “seven till ten hours at night”.  Neither the King nor the Parliament was able to settle the dispute.  The crown had made repeated attempts to reconcile the families between 1595 and 1604.

Kilwinning Abbey

Kilwinning Abbey

Kilwinning Abbey

In 1570 the two Clan also clashed over control of Kilwinning Abbey. By this time the Montgomieries’ dominance of local patronage was almost complete; only the abbey remained outside of their jurisdiction.   The Earl of Glencairn’s  fourth earl’s son of his second marriage, Alexander Cunningham of Montgreenan, was appointed commendator of Kilwinning Abbey and contested the right of Hugh Montgomery, third earl of Eglinton, to act as bailie of the abbey’s regality.    Alexander was thought to be the instigator behind the plot to kill the 4th Earl of Ellington, Hugh Montgomery.

Interestingly there are tales of a Ley tunnel which is said to run rom Kilwinning Abbey, under the ‘Bean Yaird’, below the ‘Easter Chaumers’ and the ‘Leddy firs’, and then underneath the Garnock and on to the Montgomery’s Eglinton Castle.







The King Steps In … Again

James VI was made aware of the situation and he decided to intervene on behalf of the Earl of Eglinton.  A reason for this may have been that the Earl of Eglinton was a Roman Catholic and the Earl of Glencairn was suspected of heresy and, indeed, of being in league with Henry VIII, who was trying to gain domination of Scotland.

The government of King James VI of Scotland eventually managed to make the chiefs of the two clans shake hands. In 1661 Lord High Chancellor William Cunningham, 9th Earl of Glencairn, married Margaret Montgomery, daughter of Alexander, 6th Earl of Eglinton, drawing a line under the feud.



About Amanda Moffet

I run with Rodger Moffet. Live in Edinburgh and love travelling around Scotland gathering stories.

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2 thoughts on “Cunninghams and the Montgomeries – The Oldest Feud

  1. Patrick Cunningham

    Great history story, read a lot of Cunningham history but had not heard a good part of this,
    Patrick Cunningham

  2. Jim Arnold

    Hello Ms. Moffet,
    My name is Jim Arnold and I am making a chess set the theme of which is based on the feud between the Cunninghams and the Mongomery’s. In fact, a member of Clan Cunningham is the person commissioning me to do so. I am making the King’s Sir Robert Cunningham and Sir Alexander Mongomery. Can you tell me who Sir Alexander’s wife was? Also I am making Eglinton Castle and Kerelew Castles for the bishops…can you direct me to any pics of Kerelew Castle before it was burned?

    Thanks for your help! I’ll send you some pics of the finished project!
    Very Best Regards,



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