John de Radclyffe, son and heir of Richard, was born at Ordsall in 1356, and was twenty-four years old when he succeeded to his inheritance. He lived through the reigns of three monarchs, the disorders of misrule of Richard the Second, the no less lively era of Henry the Fourth, and the valiant awakenings Henry the Fifth inspired. John entered military service at an early age, desiring no doubt to emulate the fame of his grandfather, and was associated with his kinsman, Sir Thomas de Holland, Earl of Kent, half-brother to King Richard. In 1385 he was amongst those chosen by the Earl of Kent to accompany him when he went to take up his appointment as Captain of Cherbourg, and the King's protection was granted to Radclyffe for the safeguarding of his estates during his absence abroad. For some reason his plans were changed; he did not go to Normandy, and the protection was withdrawn. In that year Charles the Sixth of France determined to invade England, and assembled a great army in Flanders, with an armada at the port of Sluys to convey them across. The young King's uncles wisely dissuaded him from the enterprise, and the expedition was abandoned. It is probable that the services of John de Radclyffe were more necessary at home at such a time than they would be overseas. The incompetence of King Richard forced the support of the nation to his uncle, the Duke of Gloucester, whose appointment as head of the Great Council the King was forced to concede. Gradually the power of the Lancastrian party was rising and the Lord of Ordsall was a devoted adherent of that house. John of Gaunt died in 1399, and Richard thereupon seized his immense estates and kept them, notwithstanding his letters patent to the banished Henry of Lancaster permitting him to take possession of his lawful inheritance. According to the Deputy Keeper's Reports, the Radclyffe title to Ordsall was challenged at this time, from which it might appear that Sir John was with Duke Henry in his exile. Within a short time, however, Henry landed at Ravenspur, Richard was deposed, and Lancaster was proclaimed King as Henry the Sixth. Throughout the fourteen years of his reign the new King found Sir John ever a gallant champion of his cause. He fought at Hateley Field, and was amongst those whom King Henry held in constant favour. When Henry the Fifth succeeded his father, Radclyffe like his cousin at Attleburgh was appointed to the personal service of the King, and was given a captaincy in the French war. Though now an elderly man Sir John bore himself with distinction at Agincourt. He was present at the capture of Caen and the Siege of Rouen, and in 1421 was chosen by the King for election to the Order of the Garter. This honour was actually denied him, however, for he died before the Feast of St. George following
About 1375 he married Margaret, daughter of Sir Henry de Trafford, whose manor house faced the hall of Ordsall across the River Irwell. Sir Henry was a considerable landowner of the county, and a notable knight who had won fame in the campaigns of Edward the Third. Margaret bore him a family of four sons and two daughters, and survived her husband. She is said to have been married again, shortly after Sir John's death, to Robert Orrell, of Turton, though she was then past her sixtieth year. In 1413, the year that Henry the Fourth died, Sir John had a dispute with his sons, and agreed to accept the arbitration therein of Ralph de Radclyffe, son of Sir Ralph of Smithills, apparently with successful result
At the death of Sir John it was found that the Rochdale Bailiwick was worth nothing, as the outgoings exceeded the receipts. In 1430 therefore his heir sold the family interest in the bailiwick and serjeancy of Rochdale to Sir John Byron
Sir John and Lady Margaret had issue as follows: