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Sir Richard, the son of Sir Kynard De la Bere of Kinnersley Castle and Joan De la Barré of Clehonger, was a very wealthy man. At his father’s death, he had inherited the estates of both his grandfathers and, splitting life between the two manors, he lived the life of luxury. He became Sheriff of Herefordshire and his pre-eminence in the county can be easily judged by examining his fine brass in Hereford Cathedral. Here are displayed Richard, his first wife Anne daughter of John Tuchet, Lord Audley, his second wife Elizabeth daughter of William Mores (Sergeant to the Hall of Henry VII), one son and four daughters by Anne, and ten sons and six daughters by Elizabeth. He apparently took an interest in political affairs during the “Wars of the Roses”, though whether he took up arms is unclear. Sir Richard did have Beaufort/Lancastrian connections, but he appears to have been a Yorkist with personal connections to Henry Stafford, Duke of Buckingham through the same source. Sir Richard’s brother-in-law, James, Lord Audley, was married to Margaret Dayrell, half-sister to Buckingham. Their mother was co-heiress of Edmund Beaufort, Duke of Buckingham.  

After initially conspiring to place Richard, Duke of Gloucester on the throne at the death of Edward IV, the Duke of Buckingham later switched allegiances. He had, no doubt, received many broken promises and his position had not become as elevated as he had hoped. The struggle for power, which might have been over had Richard III's reign not proved so unpopular, was awakened once more, and it is possible that, as a cousin to the King, Buckingham was pushing for the throne himself. However, he meanwhile hooked onto a better bet and raised his standard, for the claimant Henry Tudor, in the Welsh Marches where he owned the castles of Hay and Huntingdon, and where his influence held sway. The revolt failed due to the impassable Severn and treacherous comrades, and the Duke was forced to flee from Brecon to Weobley. Here he stayed but a week, calling a meeting of all his local supporters, before departing again. His son (and heir), however, was left behind in Herefordshire, hidden with Sir Richard De la Bere and his wife, Elizabeth, at Kinnersley Castle. The Duke of Buckingham was to send Sir Richard a token when his son was to join him, but he was caught and hung in Salisbury before he ever had the chance. The young lad survived however, despite having a price on his head and the castle being searched several times. He eventually escaped to Hereford.

In the more stable reign of Henry VII, when Henry Tudor had finally succeeded in taking the crown, Sir Richard became embroiled in more controversial events. Early in the morning on 1st February 1502 the wealthy heiress Margaret Kebell was abducted from Blore Hall in Staffordshire by a band of some one hundred men brandishing swords. Their leader was Sir Richard’s associate Roger Vernon, son of the mighty Sir Henry Vernon of Haddon Hall in Derbyshire, and he wished to marry the lady before her fiancé, Ralph Egerton, managed to do the same. The ceremony was hurriedly performed in Derby before Margaret was bundled off to Vernon’s uncles at Netherseal in Leicestershire and thence down to the Welsh Marches where Sir Richard De la Bere was waiting to confine her at his manor house in Clehonger. She later escaped, though whether or not this was from Clehonger is uncertain, and she returned to her family. A long law suit and years of political wrangling ensued. All the conspirators, including Sir Richard, were technically guilty of felony. He evidently  kept a close eye on the court proceedings, at one stage standing surety for Roger Vernon for two hundred marks. Eventually, however, in December 1509 all were pardoned by the King.