Series III. Second Generation Business and Personal Papers contains the records of Richard's sons, Elias Hasket (1739-1799) and John (1741-1812) Derby. Subseries A. Elias Hasket Derby Papers includes business correspondence, financial papers, account books, legal documents, and estate papers from 1761 to 1827. Purchase and sale of commodities, petitions for employment, settling of accounts, and transactions of business are included in Elias Hasket's business correspondence, which covers the years 1775 until 1798 (box 16, folders 5 and 6). The lengthy correspondence between Elias Hasket and Metcalf Bowler, from 1781 until 1786, concerns the purchase and payment of coal for the French army. A separate folder (box 16, folder 7) contains the correspondence, receipts, and deeds for land owned by Elias Hasket in Raymondtown, a township in the County of Cumberland, Maine. The bulk of Elias Hasket's papers comprise the miscellaneous receipts from 1761 to 1799, and accounts from 1762 until 1799. All of Elias Hasket's account books contain both shipping and non-shipping entries. The consecutive account book volumes, Ledgers B and C (Volumes 9 and 10), list name and occupation for account entries. A separate index is enclosed in the front of Volume 10.

The legal papers (box 18, folder 9) of Elias Hasket Derby include property deeds, promissory notes, agreements, a liquor license, stock certificates, and an inventory of goods and property deed for a farm in Wolfborough, New Hampshire. Of interest here is a list of furniture received by Elizabeth Crowninshield upon her marriage to Elias, and a bond between Richard Derby (1712-1783) and Elias Hasket for a gift to Elias Hasket's son, Richard Crowninshield Derby. There are also estate papers from 1763 until 1774, and a partial will for Elias Hasket's mother-in-law, Anstiss Crowninshield. The estate papers of Elias Hasket Derby (box 19, folders 1-2) include all documents that do not pertain to the shipping business. Of special note is the inventory of Elias Hasket's house and goods purchased from the estate, and the executor's accounts of the settlement of the estate. Two estate account books record the transactions of the estate following Elias Hasket's death.

Subseries B. John Derby (1741-1812) Papers contains correspondence to John (1741-1812) and Elizabeth Derby from 1786 until 1801 (box 19, folder 3). The majority of the letters are from either Sally (Gardner) Crowninshield or Martha (Derby) Prince. The letters relate the activities of their respective families.