By 1278 the Prides had acquired extensive property in Shrewsbury, including numerous tenements and more than 200 acres of land, and had taken up residence in a mansion on the north-west side of what is now known as Pride Hill. They numbered among them several 14th-century bailiffs and MPs, notably Roger Pride, who represented Shrewsbury in Parliament 19 times between 1312 and 1340. Thomas’s father, the bailiff of 1346-7 and MP of 1338 and 1339, died before 1375 when he and his widowed mother entered into recognizances for 288 marks under the Shrewsbury statute merchant with John Shotton; and in the following year, in connexion with these bonds, they settled annual rents of £5 on Richard Grafton.
Thomas may have been a lawyer. From 1376 he was continually active in municipal government for more than 40 years. During this period he was selected six times as an assessor, three as a coroner, and four as a bailiff, and sat for Shrewsbury in no fewer than 11 Parliaments (in six of these, in 1393, 1394, 1402, 1407, 1411 and 1414 (Apr.), while occupying an official post). During his second bailiffship (in association with William Biriton), in November 1380 and as a result of petitions to the Parliament of Northampton then sitting, a royal commission was set up to inquire into a complaint by certain of the townspeople of Shrewsbury that, whereas normally the bailiffs were elected by the ‘more sufficient men’ of the town from among themselves, certain individuals of inferior status, being prompted by the ‘evil counsel’ of rabble rousers, including Pride and Biriton, had chosen these two as bailiffs before the appointed day (1 Sept.), squandered money from the common fund and risen against their betters. Despite the allegations, on 26 Mar. Pride was himself named on a second commission to settle these local differences and disorders and to arrange for a fresh election to be held. In fact, this commission never took effect, for three days later, at the earl of Arundel’s Shropshire castle called ‘Isabel’, and following a fortnight’s negotiation, 12 ‘more sufficient’ men of Shrewsbury were elected to assist in the government of the borough until September 1383. Pride was one of their number, and he may even have continued to hold the bailiffship for the rest of the term. Five years after this, in August 1389, when bailiff once again, he witnessed at Shrewsbury abbey a further ‘composition’ to reform the administration of the town. Perhaps it was on this occasion that he came to the favourable attention of the abbot, who was to appoint him as his proxy in the forthcoming Parliament of January 1390, and again in 1393. On 19 Jan. 1394 the borough forwarded to Pride and his fellow MP, Hugh Wigan, £4 to cover their expenses at the Parliament due to assemble the following week, and in June reimbursed him for further costs of £1 incurred while attending the Commons at this time. In addition, for travelling to London that summer to obtain a writ at the King’s bench on the commonalty’s behalf, Pride received £2 13s.4d. However, it was not long before he was again caught up in local disputes: between September 1398 and May 1399 the then bailiffs, William Biriton and Robert Thornes, alleged that he had embezzled money allowed by the Council as rebate to the borough on its fee farm and contributions to parliamentary subsidies over the previous four years. It may have been on this account that orders had gone out for his arrest in October 1396, May 1397 and May 1398, and that he, to protect himself, had taken out in June 1398 a royal pardon, in which he was described as of Shrewsbury alias of Ruthin.
In May 1389 Pride had obtained a royal licence to found two chantries in St. Alkmund’s church, Shrewsbury, dedicated to the Holy Cross and St. Mary, and to provide for prayers for Richard II, Queen Anne, and himself. After making settlements on the church of eight messuages (situated in Barker Street, Mardon, Castle Street and Fish Street, in the suburb of Coleham and at Bicton),