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Richard was the second son of Sir John De la Bere, a wealthy Welsh landowner, and his wife Agnes, the daughter of Sir Payne Turberville. He may have either been born at his parents home of Weobley Castle on the Gower Peninsula or at Stretford in Herefordshire, around 1320. Little is known of his early life, but he no doubt grew up in the shadow of is elder brother, John, and was lucky to have escaped a life in the church.

At a relatively early age his parents found him an eminently suitable wife. Young Lady Sybil was the only daughter of William De Kynardsley, and thus the sole heiress to her childless brother’s considerable estates centred on Kynardsley (now Kinnersley) Castle in Herefordshire. Richard and Sybil inherited in 1340, and immediately set about obtaining a license to hold a market and a fair in the village. The marriage enabled Richard to live in comfort for the rest of his life, and thus released his father from any further obligation to provide him with lands.

It is unknown how or when Richard first met the Black Prince. He had many influential relatives, particularly in his mother’s family, and one can easily imagine him being presented at court by one cousin or another. However, it should also be remembered that his elder brother, at least, seems to have owned land in Wallingford (Berkshire) where the castle was one of the Prince's major residences. As Prince of Wales, it would be not unnatural for the Black Prince to take an interest in a fellow from his own principality.

The Prince’s Register tells us that by 31st July 1345 Richard was already receiving gifts from the fifteen-year-old Prince - “he gave a ton of wine to Richard De la Bere and Sir Peter De Gildesburgh”; and on 14th January the following year the King himself enlarged an earlier (undated) grant of land to Richard, giving him “Le Nokes” and “Bradewardy” in Herefordshire to add to "Le Bernes" near Cleobury Mortimer in Shropshire.

These notices of Richard’s associations make it highly likely that it was in the Prince's own retinue that he travelled to France in the Summer of 1346, when Edward III decided to press home his claim to the French throne. They landed with the King’s army near Cherbourg and advanced through Normandy towards Rouen. Philip VI of France set out to meet them, and soon the rival hosts were close together, marching on opposite sides of the Seine towards Paris. Edward III, however, found an unguarded ford which his army crossed, and on 25th August they were on the outskirts of the Forest of Crécy. Next day the French arrived on the field, but it was not until the sun had set that the two parties decided to fight.

The action began with an advance of some seven thousand of Philip VI’s crossbowmen, many of them Italian mercenaries. As the maximum distance they could shoot was about a hundred yards, none of them got within range of the first English division before they were cut down by English arrows, and broke. At that point, the French commanders lost whatever control of the battle they had possessed. The leading French division of mounted men-at-arms, furious at the failure and impotence of their bowmen, charged without orders straight at the English lines, riding down their own men, who were crushed beneath the horses. Once through this melee, the French cavalry were still two hundred yards from the English line, and a wave of arrows brought down the front rank of their horses. In the growing darkness, those at the rear of the French army could not see what was happening at the front. The screams of terror and pain coming from the crossbowman and horses convinced them that a general battle had been joined, and all the rear cavalry divisions surged forward, slamming into the first division for the English archers to shoot accurately: they simply aimed at the struggling mass of men and horses in front. Some French men-at-arms, on foot, however, reached the English vanguard, commanded by the Black Prince. This was no doubt when Richard De la Bere took part in the action.

Outnumbered, the young Prince was engaged in fierce hand-to-hand fighting, and at one point was down on his knees. A message was sent to the King for reinforcements; but he would despatch only twenty knights, saying, “Let the boy win his spurs”! By the time they arrived, however, they found the Prince and his men “leaning on lances and swords, taking breath and resting quietly on long mounds of corpses, waiting for the enemy who had withdrawn”.

Was it at this point that Richard saved the Black Prince's life? Before the King’s twenty men were able to claim the same deed? It is quite possible, even probable, that Richard De la Bere, along with several other knights, were able to help the Prince out of this tight spot, for a similar legend to his exists in the Beauchamp family.

In all the French charged fifteen times during the night, and again, with four fresh divisions, at dawn. But the English tactical position was by now unassailable, protected by barriers of French dead, across which the bowmen shot with impunity. Daylight showed an appalling scene of dead and dying horses and men - four thousand knights and “men of superior dignity” were killed, almost all on the French side: “no one troubled to count the others who were slain”.

Family legend implies that Richard was rewarded for his valour on this day with a knighthood and coat of arms. The De la Bere coat of arms is known to have been in use before Richard's time, but he may have been rewarded with the plume of feathers crest, for the Battle of Crécy was traditionally when this badge first became associated with the Prince of Wales. The knighthood seems almost a certainty however. Prior to Crécy, Richard is recorded as simply Richard De la Bere, yet afterwards he quickly becomes “Sir Richard De la Bere, the Prince’s Bachelor, and Constable and Keeper of the Prince's Castle and Lordship of Emlyn”!

Richard had evidently been elevated to the position of a very important man. Emlyn, now Newcastle Emlyn (Dyfed), was one of the Prince’s lordships set up to control the Welsh. From the castle there Richard would have held sway over an area of West Wales the size of the Isle of Wight! What more natural than to give such a lordship to a fellow Welshman? Yet why choose a man from such an obscure noble family, unless he had distinguished himself in some way: by saving the Prince’s life for instance?

From at least 8th February 1347 Richard is recorded as a knight, and his time as Constable of Emlyn probably dates from the January. Nothing can better show the high esteem in which he was held at this time than his new year’s gift from the Black Prince: a buckle of “an ounce of gold with pearls, with a rose in the middle and a crown above it, set with a breast of two birds”.

Sir Richard’s life at Emlyn can be clearly traced, though unfortunately the records mostly tell of mundane day to day duties. The earliest known record orders him to look into a petition to the Prince of Wales from the Abbot of Blanchland and rectify any wrongs done him. Other documents refer to the collecting of debts and the repair of the castle. Indeed it is known that not long after Sir Richard was appointed the castle underwent a major refurbishment, and the defences were enlarged with a double-towered gatehouse and a small polygonal tower. In November 1347 the Prince is seen to request that a weekly market be set up in Emlyn. It was to take place every Thursday, but details such as its location were left up to Sir Richard as “it shall seem best to him”. Several times Sir Richard is ordered to keep the castle at Emlyn “safely guarded” when the Prince had travelled abroad to France, knowing “not how events may shape themselves during his absence”. On another occasion Sir Richard is recorded as having been abroad himself, attending the Prince in Calais in 1352.

Richard’s associations with his home county did not falter, however. He continued to live at Kinnersley when his duties allowed. He was made Sheriff of Herefordshire in 1354, and again in 1356; in between, he attending parliament as the local “Knight of the Shire”. Such an important personage, Sir Richard is probably the member of the De la Bere family about whom most is, or will ever be, known. He died early in 1382, shortly followed by his wife, and they were buried together in the Friary Church of the Dominican Friars in Hereford. Their son and heir, Kynard De la Bere, inherited Kinnersley.