Early Life and Career
Scotland was born in England to Scottish parents from Perthshire. His father was a railway engineer. He came from a family of nine children, three girls and six boys. He left school at the age of fourteen, worked as an office boy at a tea merchant's in Mincing Lane, London and then sailed to Australia before returning to England, where he worked in a London grocery business.
In his 1957 memoir The London Cage, Scotland wrote, "Perhaps because I had a variety of uncles, aunts and other relatives living abroad, my mind was focussed from an early age on the notion of a career overseas, and before I was twenty this compulsive travel urge was again asserting itself."
He travelled to South Africa with the intent of joining the British Army, as his brother was serving there and promised to get him in his unit. However, the Boer War had just ended by the time of his arrival. He then worked for an insurance company before returning to the grocery and provisions trade. He lived in the town of Ramonsdrift, at the border between South Africa and German South-West Africa. German forces became his chief customers, and he learned to speak German fluently.
At the invitation of a German officer, Scotland joined the German Army as "Schottland". In London Cage he says he took part in "several battles" with the Khoikhoi, then engaged in an uprising against German rulers of South-West Africa. He served in the German army from 1903 to 1907.
Upon return to Cape Town, Scotland was appointed General Manager of the government trading post at Ramonsdrift by Dr. L.S. Jameson, premier of the Cape Colony. The appointment made Scotland influential with British, German and Khoikhoi forces, and he became involved in cease-fire talks with the Khoikhoi leader Johannes Christian. Scotland was awarded the Order of the Red Eagle for his services.
During that time, Scotland began unofficially reporting German manpower and other information to British intelligence in Cape Town "and to General Smuts' agents on their periodic visits to me in my bushland commercial headquarters."
Over time, the Germans became suspicious of him, but no action was taken and he continues his work for both side until 1914, when he was imprisoned by the Germans on suspicion of espionage. He was interned in the prison at Windhoek until 6 July 1915, when the area was captured by British Empire troops. He returned to England upon his release. Following his return he launched an unsuccessful court case in the King's Bench Division of the High Court of Justice, attempting to recover the salary that had been withheld by his employer, South African Territories (Limited) whilst he was interned.
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