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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45 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

    • Chris Cunningham heir to the the Earl

      Next time you see a Montgomery give him a nice kick to the jimmy’s and say that’s from Grand Da.

      • Joann

        My mother is a Cunningham on fathers side we have traced our history to this story, But Wait there is a twist my niece is marrying a Montgomery with the same history of Montgomery feud. We all live in America small small world that these two young people found each other in America.

        • Donna Montgomery

          My father’s side (Browning) hails from the Cunningham’s. I too married a Montgomery…LOL. I live in America too. Alexander Cunningham’s mother was a Montgomerie.

  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,


  3. Cindy Truelove

    Great writing!!! I knew of the fueds but this is the best piece I have read on it.
    Jim – Margaret Boyd was married to Alexander Montgomery… the chess set sounds amazing. Cindy

  4. Stuart Montgomery

    As a very young boy, my father, Hugh Montgomery, of Kilmarnock, told me about our historic Clan enemy – the Cunningham’s – & of Hugh Montgomery’s murder. By simple coincidence, the local bullies (near-by neighbours) who were the scourge of the area, were “the Cunningham’s” & to be avoided at all costs by “decent” local children.

    • J,loudon Cunningham

      Total crap,the Cunninghams were native to the area,thay took there name from the land going way back,before the french DeMontgomerys had even set foot in Scotland,thay put many a family into ruin!!

    • J,loudon Cunningham

      North Ayrshire was known as Cunningham,the old name Canega goes back before the Norse and Viking times,it takes its name from the celtic king of the time,some reserchers say it goes back to a offshot of the Dalriada race,theres more info than just your average clan internet sites if you do proper research and in later years the catholic Mongomoreys even added a “E” on to there name to make it sound more latinised when the Cunninghams joined the protesters about being ruled by Rome!!,as favours and backing from the catholic king thay sacked there way through north ayrshire but some familys stood up to them,hence 1528 Cunninghams burnt Eglington castle down ,one of many,the 2 familys had the longest family fued in british history,

    • Floyd M. Montgomery, P.O. Box 1456, Montgomery Texas 77356

      I wrote information on the Montgomery-Cunningham feud on 16 January 2019. I moved to Montgomery TX 6 months ago to set up a Montgomery family museum. I have almost 2,000 Montgomery items that I have collected over the past 30+ years. I have documents signed by Field Marshall Montgomery of WWII fame and General Richard Montgomery who was the first American General killed in the American Revolution at Quebec. One of my more interesting documents is by James Montgomery, 1st Baronet of Stanhope dated 1791. He is writing a friend about the King of France escaping from Paris. He did not escape for long as the Guilotine was used on him. You can contact me at Floyd M. Montgomery, P.O. Box 1456, Montgomery TX 77356

      • Joshua Cunningham

        where did you say your museum was? be a shame if something were to happen to it… 0.o lmao jk

  5. Chris Cunningham heir to the the Earl

    As a Cunningham I take offense to your display of Cunningham
    children being indecent. I would like you to say that to my face!

    • Francis Craig (me)

      Man up Chris ! Not only are the children indecent;it seem to me you are to and that’s to your face ! Be brave

  6. Lily Adamson

    Are ya’ll gonna start fightin’ again?
    Funny, in the greta American Classic, To Kill a Mockingbird, the bad folk are the Cunninghams….😁.
    Just teasing! I lived in Ayrshire for a spell and find it’s is amazing…very rich. Thank you for this article!

  7. Wesley D. Whitby

    Loved this. I’m a Cunningham through a grandmother. A number of years ago I found myself living on one side of a semidetached house – in the other, a Montgomery! We became and are still good friends, though we played many pranks on each other in those days. The shared crawlspace beneath the house was a much exploited design flaw. Don’t think he ever knew I was a Cunningham though. The Montgomerys have long since moved on and live in another town, but one of these days im going to need to sneak over and torch his “castle” on principle.

  8. Clayton Montgomery

    Kilwinning Abbey has the Montgomerie crest on stain glass, so would suspect that the Montgomeries held ownership at the end of the feud.

    • Floyd M. Montgomery, P.O. Box 1456, Montgomery Texas 77356

      I moved to Montgomery Texas a little over 6 months ago. I wrote information about the feud 16 January 2019. I have collected almost 2,000 Montgomery items over the last 30+ years and I hope to have a Montgomery Family Museum here by the end of summer. I was in Scotland almost 2 years 1983-1985, 2 months in 1987, and 6 months in 1989. Sadly, I have not been back since. I have documents signed by Field Marshall Montgomery of WWII fame and General Richard Montgomery who was the first American General killed in the American Revolution 31 Dec. 1775 a t Quebec. One of the more interesting documents is by Sir James Montgomery, 1st Baronet of Stanhope dated 1791. He is writing a friend about the escape of the King of France from Paris. He did not escape for long as he was beheaded. You can contact me at Floyd M. Montgomery, P.O. Box 1456, Montgomery TX 77356

      • J Douglas Montgomery

        I have traced my lineage to 1800 in Merriweather County south Georgia. Hezekiah M married Susanna Binns. I had heard that they came through Virginia but the building that held all the records burned and so much information was lost. Any additional information would be most welcome.

  9. Donald Cunningham

    Fascinating stuff.
    Have many Montgomery friends and never knew of this centuries-old feud until recently.

    We still share beers though…

  10. andy baird

    It’s not EGLINGton or ELLINGton. It’s Eglinton, just Eglinton. It’s originally a French name. Also in those days it was Cuningham with a single N and without an E at the end, and Montgomerie without a Y at the end. Your article is jumbled with variations of all spellings. Also the picture of “Eglington” Castle you display shows the final incarnation of the castle as rebuilt in 1802, long after the feud at the core of the article.

    • Floyd M. Montgomery, P.O. Box 1456, Montgomery Texas 77356

      Andy: I take it that you have some Montgomery ancestry in you. I wrote a comment 16 Jan. 2019. I moved to Montgomery Texas about 6 months ago. I have collected almost 2,000 Montgomery items over the last 30+ years and hope to have a Montgomery family museum here in Montgomery Texas by the end of summer. I have documents signed by the Field Marshall Montgomery of WWII fame and General Richard Montgomery who was the first American General killed in the American Revolution 31 Dec 1775 at Quebec. One of the more interesting documents is by James Montgomery first Baronet of Stanhope dated 1791. He is writing a friend about the escape of the King of France from Paris. He did not escape for long as he was beheaded. You can contact me at: Floyd M. Montgomery, P.O. Box 1456, Montgomery TX 77356

    • William Cunningham

      Kinda looks that way don’t it..I wonder if we will get a great assortment of recreational ATV trails as well..

      • William Alexander Cunningham

        Ha..I’m not the same William Cunningham as the first one in this thread
        I’m William Alexander Cunningham Located in Innisfil Ontario Canada

  11. Floyd M. Montgomery, P.O. Box 1456, Montgomery Texas 77356

    It was Sir Neil Montgomery of Lainshaw that was married to Elizabeth Cunningham of Aiket.. When she found out that the 4th Earl of Eglinton was going to visit Lainshaw, she notified her kinsmen that she would hang out a sheet from the upper window when the Earl had left in the morning. The Cunningham’s ambushed him about a mile from Lainshaw. The 4th Earl’s son became the 5th Earl of Eglinton. He died childless. Sir Neil Montgomerys son or grandson would have been next in line under normal circumstances because they were descended from the 1st Earl of Eglinton. The 5th Earl of Eglinton made arrangements with the King to disinherit Sir Neil’s family because his wife was the one that signaled her Cunningham kinsmen to ambush the 4th Earl of Eglinton. The Fifth Earl of Eglinton decided that a son of his fathers ( the 4th Earl of Eglinton) sister who was married to the Earl of Winton , a Seton, and who had 4 sons should become the 6th Earl of Eglinton. It took about 2 years for the King to approve. Sir Alexander Seton of Foulstruther changed his name to Montgomerie ending in “ie” not “y” and became the 6th Earl of Eglinton and thus the Montgomery Clan Chief. The first five Earl’s of Eglinton were Montgomery’s. The 19th Earl of Eglinton now resides in the U.S.A. Historically speaking, the Clan Montgomery won the feud with the Cunningham’s because we still have a Clan Chief. The last chief of the Cunninghams Earl of Glencairn died over 200 years ago. If you are interested in reading more about the Montgomery – Cunningham feud try: “The Lords of Cuningham” by William Robertson published in 1891.

    • RJ Montgomery

      That’s fascinating! Doing my ancestry and I found out I’m directly descended from the Lord of Lainshaw and his wife, Lady Cunningham. The disinheritance might explain why we moved to Ayr, became Covenanters, and then moved stateside.

  12. Bethany

    Wonderful article! I am a Cunningham descendant and am set to marry a Montgomery in Ayr on 19/8/19. He was born in Greenock, Scotland and came to the states at the age of 11. My grandfather (Cunningham) was also born in Scotland and came to the states when he was a teenager. So, we met in the US and and are going home to marry after 9 years together… Funny we should find eachother the way we have with such a history. Our relationship has had many ups and downs in those years and I can honestly say this tid bit about our families defines it nicely… But, life is wonderful and I believe our families are just tied at the core… Always destined to be together somehow…

    • Bethany

      Forgive me, my grandmother informed me that my great grand father was not born in Scotland, he was born here in the United States. West Virginia. I wanted to make sure I was accurate in my statement. Best to all.

  13. John Cuninghame

    You obviously are passionately interested in family history and I congratulate you on your enterprise in making your collection of Montgomery (Montgomerie) memorabilia. It so happens that one of my forebears married Penelope, daughter of Alexander Montgomery of Assloss. She was niece and heir to Walter Montgomery of Kirktonholm. Their son, Alexander Cuninghame, married Elizabeth, daughter of David Montgomery of Lainshaw. This all happened in the second half of the 18th century, almost a hundred years after the feud had come to an end. However there is one statement you make with which I take issue: “The Clan Montgomery won the feud with the Cunninghams because we still have a Clan Chief”. My opinion is that in fact both families lost, because both suffered much loss of life, frequent destruction of their live-stock and crops, and indeed the castles which were the seats of Eglington and Glencairn respectively were completely destroyed. While I respect your belief that there is no Cunningham Chief, I am pretty certain that the the present Lord Lyon would not agree with you.

  14. Trequela Matthews Davis

    Hi, my name is Alexandria Matthews, and I’m a new writer looking for a new story to tell when I had come upon the two feuding families of Clans Montgomery and Cunningham, right now I’m doing my own research on both Clans so that I can make my story a good read. I know that these two families are still even to this day feuding so I hope that my story when it’s finished could help them to put an to the Feuding once and for all.

  15. Christian Brænden

    I am one of many people in Norway who have a man called John Cunningham lived betwen 1575 and 1651 as one of my forfathers, Born in scotland but worked in service for king CHristian 4 of Denmark most of his life. First in the Navy. Later as Lensherre in Finnmark, Norway and died in his house in Denmark 1651. Are there some one in the Cunningham clan who have papers or know excact who are the parents and grand parents of my John Cunningham? Are there any family boks where i can find out more of the true lines back.

  16. Jeff Robinson

    My deceased mother was a Cunningham. I have in my possession an original bound copy of a booklet titled “History of the Cunningham Family” with the sub-title “Descendants of John Cunningham and his wife Elizabeth, who emigrated to America from the Scotch Settlement in the North of Ireland about the year 1748.” The booklet was published by the Press of Cunningham & Co. in Williamsport, PA in 1930. It was compiled by John Cunningham-4, Francis Cunningham-4 and Robert Cunningham-6. An introductory section about the Cunningham family in Scotland and Ireland before coming to America begins with a story about conflict between the Ireland and England during the reign of Queen Elizabeth and how that conflict escalated after James I came to the English Throne. Apparently as a result of a conspiracy against the King and his government by the Irish Earls of Tyrone, James I declared these earls to be outlaws and confiscated their estates which included about 200,000 acres of lands. James I, being both Scotch and Protestant, offered this land for settlement to Scotch Protestants provided they move to Ireland within four years. John Cunningham’s forbearers were among a group of Cunningham’s who lived in Ayrshire, Scotland and made the move to Ireland. I have no information about John Cunningham’s lineage or his life prior to his emigration to America except that his family was from Ayrshire and was part of the Cunningham’s involved in the Montgomery feud. John Cunningham died on July 4, 1776 at the age of 84. Apparently he was born in 1692. he would have been about 50 years old when he joined the thousands of Scotch Protestants leaving Ireland and coming to America to escape Irish persecution. If anyone doing ancestry research would benefit from the very extensive data in this booklet I will be pleased to provide either a digital or paper copy. Please feel free to contact me. The only cost will be a little conversation.

    • Jeff Robinson

      I noticed the statement “Your comment is awaiting moderation.” above my comment. Please explain what that means. I am wondering if I need to shorten the comment or if someone else is doing the moderation. Thank you for any help you might provide.

      • Greg Cunningham

        I descend through John’s son Paul>Alexander>Iredell>Alexander>Rufus>Ernest>John. I too would like to know more about John’s forbears. There was a Lt. Paul C’ham who married Rev. Andrew Stewart’s daughter of Donegore 1650’s who may have had some connection. There is another source to consider and that is the diary of my Paul’s granddaughter through his daughter Jean. Her name was Sarah C’ham Ramsay. She stated Paul was born on the Atlantic in 1735. As your pamphlet reads they came in 1748 when Paul’s brother Robert was 8, I know Lower Marsh Creek Church was founded 1748. I also know Paul fought under his captain James Houston with 3 of his own sons. John Houston,Jr came over in 1735 to PA and so did the Rev. Richard Sankey who preached at Lower Marsh Creek Church prior to Buffalo Church, all from North Ireland. Also, Paul came South with other PA family and neighbors including Caruths, McClungs and Whites who also lived in Knoxville, TN. Paul moved to Iredell NC area mid 1750’s then to the newly founded Knoxville, TN in 1797 where these mentioned apparently already lived. I am interested mainly in the Ireland and Scotland. Anything you may know would be greatly appreciated.


        Greg Cunningham

  17. Michael Kevin Parlow

    I’m a decendant of the montgomeries and shared this with my friend which is a cunningham . We are good I hope ,But if we cross a bridge together I’m sure going to be looking over my shoulder !

  18. Casey

    I am actually descended from both the Montgomerys and Cunninghams. My grandmother is a Cunningham, and my 12th great-grandfather is William Cunningham, 6th Earl of Glencairn. Funnily enough, my great-grandmother (my Cunningham grandma’s mother) has Montgomery ancestry. My 11th great-grandfather is Hugh Montgomery, 1st Viscount (1560-1636), who was the founder of the Ulster-Scots.


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