Henry I. bestowed the manor on Geoffrey de Clinton, who built the castle and an adjoining monastery. On the death of Geoffrey it descended to his son, who transferred it to the Crown, probably on himself assuming the cowl of the monk. Henry II. garrisoned it during his son's rebellion.
Henry III. gave Kenilworth to his favourite, Simon de Montfort, whom he had married in 1238 to his sister, the young widow of the great Earl of Pembroke. It was a strange story, that of Princess Eleanor. She had been married in her infancy (four years old) to the Earl of Pembroke, who was forty, when as a bride of fourteen he took her to his home; but she loved him passionately, and when left a widow at the age of sixteen, she was in agonies of grief, and took a solemn vow in the presence of Richard, Archbishop of Canterbury, that she would never marry again, but become the bride of Christ.
Seven years went by, and the beautiful widow's grief passed. She returned to her brother's court, and there met his new favourite, Simon de Montfort, Earl of Leicester in his mother's right, one of the handsomest and most accomplished of the courtiers. The widowed countess forgot her vow, though solemnly warned of the peril of breaking her oath by the primate, and Montfort easily persuaded Henry to give him his sister. But the king knew that both the Church and the barons would violently oppose the match. Much objection had been made to her previous marriage with a subject, though he was the first of the English barons. How then could Henry expect them to agree to a union between a Princess of England and the younger son of a French noble ? They could only be wedded secretly. Therefore it was, that at early dawn, one cold January morning, in the king's private chapel at Windsor, without the presence of any friend but her brother, the daughter of King John was married to De Montfort.
It was not possible, however, to keep the secret long, and when it was divulged, a storm of indignation from priests and peers followed. Henry had recently promised not to transact any business without the assent of the barons, and reproaches were showered upon him by the irate nobles for his broken promise. They took up arms, headed by Prince Richard, the king's brother, and De Montfort had the greatest difficulty, by the exercise of much prudence and ingenuity, to avert the threatened civil war. By bribes and persuasions, however, he dissolved the confederacy, and then he started with all speed for Rome to get a papal dispensation of Eleanor's vow, without which her marriage would always remain illegal. By means of bribes to the papal court and the influence of the Emperor Frederick, who had married Eleanor's sister Isabel, he prevailed in his suit. Meantime Eleanor, who saw that she was locked on with secret scorn, withdrew from court and went to reside in her husband's castle at Kenilworth. How often she must have paced with a sad and anxious heart those ramparts, watching for the coming of him who would be the bearer of tidings either of honour or dishonour to her - her beloved De Montfort.
He came at last, happily before her son was born, and told her that the pope had ordered the papal legate to ratify her marriage The joy must have been as great as the preceding anxiety, and De Montfort kept his Christmas at Kenilworth with regal state that year.
The wedded life of Eleanor was, however, chequered with much sorrow. Her husband soon lost the fickle favour of the king, and she had herself to endure cruel insults on account of her marriage. Then came the baron's wars; her husband opposed to her brother, and at last slain with her first-born son at the battle of Evesham.
Her youngest son, Simon, escaped, and with other fugitives took shelter at Kenilworth. Here he defied both king and legate, and was joined by the friends and followers of those who had fallen at the battle of Evesham. He exercised almost regal authority, sending his officers to drive in cattle and raise contributions for the garrison. But in 1266 the king beleaguered the castle. De Montfort had previously left it, and gone to France to procure succour; but his place was admirably filled by the governor he left in charge, who repulsed every attack of the besiegers. The king then offered terms to the defenders, and also to De Montfort, who had returned and gathered forces in the Isle of Ely.
Meanwhile an assembly of clergy and barons was held at Coventry, and drew up terms of accommodation known as the Dictum de Kenilworth. It provides that the liberties of the Church shall be preserved, and also the great charters, which the king is bound by his oath to keep. It declares that there shall be no disherison, but instead, fines from seven to half a year's rent. The family of De Montfort is excluded from this benefit, and all persons are forbidden, under both civil and spiritual penalties, to circulate stories of vain and foolish miracles done by Simon De Montfort, who was now popularly esteemed a saint and martyr.
The dictum was rejected by the followers of Simon De Montfort; but at length provisions failed at Kenilworth, and a pestilence broke out which obliged the governor to surrender to the king, who immediately bestowed the castle on his youngest son Edward, Earl of Lancaster, afterwards created Earl of Leicester.
"In 1286 a grand chivalric meeting of one hundred knights of high distinction, and the same number of ladies, was held at Kenilworth, and at this festival, it is said, silks were worn for the first time in England." (Timbs.)
The castle came again into the hands of the Crown in the reign of Edward II., who intended to make it an occasional home for himself when desirous of resting from the fatigues of ruling; but the rebellion headed by the queen broke out, he was taken prisoner in Wales, and brought to Kenilworth. Here he was compelled to sign his abdication, and was soon after removed to Berkeley Castle, where he was cruelly murdered in 1327.
The castle frequently passed into the hands of the sovereign till it was bestowed by Queen Elizabeth on her favourite Leicester, who spared no expense in beautifying the fortress, and made splendid additions to it, called after him Leicester's Buildings. It was here the great earl received that celebrated visit from his royal mistress which has been so marvellously described by Scott. To his "Kenilworth" we must refer the reader for it.
On the death of Leicester, Kenilworth went by his will, first to his brother, Ambrose, Earl of Warwick, for his life, and secondly to Leicester's son, Sir Robert Dudley, the child of Lady Douglas Sheffield, daughter of Lord Howard of Effingham, whom the earl had secretly married, but never owned as his wife, and in whose lifetime he actually married the Countess of Essex.
Poor Sir Robert Dudley could never succeed in establishing the legality of his mother's marriage, and obtained leave to go abroad for three years. He was summoned to return, but not obeying the royal mandate, he was pronounced in contempt, and Kenilworth was forfeited to the Crown.
Lord Clarendon is its present possessor, and he has caused the great hall of the castle, Leicester's buildings, and part of the external walls to be repaired and strengthened.
Some of the towers rise seventy feet high, and the ruins being mantled with ivy and situated on an elevated site, are exceedingly picturesque as well as full of romantic and historical associations.