The Hakluyt family was of Welsh descent, having originated in Radnorshire, but by the time of Leonard’s birth in about 1352 it had long been established in Herefordshire. His own landed property is difficult to trace in its entirety. In Herefordshire he is known to have held an estate at Stoke Edith, just east of Hereford, and he may also have owned the manor of Lower Venn, north of the city, as well as premises at Longford, near Leominster. At his death he possessed (unspecified) lands in Worcestershire. Outside the marches he had estates in Somerset and Dorset worth £66 13s.4d. p.a. (in 1412), including the manor of Oldland and property in Shepton Mallet and Broadmayne. His marriage brought him further holdings in the south-west, namely the manor of Grove in South Brent, Somerset, and properties at Degembris, Tremough and Carvath, in Cornwall.
Hakluyt’s career began in the service of the Mortimers, to whom he appears to have been a highly valued servant. In February 1380 he received royal letters of protection as about to accompany Edmund, earl of March, to Ireland, where the latter had been appointed King’s lieutenant. Evidently, he took an active part in Edmund’s Irish campaigns, for in September 1381 the earl granted him, as his esquire, an annuity of £10 for life from the manors of Erith and Swanscombe, Kent. Edmund died at Cork three months later, but Hakluyt (as nothing is known of his activities in England at this time) may have remained in Ireland in the service of Sir Thomas Mortimer, deputy of Roger, the young heir to the earldom.
On the accession of Henry IV, Hakluyt’s patrons the Mortimers (as the declared heirs of Richard II) became a focus of opposition to the new dynasty. How far this affected his career is unknown, but there is no record of any official employment given him between 1399 and July 1401, when he was among those summoned to a great council which was to be held at Westminster in the following month. By this time the Welsh were in revolt under Owen Glendower, and Sir Leonard, as sheriff of Herefordshire during most of 1402, must have been much involved in the campaigns against them. Moreover, when, in November 1402, Sir Edmund Mortimer, uncle of the young earl of March, went over to Glendower, Hakluyt remained loyal to the Crown and in October 1403 he was one of those empowered to receive into the King’s peace the Welsh rebels of Radnorshire, Breconshire and Monmouthshire. Nevertheless, he continued his connexion with the main line of the Mortimers, and in the following month he gave up one of his annuities for the support of the late Earl Roger’s daughters. He may well have been acting as a Mortimer receiver at this time, for in April 1404 he was ordered to hand over to the Crown such forfeited rents of the traitor Sir Edmund as were then in his keeping. On 30 Oct. following, while attending the Parliament at Coventry, he was granted a royal lease of the Mortimer manors of Marden and Much Marcle. Six months later he was commissioned to take the musters of the royal garrisons of certain castles in southern and central Wales.
Hakluyt’s fourth return to Parliament, in 1404, had been for Somerset, and it was there that he apparently spent much of his later life, probably at the manor of Grove in South Brent, where both he and his wife were to draw up their wills. Between 1405 and his death he sat on royal commissions relating to the south-western counties but (possibly because of a continuing link with the Mortimers) he also remained influential in Herefordshire, where he was again made sheriff in November 1408. This term of office was, however, cut short in February following, when he was for some reason thought to have died and his executors were ordered to hand over all relevant accounts to a successor. In point of fact he was to live on for several more years. In 1410 he was a beneficiary of the will of (Sir) Thomas Clanvowe (his fellow MP for Herefordshire in 1394), who left him a gilt cup ‘for gret truste that y have in his socoureyng and helpe of my wife at here nede’. He made his own will on 3 Aug. 1413, and was dead within a week.
Sir Leonard’s testament is a long and interesting document, reflecting his position as a notable figure both in the Welsh march and the south-west. He requested burial at the Franciscan church at Bridgwater, to which he left £20. Further legacies went to the parish churches of South and East Brent, Somerset, and Lugwardine and Much Marcle, Herefordshire, as well as to the friars at Hereford, Ludlow, Bristol and Bridgwater and the Carthusians at Witham and Henton. Five pounds each was donated to the confraternities of the Holy Trinity at York and of the Palmers at Ludlow (provided they would admit his widow). Similar sums were to be devoted to the repair of roads in Brent and to the construction of a causeway near Longford. In all, Sir Leonard’s monetary bequests (including gifts to servants and friends) totalled more than £250. His executors included his widow, Margaret, and Richard Pecock, rector of Shepton Mallet. The former, having retired to the Franciscan house at Bridgwater, survived her husband by only a year, dying between 29 July and 11 Aug. 1414.