The collection consists of sixteen documents—eleven letters and five business records—retained by Pickering in the course of his commercial career. Nine of these items pertain specifically to Pickering's dealings with Samuel Lillie. The earlier of these (1703-1706) relate to the Newfoundland trade (Pickering appears to have served as a kind of agent for Lillie's interests there); the later items (1706/7-1708) relate to Lillie's debts. There are a total of six letters written by Lilly to Pickering. The Pickering letters in the collection are retained copies, in his hand.