Richard Jeffery Cleveland was born on December 19, 1773 in Salem, Massachusetts, United States. He was the eldest child of Stephen and Margaret (Jeffry) Cleveland. His father, when sixteen years old, had been kidnapped on the streets of Boston and impressed into the British navy; later he helped to design and equip Revolutionary privateers and held one of the first naval commissions issued by the Continental government.
Richard received the limited education. He left the school at fourteen years old.
About 1784 Cleveland entered the counting-house of Elias Flasket Derby, and at eighteen went to sea as captain’s clerk. A year later he completed a voyage as second mate, the first mate, Charles Derby, being nineteen, and the captain, Nathaniel Silsbee, not yet twenty. He himself was a full-fledged captain at twenty-four. In 1797, finding himself footloose in Havre with $2, 000 in his pocket, and eager to provide for the comfort of his aging father, he embarked on the series of daring voyages and trading ventures to which he owes his fame.
When he returned to Salem, May 13, 1804, he brought with him a fortune of $70, 000. In the interim he had sailed twice around the globe, had engaged in a number of successful commercial transactions, had matched wits with Indians on the Alaskan coast and with British, French, and Spanish officials and naval men on the high seas and in a halfdozen far-flung ports, had had a close escape from Malay pirates, had quelled a mutiny on the China coast, and—most brilliant of all—had performed three extraordinary feats of navigation in small sailing vessels.
With a crew of four miscellaneous incompetents and an inexperienced Nantucket boy as mate, he had taken a cutter-sloop of forty-three tons from Havre to the Cape of Good Hope (December 1797 - March 21, 1798). In a vessel only slightly larger, with a short-handed, disaffected crew, he beat his way, in midwinter, in the monsoon season, from Canton to Norfolk Sound on the Alaskan coast (January 10 - March 30, 1799). Finally, in a boat of only twenty-five tons, he sailed from Balasore Roads, near Calcutta, to the Isle of France (now Mauritius) in forty-five days (March 29 - May 14, 1800). It was at Mauritius that he met his life-long friend and partner, William Shaler.
In 1804 he bought a beautiful estate in Lancaster and looked forward to a serene domestic life amid his books and flowers; but in 1806 he was compelled to go to sea again, the enterprises in which his winnings were invested having come to grief, and at sea he remained, except for short intermissions, until the end of 1821. During these years he made and lost several fortunes. Twice his ship and cargo were confiscated: in the Caribbean by the notorious Admiral Cochrane of the British navy, at Naples by Napoleon. Throughout these years he acted with his old foresight and competence, but his luck was almost uninterruptedly bad.
When his friend Shaler was made consul at Flavana in 1828, Cleveland went with him as vice-consul and shared equally in the perquisites of the office. Shaler died there of cholera in 1833; Cleveland was ousted from his post by President Jackson, and found a berth for a while in the Boston Customs House. From 1845 till his death he made his home with his son, Horace W. S. Cleveland, first at Burlington, New Jersey, and after 1854 at Danvers, Massachusetts, where he died.
Cleveland was no mere trader and adventurer. He was one of the greatest of the great race of New England sea captains—intrepid, skillful, clean, temperate, honest—but regard for Spanish trade regulations and for the nice conduct of neutrals in wartime was no part of his code. He also authored an important book that chronicled international trading ventures.
Cleveland married his cousin, Dorcas Cleveland Hiller on October 12, 1804.
