As tutor or administrator of James Sandilands of Calder, he entered into a dispute with the lawyer
John Graham of Hallyards, over the lands of Hallyards in
Midlothian. The elder Sandilands of Calder had granted Hallyards to his widow, who had married John Graham, but had also issued another disposition of the lands. Lord Home invited an English official,
John Carey, to come from Berwick to meet James VI at Dunglass in January 1595, but Carey refused to make the trip. James VI made a hunting trip to the area in February, planning to visit Dunglass,
Spott, Beil,
Waughton, and
Seton. On 13 or 14 February 1593 Sandilands shot John Graham dead in Leith Wynd in Edinburgh. Sandilands was in the company of the Duke of Lennox, going to play golf at Leith. It was said they had lured Graham to go Leith with an order for him to cross to Fife by ferry.
Alexander Stewart of Newtonleys, a follower of the Duke of Lennox was also killed, by a pistol shot to the head. His father, also called Alexander Stewart, was Captain of
Blackness. Calderwood said that Graham was finished off by Sir Alexander Stewart's French page in revenge for his master's death. Sandilands then went travelling in Italy, returning to London in September 1594. In January 1595 he fought with the
Master of Graham and his followers on Edinburgh's
Royal Mile, and was shot twice. George Lockhart of Ayr and
John Spottiswoode, the future
Archbishop of St Andrews came to his aid. On January 1595, to avenge his kinsman, the Master of Graham fought with him on the
Royal Mile at the Salt Tron. Sandilands' brother-in-law William Crauford, brother of the laird of Carse was killed. There were over 100 pistol shots and Sandilands was wounded. In the confusion, a rumour spread that King James was besieged in
Holyrood Palace. James VI made Sandilands and the Chancellor
John Graham, 3rd Earl of Montrose agree in November 1599. ==Catherine Carnegie==