[3] He encountered the pirate Edward England and was noted for reforming the administration of Madras Presidency on behalf of the British East India Company.

[5] Located in a prominent position (NS 236541, 628257) on the lands of Whiteside Farm overlooking Monkton this Corinthian style memorial was built between 1748 and 1750 for James Macrae by John Swan of Kilmaurs.

[15][16] Sometimes referred to as the 'Orangefield Family Burial ground',[17] during the restoration works in 2000 building contractors did discover human remains below the chamber within the monument.

'[20] The story's details are that a few years after his death several friends assembled at Orangefield House and after two days and two nights of drinking they made their way to Monkton Kirk and excavated several skulls and other bones from which they judged that the largest skull and longest shank bones would have belonged to their old friend and they duly lodged these within the monument that Shaw[21] and Cuthbertson[22] both refer to as a mausoleum.

William Johnson's 1828 map of Ayrshire records the Macrae Monument as an 'Obelisk' on the lands of Orangefield near Whiteside and shows it in the same form as it stands today.

[30] James Macrae is said to have loaned the City of Glasgow a considerable sum to help cover the levy imposed on them by Charles Edward Stuart, aka Bonnie Prince Charlie.