By the second decade of the fifteenth century the Gares were long established among the mercantile elite of York. One Robert del Gare had been made free of the city in 1356 and had served as bailiff in 1364-5, while the later MP’s grandfather, William, had been admitted to the freedom in 1377. By the latter half of the fourteenth century several members of the family were prominent in the wool export trade and at least one of them had lived in Calais and was buried there. Although Robert Gare (probably the son of the Robert who had served as bailiff in 1364-5) appears to have trained in the law and served as recorder of York in 1419, it was in trade that most members of the family made their fortunes into the fifteenth century. The MP’s synonymous father served as bailiff of York in 1394, as an alderman before 1419 and was elected mayor in February 1420, as well as twice sitting in the Commons. By the end of the fourteenth century he had also branched out into the wool trade and at the time of his death in 1434 or 1435 he was one of the richest merchants in York.
Thomas junior was admitted to the freedom of York by patrimony in 1418.
By the second half of the 1420s Thomas senior may have begun to relinquish his commercial interests to his son. On 7 Apr. 1427 he settled his property in Coney Street, Over and Nether Ousegate and the Shambles on Thomas junior in return for an annual rent £20 p.a. during his lifetime.
Following the end of his shrieval year Gare probably joined the council of 24, but by 1 Jan. 1431 he had been elevated to the ranks of the aldermen. In this capacity, and along with his still surviving father, he witnessed that year’s parliamentary election. On 24 Mar. the following year he found himself elected to Parliament alongside another wool merchant, Nicholas Blackburn*.
Gare’s commercial activities aside, scant evidence survives of his private affairs. He was clearly a man of some wealth and in 1436 he was assessed to pay tax on an annual income of £26 from property in the city.
Gare made his will on 1 Dec. 1438. He asked to be buried in his parish church of All Saints, Pavement, and made provision for his funeral there, as well as providing for masses for his soul (some doubtless to be sung by his brother, Master John Gare, who was bequeathed a silver gilt cup decorated with stars for his trouble). A similar bequest of silverware was left to his aunt, the recently-widowed Ellen Ormshead, and to her daughter. set aside 100 marks for the marriage of each of his daughters, to be spent at the discretion of his widow. The property in York that he held in fee simple was to fall to his widow with remainder to his eldest son, Thomas, and his heirs, and if Thomas should die childless, it was to descend to his second son, John, with successive remainders to his daughters, Elizabeth and Anne. The widow was also to enjoy the residue of his goods, on condition that she remained unmarried. Other property in the city was to be disposed of to pay his debts and meet the costs of executing his will. In a codicil added three days later Gare settled a plot of wasteland in Calais on his sons: each was to have an equal share, perhaps in the hope that they would continue the family wool business. In the event of their deaths without issue the land was to pass to Gare’s brother-in-law, Nicholas Bedford. The testator’s son Thomas already held some of his property in Calais and this was now settled on him and his heirs with remainder to Gare’s daughters, sister (Katherine Heseham), and Nicholas Bedford. The date of Gare’s death has not been established with absolute certainty, for while his public career came to a close about the time that he made his will, probate was not granted to his widow until 1 Oct. 1445.
