Landowner
Thomas Giffard, despite his own longevity, was to outlive his father by only four years, so it was particularly fortunate for him to acquire property young. In his first wife's right, he was lord of Cubley itself and also Caverswall, a small manor to the north-east of Stafford, on the edge of the Staffordshire moorlands. The couple settled at Caverswall Castle, and this was to remain Giffard's main home, even after his wife's death, which was by 1529, as this was the year of his second marriage.
However, Giffard did not content himself with waiting to inherit the family estates. He was Escheator for Staffordshire in 1523–24. Thereafter he sought positions managing the estates of other major landowners. He became bailiff and custodian of Brewood Park, a major part of the Bishop of Coventry and Lichfield's land in Brewood parish. For this he was receiving £5 0s. 8d. in 1535. The sum was not huge but for ambitious landed gentry such posts were a foot in the door: later, the Giffards would become not merely keepers but tenants of the park and able to profit more amply from managing it. Giffard also took on a similar post at the manor of Shenstone, Staffordshire.
The passing of the Dissolution of the Lesser Monasteries Act in 1536 brought further opportunities, opening up a wide range of small properties for landowners and entrepreneurs at Giffard's level. Soon he was bidding for Black Ladies Priory, a dissolved nunnery to the west of Brewood. Sir Edward Littleton, his contemporary and neighbour at Pillaton Hall was a competitor, with Bishop Rowland Lee on his side. The matter was referred to Thomas Cromwell, who decided in favour of Thomas Giffard, described as "of Stretton", a manor on the southern edge of Penkridge and close to Black Ladies, which he had taken on by this time. Giffard paid £134 1s. 8d. for the property, which consisted of the site and grounds of the priory building itself, including the church and churchyard a water-mill, together with a tract of grazing land in Brewood – all valued at £7 9s. 1d. a year. He built a new house on the site and seems to have moved to live in it. After his father's death, he leased Black Ladies to Humphrey, a younger son, although the reversion remained with John Giffard, his heir.
Sir Thomas Giffard was sufficiently prominent, even before inheriting the family estates, to be pricked High Sheriff of Staffordshire three times: 1529–30, 1547–8, and 1553–4. He was a Justice of the Peace for Staffordshire from 1532 until his death. He inherited the Giffard estates only in 1556. As son and heir, he obtained the lordships of Chillington, Marston, Plardiwick near Gnosall and Walton in Eccleshall, and as a lessee of the Crown the lordship of Pattingham. Together with his own substantial estates, all this made him, for a short time, a very wealthy man.