In my research on Osborne I found no connection between Osborne and the Soviets but I have a theory, that I admit is not founded on any tangible evidence, it is circumstantial at best, that Osborne may have had a connection to British intelligence. His last posting was in the British army was in Bermuda, which was at that time a British colony. Could he have been recruited there to do intelligence work for the British? He left the army in June 1914 but a travel document that I found indicated that he did not depart for the US until August 1914. By that time Britain was at war and Osborne, who had spent almost 8 years in the army was going to the US. Did he spend his last 2 months in Bermuda preparing for a new career as a spy for the British? I found a newspaper article in a Knoxville TN newspaper dated 1939, that said that he had made 14 trips to Bermuda. Why so many trips, was he reporting to his intelligence bosses in Bermuda?
Another interesting connection to intelligence matters could be derived from Osborne's British army record, his lectures in the US about life in India and Britain's interest in Indian nationalist movements operating in Canada and the US. During world war one Indian nationalists were trying to free India from the grips of British rule. Keeping India under its heel was especially important for Britain at this time because they needed India's resources to fight Germany. Britain ran a spy network in both Canada and the US on the west coast of both countries. Osborne often lectured on life in India and he could have based these lectures on his time in India when he was in the army. Could this have been a cover for obtaining information or making connections with people involved in these nationalist movements? I do not have any evidence that places him on the west coast of North America but there are large gaps in his timeline that are not accounted for. More work needs to be done to confirm if he was working for the British but if I had to choose between him being a Soviet or British spy, I would opt for the British.