Numismatist Tom May gave a brief history of MacGregor and his business in his article, 'Token Issuers of George Street' (May, 1988). James MacGregor's first business opened in 1855 at 464 Elizabeth Street. This location, between Albion and Devonshire Streets, was adjacent to the Central Railway station. In 1861 he moved to 204 Pitt Street, between King and Hunter Streets.

His success led him to move to 320 George Street in 1865, and he continued to do well in business for another couple of years. Unfortunately, the tokens he commissioned from Heaton and Sons, Birmingham, arrived in 1868, the same year the N.S.W. Government decided to demonetise tokens. This issue consequently holds the doubtful honour of being the last in N.S.W. and the entire issue is thought to have been sold for scrap, at a significant loss for MacGregor.

May argues that MacGregor's loss on the tokens may have been associated with the fact that he ceased trading at the end of 1868. However, research undertaken for Museum Victoria's Trade Tokens Project indicates that MacGregor may have been trading over a significantly longer period than that identified by May. A listing in Ford's 1851 Sydney Directory, for 'M'Gregor, J., grocer, Darling St., Balmain,' could be evidence of an earlier business address, but it is not clear whether this refers to the same man. In 1869 he was listed at 253 George Street, but as his private residence was 253 Elizabeth Street for the entire period between 1863 and 1870, it seems likely that this was a misprint. In 1870, the last year of the period covered by this survey, he was again listed as having a store at 320 George Street, with the Elizabeth Street private residential address.

Samson's National Directory of New South Wales for 1867-1868.
May, T (1988). 'Tokens of George Street,' in Australian Numismatist, 1988 (Special Bicentennial Edition), pp 21-23.
Sydney Directories in the collection of the State Library of Victoria, 1851-1870.

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