It is likely that Smallwood was local to Hythe and it is possible that the Margaret Smallwood who received an exemption from the parliamentary subsidy in the hundred of Heane in 1414 was his mother.
By this stage of his career, Smallwood resided in the town’s Middle ward. Principally a victualler, he commonly sold livestock, herring, salted fish, wheat and, on occasion, woolfells. By the mid 1450s he was charged with maltolts worth up to 30s. a year, indicating that he was then one of the wealthiest merchants in the town.
After beginning his initial term as a jurat in February 1456, Smallwood continued to carry out extraordinary business on behalf of his town. In his first year in the office, for example, he rode to Canterbury and New Romney on an errand arising from the instructions that the warden of the Cinque Ports, the duke of Buckingham, had issued for the defence of the Channel.
In February 1459 Smallwood was chosen as bailiff of Hythe for the first time, and it was as such that he was elected, alongside Thomas Rykedon*, to the Parliament that opened at Coventry in the following November. It was perhaps a measure of the inconvenience of the venue, and the overtly political nature of the Parliament, called to attaint the Yorkist lords, that the Portsmen of Hythe elected two parliamentary novices, albeit from among the town’s wealthiest inhabitants. On his return on 25 Dec., Smallwood claimed daily wages of 2s. 4d. for a total of 41 days’ service, including the ten he had spent travelling to and from the Midlands.
On 2 Feb. 1460 Smallwood relinquished office as bailiff of Hythe and was chosen as a jurat once again. He does not appear to have served in the latter position in the following year, although this unusual omission may be related to a gap in the records. Even if not a jurat in 1461-2, he remained intimately connected with others holding the office. In August 1461, for example, Henry Skinner, referring to him as his ‘brother’, left Smallwood a pigeon house in Hythe in his will, of which he appointed him, Thomas Stace* and John Honywood* executors
In February 1467 Smallwood was again elected as bailiff of Hythe, and in May that year he was returned alongside Thomas Stace to his second Parliament. While Smallwood claimed an allowance of 30 days in connexion with the first session of that assembly, the exact details of their attendances are unknown. Smallwood was certainly in Kent on 21 July 1467, when he attended a meeting of the Brodhull at New Romney, but it is not clear if he attended the sessions held at Reading in November 1467 and May 1468, or indeed the final session held at Westminster in the same May and following June. Neither he nor Stace were present at the Brodhull meeting of July 1467 to report on Parliament’s proceedings. In political terms, Smallwood’s third Parliament was more controversial than his second, since it was summoned in the name of the recently restored Henry VI. He and his fellow baron, William Luns†, departed for Westminster on 23 Nov. 1470, three days before the assembly opened, and returned to Hythe on 22 Dec. On the following 14 Jan. they departed for the second session, with Smallwood returning on 11 Feb. and Luns four days later. Both were allowed the accustomed rate of 2s. a day for their wages, although initially they received only half the sum due to them. They did not travel directly to the second session, since on 16 Jan. they attended a special Brodhull. At this meeting, they and the Ports’ other parliamentary barons received instructions to seek allowance from the warden of the Cinque Ports, Richard Neville, earl of Warwick, for the ships that the Ports had outfitted for the defence of the Channel. Before the dissolution of the Parliament, Smallwood was able to claim £3 in wages as an MP against the payment of his maltolts.
Notwithstanding his Membership of the Readeption Parliament, it is unclear whether Smallwood was among those barons who actively supported the restoration of the Lancastrian King. For instance, while he had contributed money towards the journey north that Warwick and his ally, the duke of Clarence, made in 1469 to join the rebellion of Robin of Redesdale,
A jurat throughout the 1470s and early 1480s, Smallwood served a final term as bailiff of Hythe in 1475-6 and, perhaps, as one of the Ports’ bailiffs at Yarmouth during the fair of 1480. In the same period he continued to make his living as a victualler, although it appears from his maltolts that the sale of fish took up an increasing amount of his business. Often his commercial interests mixed with the affairs of the town, as in 1474-5 when he gave herrings to the Canterbury lawyer, Roger Brent†, and in the following year when he presented a gift of fish to Sir John Fogg. After the hectic activity of 1471, however, his expenditure on the town’s business did not amount to much. He contributed 4s. 5d. towards the benevolence of 1481, a sum he was able to offset against the payments of his maltolts, and in January 1482 he was satisfied of all debts owed to him by the commonalty.
Although last recorded as a jurat of Hythe in February 1484, Smallwood probably remained in office until his death. In his will, dated 25 Aug. 1486 and proved on the following 25 Sept., he sought burial in the chapel of the fraternity of the Blessed Virgin in St. Leonard’s church, of which he had been a member since at least 1480. He provided for ten obits to be said in the chapel, gave 6s. 8d. to its fabric and left each member of the fraternity 12d. Smallwood assigned to his wife, Juliana, £40 in cash and all the ‘store and inventory’ of victuals that had belonged to his mother-in-law, Joan atte Dawne, to enjoy as long as she remained a widow, and ordered a division of his own store of goods between her and his son, Peter. He also left his property in Hythe and Romney Marsh to her with remainder to his son, whom he released from certain debts on the proviso that Peter found a poor priest to sing for his soul for two years. Finally, Smallwood directed his executors, the same Juliana and Peter, to dispose of the remainder of his goods and chattels for the benefit of his soul.
