McGregor then began trading from Auckland to Russell, Whangaroa, Manganui and occasionally around North Cape to the west coast ports. Next he invested, in quick succession, in four more ships, the ‘Fairy’, the ‘Ivanhoe’ and the ‘Rob Roy’. At that time Auckland’s population was widely scattered with few suitable roads and travel by sea was the main means of transport and communication. Small river and coastal ships provided the only important links to the city’s surrounding settlements and, being dependent on weather conditions, were not the most reliable form of transport. Attempting to operate a regular service on Northern New Zealand’s exposed coastline was impracticable and by the beginning of the 1870s, McGregor became convinced that the service should convert to steamships as the obvious solution.
Of course steamers required more capital than a small-time trader could command, so he put together a syndicate of businessmen who saw sense and profit in his proposal. The syndicate’s new vessel was the ‘Rowena’ with McGregor holding 26 of the 64 shares and from this small beginning the Northern Steamship Company was born. Under McGregor's command, the ‘Rowena’ traded from Auckland to the northern ports. Over the next eight years, six further steamers were built named 'Argyle', 'Iona', 'Staffa', 'Fingal' and 'Katikati' and trade was extended south to Tauranga and Opotiki on the east coast, and Onehunga south to Raglan, Kawhia and Waitara on the west coast. McGregor gave up work as ships master when closer supervision from the shore was needed.
In 1881 the syndicate was reorganised as the Northern Steamship Company Ltd and took delivery of a new flagship the ‘MacGregor’, a 256-ton steamer. For the first three years under McGregor’s guidance as managing director the Northern Company prospered, commissioning larger steel vessels such as the ‘Clansman’ and the ‘Gairloch’. He certainly gave a significant nod to his Scottish heritage. As the depression of the 1880s hit hard at shipping companies’ freights and incomes, McGregor proposed a reduction in both wages and overtime pay in order to hold down costs. In response the Federated Seaman’s Union, with financial aid from kindred unions, launched its own company, the Jubilee Steamship Company. The Northern Company’s financial situation deteriorated further and McGregor was dismissed for mismanagement by his fellow directors in June 1888.
Nothing daunted, within six weeks at the age of 60 he was back in business with his son, William who was a qualified marine engineer, and some other partners. He purchased the steamer ‘Rose Casey’ but this time his trading was from Auckland to Waiwera and Omaha. His success was immediate and his company flourished over the next 10 years, which demonstrated that accusations of mismanagement levelled at him were unfounded. By the end of the century, he had largely retired from active involvement in the company. He died at his home, Holmdene, in January 1901. He was survived by his two sons and two daughters, his wife Charlotte having died four years earlier. Despite the unpleasant dismissal from the company, he established his contribution to coastal steam communication, which endured till ships gave way to trains and motor vehicles.
His mansion eventually became a boarding house in the 1980s and apparently was popular with transvestites. (DEIRDRE ROELANTS)