Series II. Business Papers, 1786-1823, include correspondence, accounts, receipts, and shipping papers for his store, shipping ventures, and medical practice. The bulk of the business and miscellaneous correspondence contains letters regarding settlement of accounts and debts. Additional letters include correspondence on the purchase or sale of goods from Drury's store, the purchase of lottery tickets from a church in Bristol, Rhode Island, and correspondence concerning land owned by Drury in Rhode Island. The miscellaneous business accounts and receipts include purchase orders, accounts, and receipts for the store owned by Drury.

The Thomas Drury correspondence contains letters to and from John and Thomas, both while Thomas managed a store in Providence, Rhode Island for John, and later during Thomas' sea voyages. These letters discuss the activities of the stores, both in Providence and Marblehead, and after 1798 of Thomas' maritime ventures while attempting to sell surplus medical supplies.

The shipping papers reflect John's efforts to export surplus medicine through Thomas and other captains. These records contain correspondence, accounts of sales, and insurance policies for shipments to Lisbon, the West Indies, and southern United States. Included here are also the papers for the schooner Mary, owned by John and mastered by his brother Thomas, which was condemned.

Only a single folder of medical records documents John's career as a doctor. The bulk of these records contains accounts and bills to patients. There are also a few letters that discuss ailments, a letter relating to his selection as vice president of the Essex Southern District Medical Society and a few notes on ailments.