Thus the poet James Hogg, the Ettrick Shepherd, complained to publisher William Blackwood about a dispute into which he had drawn Hogg's banker, George Craig. The affair, over what Craig referred to with exasperation as the ‘mighty matter’ of a £50 debt owed to Hogg, led to handwringing on all sides. At this juncture Craig was highly experienced in banking after succeeding his father as agent for the Leith Bank. Hogg described him perceptively as ‘a most honourable and disinterested man’, although ‘noted for a sort of stubborn perverseness when in the least crossed’.

The years after the Napoleonic Wars saw declining prices for agricultural produce and there was an economic depression from 1819–1822. As a result, bank failures in the 1820s were common. The Leith Banking Company was not one of Scotland's major banks and it faced growing competition, particularly as larger competitors, such as the Bank of Scotland and the British Linen Company Bank, developed their branch networks. The financial crash of 1825, which so badly affected Sir Walter Scott (whose main bankers were Sir William Forbes and Company and the Bank of Scotland), largely resulted from speculative investment but it also had implications for Craig and his clients.

Many of Craig's letters relate to banking: in fact, there are more letters to bankers than any other category of correspondent. For the first six months of 1827, for example, 21.7 per cent of all his correspondence was addressed to bankers. Nearly two-thirds of these letters went to the Leith Bank, but that should not disguise the variety of bankers across the country with whom he corresponded. Many of these letters are short, cast in the efficient, laconic language of banking professionals speaking of bills of exchange received, remittances sent, and protests for non-payment made. Craig's office spent much time chasing debtors, employing diligence (legal procedures to elicit the payment of debts) and attempting to avoid the need for formal enforcement by cajoling payment through encouragement or threats.