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1448, Sir Alexander Montgomery, Sir
Robert Cunningham's brother-in-law, was
made Bailie of Cunninghame, a title that
belonged to Sir Robert Cunningham. This
event sparked the bloody
Montgomery/Cunningham feud that lasted
213 years.
1458, Sir Alexander Cunningham was
rewarded for his support of King James II
(Stuart) against the Clan Douglas by
having his title Bailie of Cunninghame
restored, this enraging the
Montgomery’s.
1488, Sir Alexander Cunningham is made
1st Earl of Glencairn by royal charter,
and receives Drummond and Duchray in
Lennox for helping defeat the rebels at
Blackness (the rebels being an army of
King James III son James fighting to
overthrow his father). June 1488, Sir
Alexander Cunningham and King James III
were killed at the Battle of Sauchieburn.
The victorious son became King James IV
of Scotland.
Later in 1488, King James IV revoked
all titles given by his father over the
past few years. Sir Alexander
Cunningham's son and heir, Robert
Cunningham, lost his title of 2nd Earl of
Glencairn. He did however retain the
earlier title of 2nd Lord Kilmaurs. Also
in 1488, the Montgomery’s burned
down the Cunningham's Kerelaw Castle.
1498, Hugh of Eglinton, Lord
Montgomery, is made Bailie of
Cunninghame.
1499, Cuthbert Cunningham, 3rd Lord
Kilmaurs, leads the Clan in an attack on
Irvine.
1528, William Cunningham, 4th Earl of
Glencairn, lead an attack on the
Montgomery’s and burned their
Eglinton Castle (Irvine/Ayrshire).
The fifth Earl of Glencairn, a
Protestant reformer, fought against Mary
Queen of Scots forces. He was one of the
commanders at the Battle of Carbery Hill
where she surrendered in 1567. Glencairn
is said to have ordered the destruction
of the Chapel Royal at
Hollyrood/Edinburgh.
1586, the Cunningham-Montgomery feud
erupts after Hugh Montgomery, 4th Earl of
Eglinton, is murdered by
Cunningham’s. James Cunningham, 7th
Earl of Glencairn and 7th Lord Kilmaurs
is head of the clan at that time.
1661, William Cunningham, 9th Earl of
Glencairn, is made Lord High Chancellor
of Scotland for life. His marriage to
Margaret Montgomery, daughter of
Alexander, 6th Earl of Eglinton, ended
the Cunningham-Montgomery feud.
The Cunningham’s were among the
Scottish involved in the Plantation of
Ulster. Sir James Cunningham, who was
married to a daughter of the Earl of
Glencairn, was granted five thousand
acres in County Donegal. The name is now
among the seventy-five most common names
in Ulster.
The 9th Earl of Glencairn raised an
army in Scotland to fight for Charles II
in his bid to gain his father’s
throne. Somehow he managed to avoid
execution by Cromwell after the uprising
was crushed.
1699, Sir John Cunningham of
Caprington, a distinguished lawyer, was
created a Baronet of Nova Scotia by
Charles II.
Other prominent Cunningham’s
were Alexander Cunningham, an
eighteenth-century historical writer, who
was British envoy to Venice from 1715 to
1720.
Charles Cunningham was famous for his
historical paintings, some of which still
hang in the Hermitage Palace in St
Petersburg and Berlin.
Alan Cunningham, poet and writer, whom
many believe was only eclipsed by Robert
Burns, was born at Blackwood in
Dumfriesshire in 1784. His work was
supported by Sir Walter Scott who, on
Cunningham’s death in 1828,
provided for his two sons.
Caprington Castle was remodelled in
the 1780s and again in the 1830s. The
castle still remains in the Cunningham
family to this day.
The ruin of Kerlaw Castle has been
preserved as a tourist
attraction.
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