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.

Sent to Newfoundland via the ship Margaret, the letter instructs Pickering to ship "What fish you have of mine" to Oporto in Portugal, aboard "the best of the Vessels that I am Conserned in . . . ."

A retained copy of a letter sent to accompany a bill of lading for 413 quintals of fish, shipped from Newfoundland aboard the sloop Content, on Samuel Lillie's account.

A retained copy of a letter sent to accompany a bill of lading and invoice for goods shipped from Newfoundland aboard the bark Blessing. Pickering also informs Condy what goods he has been able to sell.

An invoice of goods shipped to Newfoundland per Samuel Lillie, to be consigned to William Pickering.

An invoice of goods shipped from Boston to Newfoundland per Samuel Lillie, to be consigned to William Pickering.

Instructions from Lillie on a number of matters relating to the shipping and selling of fish. Lillie also requests that Pickering "gett me as many men as you can to be under Covenant to proced such voyages in my Vessells as I may send them, on the best terms you can . . . ."

Acknowledges the receipt of four hogsheads of earthenware and other items, on the account of William Pickering.

Lacking ready money, Lillie instructs Pickering to purchase various goods on credit. Lillie promises to repay Pickering, with interest, in three months time.

Lillie requests that Pickering come to Boston, "to discours me about our Affairs." He specifically mentions litigation brought against him by a creditor, Mr. Inglish.

Pickering's retained copy of a letter from Lillie, in which the latter urges the collection of outstanding debts to stave off his creditors: "you have hear with my Letter to Mr Wm Keen to deliver you the Listt of debts by bills bonds & Accotts in his hands which were made by you please to Reiseve all you can for me, and whatt you Reiseve Improve for me for my mostt advantage to this place one hundred and fivety pounds & Consign to Captn Andrew Belcher for my Accott to Remaine with him to Sattisfy what I may be Indebted to you what more you may Reiseve send to London to Mr Robert hackshaw in Good Biils for my Accott . . ."

Another request to collect outstanding debts.

A bond acknowledging that Ponpryes has paid a 55 schilling obligation to Giles Hall. Pickering has signed the document as a witness.

A letter and bill of lading itemizing goods to be shipped to Salem aboard the sloop Dolphin. At this time Belcher was one of the wealthiest merchants in Massachusetts.

A retained copy of a letter from Pickering to Butler. Pickering informs Butler that some of the fishing lines sold by Butler to Pickering are substandard.

Receipt signed by Pickering and Daniel Bray acknowledging that Bray has paid for the future delivery of wine with hard currency and beeswax.

A retained copy of a letter from Pickering to Moody. The previous year, Moody had borrowed "ninety Quintos of merchantable fish" from Pickering. Pickering explains that he would have sought to collect before but had "heard thatt you mett with som troble after you Came home."