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The collection focuses primarily on John Tailyour, a Scottish merchant who traveled to North America and Jamaica in the 1770s and 1780s to conduct business, before finally returning to his home in Scotland in 1792. His correspondence is heavily business related, centering especially on his trading of slaves, foodstuffs, and sundry goods. It also chronicles the current events in both Jamaica and the Empire. Many of Tailyour's correspondents debate the meaning and merit of the cessation of the slave trade in the late 18th century, as well as the military events of the American and Haitian revolutions, and of the Maroon rebellion of 1795. The papers also include letters between John and his family in Scotland regarding John's mixed-race Jamaican children. He sent three of his children to Britain to be educated, which caused much family concern. Tailyour's account books and financial papers relate both to his Jamaican estate and business, and to his Scottish estate, from which he received added income from rents. The accounts for this estate continue for several decades after Tailyour’s death in 1815. A number of disparate and miscellaneous letters, war records, photographs, and realia that belonged to various members of the extended Tailyour family date mainly from the late-nineteenth and early-twentieth centuries.

The collection has three substantial parts. The most comprehensive and cohesive section is the one concerning John Tailyour, until his death in 1815. The second part contains business papers and accounts related to the Tailyour estate. The third part is the least integrated, and consists of a variety of family papers, photographs, military memorabilia, and other miscellanea.

The Tailyour papers date from 1743 to 2003, with the majority of the collection concentrating in the period from 1780 to 1840. Within these bulk dates, are the two largest portions of the collection: the correspondence and accounts of John Tailyour until his death in 1815, and the account records of the Tailyour estate after 1815.

Seven boxes contain John Tailyour's personal and business correspondence of 3757 letters. The letters focus on Tailyour's mercantile activities in the Atlantic market, especially on the slave trade, its profitability, and the threat posed by abolitionists. Tailyour's correspondence also chronicles personal and family matters, including the education and provision for his mixed-race children from Jamaica. In addition, the collection contains four of Tailyour's letter books of 1116 copies of retained letters that cover the period from 1780 to 1810, with the exception of the years 1786-7 and 1793-1803. In these letters, Tailyour's focus is business, particularly as it relates to the slave trade, but he also includes personal messages to his friends and family.

Tailyour's business papers contain 32 loose account records, as well as five account books documenting the years between 1789-90 and 1798-1816. These primarily concern his Kingston and Scottish estates, including the expense accounts and balance sheets for each, as well as the finances of his merchant activities during the period. Finally, 38 documents of probate records for John Tailyour mainly relate to his landed estate.

The latter portion of collection within these bulk years (1815-1840) also contains correspondence and accounts, although the 228 letters are almost entirely concerned with business accounts. These focus on Tailyour's estate after his death, with John's brother Robert as the main correspondent. Additional materials include 1761 business papers that chronicle the finances of the estate, 11 account books, and 6 hunting books. The business letters and account books detail the estate's expense accounts and receipts, as well as the balances for their annual crops, salmon fishing business, and profits derived from the rents collected on their land. The hunting books contain descriptive accounts of the family's hunts and inventories of their hunting dogs.

The third, and final, part of the collection consists of Tailyour family records (bulk post-1815), including 49 letters from various family members in the late-nineteenth and early-twentieth centuries and five letterbooks, kept by Alexander Renny Tailyour and Thomas Renny Tailyour. 4 account books are also present kept by Alexander Renny Tailyour and others. Some of the records concern the First World War, including a group of prisoner-of-war records sent from Germany, and journals kept at home that detail news of the war, and daily domestic activities.

The family history documents include 64 genealogical records and 58 probate records. Many of the genealogical items are brief notes on family history, and sketches of the family tree, including a large family tree that spans several hundred years to the present day. The probate records contain one will from the late-nineteenth century, but are otherwise entirely concerned with John Tailyour's estate in the years immediately after his death.

Of the printed records, Memoirs of my Ancestors (1884), by Hardy McCall is a genealogy of the McCall family, and Tailyour's Marykirk and Kirktonhill's estates are described in two printed booklets, one of which is an advertisement for Kirktonhill's sale in the early-twentieth century. Other printed material includes 14 various newspaper clippings concerning the family over the years, and 12 miscellaneous items.

The illustrations, artwork, and poetry comprise 14 fashion engravings, 12 sailing illustrations, a picture of a hunting cabin, two silhouettes, and a royal sketch, all of which date from the early- to mid-nineteenth century. Kenneth R. H. Tailyour's sketches are represented in two sketch books created in his younger years (1917 and 1920). Loose records of poetry, as well as a book of poems from George Taylor, are in this section.

The 221 photographs are of the Tailyour family from the late-nineteenth to the twentieth century, with the majority falling in the early decades of the twentieth century. Most are portraits of the Tailyour family from the early twentieth century, particularly Kenneth R. H. Tailyour.

The 138 pieces of ephemera are, for the most part, postcards of foxhunts during the nineteenth century. These announce the almost-weekly family foxhunts during the middle years of the nineteenth century. The 19 items of realia, include Robert Taylor's quill pen from 1826.

The audio-visual portion of the collection contains three items: a compact disc with an audio interview of John Dann, Director of the Clements Library, on National Public Radio's "The Todd Mundt Show;" a compact disc with photos of the West Indies; and a collection of photographs of the Tailyour papers in their uncatalogued state, and of the festivities surrounding the acquisition of the collection.

Finally, miscellaneous material of 18 pieces includes Robert Taylor's commonplace book of short stories, letters, and poems; the catalogue of Robert Taylor's books; James Tailyour's 1771 style and form book; and a communion book.

Thomas O. LeRoy's journal contains log entries, diary entries, and drawings that he composed while sailing onboard the merchant ship Natchez from New York to Valparaíso, Chile, and back to New York between September 1841 and May 1842. LeRoy recorded the ship's progress, his observations about seafaring life, the scenery he passed, his travels in Chile, and other topics.

Thomas O. LeRoy's journal contains approximately 85 pages of log and diary entries that he composed while sailing onboard the merchant ship Natchez from New York to Valparaíso, Chile, and back to New York between September 1841 and May 1842. Also included are 9 drawings he made on the voyage, an inventory of the belongings he carried during the trip, and 7 pages of double-entry bookkeeping accounts of Captain Robert Waterman of the brig Konohassett and of Theodore Lewis of the brig Philip Howe.

LeRoy began his journal with a brief entry on August 28, 1841, and the Natchez set sail under Captain Robert Waterman on September 1. Between September 1 and November 11, LeRoy regularly kept detailed log entries documenting the ship's course, winds, and notable onboard occurrences. The log entries were often interspersed with prose accounts of life on the Natchez, in which he mentioned seeing birds and aquatic animals, and described the scenery, particularly after the Natchez reached the Brazilian coast. In early November, LeRoy interrupted his log with detailed descriptions of the scenery around Tierra del Fuego, and he resumed his regular entries until reaching Valparaíso, Chile, on November 15.

LeRoy recorded his impressions of the Chilean people and discussed his travels around the country, which included visits to nearby towns and to Santiago. He noted other ships in the harbor, reconsidered his decision to embark on a seafaring life, and discussed sailors' religious beliefs. The Natchez began its return journey on February 6, 1842, and LeRoy continued to write journal entries about his experiences onboard, sometimes mentioning his eagerness to return to his family. After a brief stop at Pernambuco, Brazil, the ship sailed through the Caribbean and, at a point of about 160 miles from New York, LeRoy composed his final entry, dated May 1, 1842. The journal is followed by an inventory of the belongings LeRoy brought along on his trip. He dedicated the volume to Midshipman Charles Cooper of New York.

LeRoy drew 9 pencil sketches during his time on the Natchez.

• Cape Horn
• Juan Fernandez, "the Island where Robinson Crusoe resided"
• Huasco, Chile
• "Attack on fort Moultrie by the British"
• "Ship Natchez... in a snow squall"
• "View of the Brazil Coast near El Salvador with Negro Fishermans Hut on a small rocky Island"
• Cape St. Augustine, Brazil, and Saint Aleixo Island
• Brazilian coast near Pernambuco, with a view of a "Coca Nut Plantation"
• View of Brazil near Cape São Roque

The volume holds 7 pages of double-entry bookkeeping accounts. These record the finances of Theodore Lewis of the brig Philip Howe and those of Robert Waterman during a trip to Asia onboard the Konohassett.