Fleeming moved from Scotland to Boston around 1764. In 1765 he worked with William M'Alpine as a publisher/bookseller on Marlborough Street. A few years later, with John Mein he published the Boston Chronicle newspaper (1767–1770), as well as other titles, such as Bickerstaff's Boston Almanack. The partnership with Mein dissolved around 1770. In 1770 Fleeming married Alice Church (daughter of Boston merchant Benjamin Church).
Fleeming sailed from Boston in 1773 on a ship that allegedly carried "a quantity of silver to the amount of 30,000 dollars ... from the Custom House here, being part of the revenue money which has so long been complained of as being unconstitutionally taken from us." In 1778 the Massachusetts General Court prohibited Fleeming (and many other Tories) from returning, being named in the Massachusetts Banishment Act of 1778.
He later travelled to the United States "as an agent for a commercial house. Afterwards he resided in France and died there, since the year 1800."
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- Boston Evening Post, March 11, 176
- Connecticut Journal, August 14, 1770
- Alice Church's father, merchant/auctioneer Benjamin Church, was also the father of medical doctor Benjamin Church (1734-1778).
- Essex Gazette, Dec. 4, 1770
- The Trial of William Wemms, James Hartegan, William M'Cauley, Hugh White, Matthew Killroy, William Warren, John Carrol, and Hugh Montgomery, soldiers in His Majesty's 29th Regiment of Foot, for the murder of Crispus Attucks, Samuel Gray, Samuel Maverick, James Caldwell, and Patrick Carr, on Monday-evening, the 5th of March, 1770, at the Superior Court of Judicature, Court of Assize, and general goal delivery, held at Boston. The 27th day of November, 1770, by adjournment. Before the Hon. Benjamin Lynde, John Cushing, Peter Oliver, and Edmund Trowbridge, Esquires, justices of said court. Published by permission of the court. Boston: Printed by J. Fleeming, and sold at his printing-office, nearly opposite the White-Horse Tavern in Newbury-Street, 1770.
- Boston Evening Post, Jan. 14, 1771
- Boston Evening Post, 26 April 1773
- "Tories prohibited returning." Acts and laws, passed by the Great and General Court or Assembly of the state of the Massachusetts-Bay, in New-England: begun and held at Boston, in the county of Suffolk, on Wednesday the twenty-seventh day of May, anno Domini, 1778. Boston: Printed by Benjamin Edes, printer to the Honorable Council of Massachusetts-State, 1778; p.204.
- Buckingham. Specimens of newspaper literature: with personal memoirs, anecdotes, and reminiscences. 1852