The Shirley family had held the manor of Lower Ettington in the male line since the Conquest, but derived its name from another of its manors, acquired subsequently in the 12th century. To these holdings the Shirleys added ‘Houne’ and other properties also in Derbyshire, and Barnham, far away in Suffolk. Sir Thomas Shirley, reputed to have fought at Crécy and Poitiers and noted for his benefactions to the college in the Newarke, Leicester, where he was buried ‘in a large and stately monument’, left his son and heir, Hugh, still an infant at his death, which occurred shortly before April 1362. Hugh’s mother, either an illegitimate daughter of Ralph, Lord Basset (d.1343), or more likely that lord’s stepdaughter, then made a widow for the fourth time, took as her fifth and sixth husbands Sir John Woodhill (d.1367) and Sir Gerard Braybrooke I (d.1403). It was to Braybrooke that in 1372 John of Gaunt, duke of Lancaster, sold the wardship of the Shirley estates for a single payment of 100 marks. Hugh would appear to have come of age shortly before March 1383, when he confirmed his mother in her life tenancy of the lands of his inheritance, his own full possession being thus deferred for about ten years. The Shirley estates were to provide him with an annual income of at least £40 a year.
Throughout his career Shirley served the house of Lancaster, linked by the ties of lordship forged in his youth while under the guardianship of John of Gaunt. Having been contracted on 14 Mar. 1386 as the duke’s esquire to serve in his army overseas, he probably stayed with Lancaster, engaged in his wars in Spain and France, until the duke returned to England late in 1389. Duke John’s high regard for him was expressed in the award of two annuities for life: the first of £20 charged on the issues of the honour of Leicester; the other, which he shared with his wife, Beatrice, of as much as 100 marks derived from the honour of Tutbury. In the 1390s Shirley was among the duke’s chamber knights, while his wife also had a place in the household, as one of the Duchess Constance’s closest companions. Furthermore, he also enjoyed the esteem of Gaunt’s son and heir, Henry of Bolingbroke, who in 1391-2 gave him a present of some jewellery. Shirley established strong ties with other leading Lancastrian retainers, such as Sir Walter Blount, for whom he provided securities at the Exchequer in 1392, Sir John Bussy and Sir John Dabrichecourt. These three all came forward on his behalf in August 1394 to offer guarantees under pain of £200 that he would keep the peace in future towards Sir Thomas Erdington. His dispute with Erdington concerned property at Barrow-upon-Soar from which Sir Thomas had long sought to oust Lord Basset; Shirley had kept up the feud with a midnight raid on Erdington’s own manor-house there at the head of a band of 200 armed men. In the spring of 1397 Sir Hugh was in London making preparations for a voyage to Bayonne, probably on Lancaster’s business, and in the will John of Gaunt made on 3 Feb. 1398 he was left a bequest of 100 marks. Richard II evidently considered it worthwhile to procure Shirley’s compliance following the seizure of the ducal estates by the Crown a year later: on the point of departure for Ireland on 24 May 1399 he issued orders to the duchy officials for the continued payment of his annuities.
It was at this stage in Shirley’s career that his title to the Basset estates received a serious challenge from Edmund, earl of Stafford, Lord Basset’s coheir in right of blood, who having succeeded to a number of Lord Ralph’s manors under the terms of entails made in the early 14th century, nevertheless considered Shirley to have usurped his interest in the rest; and Sir Hugh’s failure to change his name to Basset as required by his late uncle no doubt gave him a pretext. However, in an agreement apparently made on 20 July 1403, Earl Edmund formally ‘granted’ Shirley the estates Lord Basset had willed to him, with reversion in default of male issue to the Staffords, which concord the earl was bound to honour under pain of £12,000. The indenture was never sealed, for on the following day both men were slain at the battle of Shrewsbury. A tradition, well established by Shakespeare’s day, has it that they were two of the three knights (the other being Shirley’s colleague, Blount) who, clad in royal armour in order to impersonate the King, successively encountered and fell in single combat under the victorious arm of the earl of Douglas, their deaths being avenged by a fourth champion, Prince Henry.
Shirley left a widow, Beatrice, a son, Ralph (still a minor) and five unmarried daughters. Henry IV showed concern for their welfare: on 10 Sept. following he granted Beatrice custody of the Shirley estates to the value of £44 10s. a year, and on Oct. he gave her Ralph’s wardship and marriage. Furthermore, when When shown the unsealed agreement made between Sir Hugh and the earl of Stafford, he commanded that the accord be kept as if formally ratified by law. From 1406 Beatrice possessed a lease of four of the Basset manors (as granted her by Lord Ralph’s feoffees) to hold until her son attained his majority; and following that event she formally conveyed to him the family estates in return for a regular pension.