Of these clashes and quarrels, their feud with local family the
Montgtomeries produced several high-profile casualities on both
sides. In 1484, James, the 2nd Lord Boyd was killed alongside Hugh
Montgomerie, allegedly so the Boyds would never come to rule
Scotland. Some 40 years later, revenge was served after the
4th Lord Boyd slew Patrick Montgomerie in 1523.
Thereafter a tenuous peace bond was reached in 1530, with the
Montgomeries paying 2000 marks in restitution to the Boyds for the
original murder of James, the 2ndLord Boyd. However,
this peace did not last, despite the 4th Lord Boyds
daughter, Margaret, being married to a Montgomery. The Montgomery
feud was restarted in 1547 after Sir Neil Montgomerie was killed on
the streets of Irvine, and was ended when the
4th Lord Boyd was himself slain by Hugh
Montgomeries and his son, another Robert, ascended to become the
5th Lord Boyd. On ascension to his title, the
5th Lord Boyd again brokered peace with the
Montgomeries. His daughter Helen married Hugh Montgomerie c. 1560
and peace was finally reached in 1561.
Later, on succession of his title, his son, the
5th Lord Boyd gained prominence for his support of
John Knox and religious reform. However, not forgetting the service
done in reinstating Boyd estates, the Boyds changed sides to
support Mary Queen of Scots. The 5thLord Boyd became her
trusted advisor and accompanied her at the Battle of Langside. He
also managed her affairs while imprisoned by Elizabeth I of
England.
In the middle of this feud, the tenure of Dean Castle was also
changing hands. Following the exile and execution of Boyd members
after the Regency, the lands and property of the family were
confiscated by the Crown. On the marriage of James IV to Margaret
Tudor, older sister to Henry VIII of England, the new Queen was
gifted lands in Kilmarnock, including Dean Castle. However, she
rented the Castle and estate back to the Boyds for 600 marks a
year, and after her death in 1541, the estates and honours that
were stripped from his grandfather, the 1st Lord
Boyd, were reinstated sometimes after by regents for the infant
Queen Mary.