The subject of this biography, who rose to become one of the richest merchants in late medieval York, was the son of a local mercer, and as such was admitted to the freedom, along with his brother, John, in about 1385. The two of them were named as executors by John Leversdale, another member of the mercantile community, some four years later, and together they sued a Dartmouth man for a debt of over £42 owed to the deceased. But John did not survive much longer, and the task of administering his estate fell to Thomas during the summer of 1393.
Perhaps because of the scale of his commercial operations, Gare did not really become involved in civic affairs until later life. Although he served a term as bailiff of York while he was still quite young (and was thus responsible for making the return for the parliamentary elections of 1395), over 20 more years apparently elapsed before he agreed to sit on the council of 24, and he had only been an alderman (or member of the 12) for a few months when he first entered the House of Commons. Yet he none the less stood high in the ranks of the ruling elite, as can be seen from his appearance among the earliest members of the influential guild of Corpus Christi, which he, his wife, Katherine, and their two sons helped to found in 1408, and to which their daughter, Alice, was admitted later. Not surprisingly, Gare was a party to several property transactions in York, beginning, in 1401, with his acquisition of three messuages and other holdings in Nether Ousegate, to which he added dwellings and shops in Coney Street, ‘Lytyll Flessamelles’ and Upper Ousegate. He also acted as a mainpernor at the Exchequer for Robert Middleton on his appointment as alnager of Yorkshire, besides attesting the return for York to the Parliament of 1415. It was, however, after his own election as an MP, in 1419, that Gare really began to take an interest in such matters: he sat again in December 1421 (after discharging a term as mayor), and took part in at least five more parliamentary elections.
Gare may well have relinquished some of his responsibilities (although not his aldermanry) in 1427, when he made over most of his holdings in York to his elder son, Thomas, in return for an annual rent of 20 marks. Already mindful of the fate of his immortal soul, he had personally delivered 100 marks to the Austin Friars of York for building work on their new dormitory, in return for which they agreed to perform obits on his behalf. The money was later borrowed back by Thomas, whose widow, Ellen, evidently failed to make good the repayments and was sued in Chancery as a result. Ellen was the only daughter of John Bedford II, a prominent Hull merchant, who may well have done business with Gare on various occasions. The latter survived to see his son’s marriage, as well as his return to Parliament, in 1432, and his election as mayor of York two years later. Indeed, his death (at some point late in 1434 or early in 1435) occurred only a few years before that of Thomas, whose will of December 1438 was proved in the following spring.
