Fleming’s career is one of the least well documented of those of the men who represented London in Parliament in this period. Little is recorded of his origins, although it is probable, given his connexions with Kent, that he was related in some way to John Fleming† of Rochester. The lack of information about his career is not helped by the paucity of evidence surviving for his company, the Ironmongers. It is, nevertheless, clear that he was one of the most prominent and wealthy members of his craft: he was named as master of the company in March 1463 when the Ironmongers acquired their first charter from Edward IV. As was frequently the case with the London companies, this was not a ‘foundation’ charter, as the Ironmongers had undoubtedly formed their guild some years before. Thus Stow’s description of Fleming as the first master of the Company reflected the importance that such charters often came to assume, particularly when other records did not survive.
Fleming’s activities in the property market are similarly difficult to reconstruct. It is clear that he lived in the riverside parish of St. Magnus the Martyr where, in December 1453, he was said to be a churchwarden. The same year property in Thames Street was quitclaimed to Fleming, Beaufitz and a fellow ironmonger, Nicholas Marchall, by Richard Cokflete of Rochester and Joan his wife. While Joan was the daughter of a London fishmonger, Richard Toky, and sole heiress of her brother Roger, the transaction provides evidence of Fleming’s enduring connexions with the city of Rochester.
Fleming’s civic career followed a conventional path, beginning with service on committees appointed by the city government in the mid 1450s. In April 1458 he made his first bid for membership of the aldermannic bench, although in the contest for the vacant ward of Vintry he was beaten by Thomas Oulgreve by six votes to four.
In March the next year Fleming twice put himself forward as a candidate for the aldermanry. He failed to be chosen for Dowgate on the fifth of the month, but three days later was selected for the ward of Farringdon Without. In September the same year he was chosen as sheriff, and two months later he managed to transfer his aldermanry to Billingsgate Ward, which was adjacent to his own parish of St. Magnus.
