John Tailyour received 3,757 letters. Most of them concern his business transactions in Jamaica and Scotland. His primary business partners were John and Alex Anderson, Peter Ballantine, David Dick, James Fairlie, George and John McCall, Thomas Renny, and Robert and Simon Taylor. Many of these contacts, including the Andersons, George McCall, and Robert Taylor, stayed in Britain. The Andersons took a particular interest in the slave trade. As a merchant in the American trade, George McCall often sought Tailyour's advice on the markets there, and discussed his own struggles with business after the war. He also served as one of Tailyour's early advisors, as Tailyour began his mercantile career under McCall's tutelage. However, by the 1790s, McCall was asking for Tailyour's advice, as he sought out business positions in Jamaica through John Tailyour's contacts. Eventually McCall's son John became one of Tailyour's clerks in Jamaica.
The correspondence from John McCall, and from David Dick, Tailyour's other clerk, provides some of the most complete information on Tailyour's business and family in Jamaica, after he returned to Scotland. McCall, in particular, often visited Tailyour's Jamaican wife and children, in order to send him reports. Beginning about 1800, the content of McCall's and Dick's letters centered more around their dissolving business partnership. Both men appealed to Tailyour and his cousin Simon for support and arbitration, but the issue of dissolution was settled without them.
Peter Ballantine and James Fairlie were John Tailyour's business partners in Jamaica, and both are an additional source of information on Tailyour's colonial interests after he returned to Britain. Unfortunately, their correspondence begins the year that Tailyour left for Britain (1792), so they offer little information about the founding of their firm, Taylor, Ballantine and Fairlie. However, both Ballantine and Fairlie kept Tailyour advised on the slave, sugar, and dry goods markets, while Tailyour still owned his interest in the Jamaican firm during the 1790s. They, and others, also wrote about events that occurred in the West Indies during the 1780s and 1790s, particularly as they affected the firm's business. They regularly mentioned their concern over the Revolution in St. Domingue in the 1790s, as well as the uprising of the Maroons in 1795, as both events threatened the social stability of Jamaica and its business climate. Ballantine and Fairlie discussed personal information throughout their correspondence, and, once Tailyour sold his interest in the firm, their remarks about family and personal matters became more frequent.
As evidence of the strong ties between personal networks and business, Tailyour's brother Robert and his cousin Simon intermixed both personal and business information in their letters to Tailyour. Between 1788 and 1807, both were continually concerned about the possibility of the abolition of the slave trade. Simon also relayed his business orders to Tailyour, who still carried out work for his cousin during his stay in Jamaica. Robert, with his contacts in the East Indies, provided information on the markets there. His letters contain some of the most detailed information on the issue of Tailyour's mixed race children, including descriptions of the two boys. It was Robert who found schools for the children, as well as professions. A number of letters from the two boys, James and John, are included in the collection. James's correspondence is almost entirely centered on his entrance into the East-India Company army, as well as his initial struggles on the subcontinent after his arrival. John, who worked as a clerk, wrote about his future prospects outside the counting house, and his inability to live on his budget.
Tailyour's mother, Jean, wrote several letters, expressing her concerns about her son's colonial family, and about his future plans for returning to Britain. Tailyour's extended family wrote some of the letters, including the Carnegies (his mother's family), and the Foulertons -- Tailyour's sister Catherine married a Foulerton. Tailyour's connections through the Carnegies and Foulertons, helped him to win a spot in the East India Company army for his son. In return, he helped connect several Carnegies in Jamaica, and gave financial support and advice to the Foulertons.