Among the "principal courtiers" who were recipients of this inglorious spoil, Sir John Cheney's name is given as one, and associated with him were Thomas Grey, Marquis of Dorset, William, Lord Hastings, his wife's father-in-law, the King's Chamberlain, and Dr. Thomas Morton, born at Bere-Regis, in Dorset,--then Master of the Rolls, and afterward Cardinal and Archbishop of Canterbury; all west-country names of great interest connected with our little annals. It was however stipulated by his French majesty, after seeing Edward, and swearing the treaty, that John, Lord Howard, and Sir John Cheney, Master of the Horse, should be left as hostages, until the King of England (after receiving the seventy-two thousand crowns) had passed the seas with his army. Edward, after receiving the money, embarked his forces with all expedition, and Howard and Cheney remained until his arrival in England, during which interval they were entertained "very nobly" by the French king.
We do not find him further mentioned during the reign of Edward IV., or the short rule of his unfortunate son, but soon after the usurpation of Richard III., he was among those who gave his adhesion to the Countess of Richmond (mother of Henry VII.) being won over to the interest of her son by her trusty envoy, Sir Reginald Braye, and with him was Sir Giles Daubeney, and other influential men.
This being so, in due time, which occurred almost immediately, in 1483 he joined in the movement--so unfortunate as it turned out--of Henry Stafford, Duke of Buckingham, and was associated with the Courtenays, the Marquis of Dorset, and others forming the western contingent, being in arms against the king, near Salisbury. On the dispersion of Buckingham's followers through the Severn inundation, Sir John Cheney and his companions made their escape safely across to France, where they joined the Earl of Richmond. His name was included in the Proclamation issued against the insurgent fugitives by Richard, with rewards offered therein proportionate to their station, on apprehension.
It is probable Sir John remained with, or near Richmond, in France, until his final expedition to England, in which he doubtless accompanied him, and on landing, proceeded with the Earl's army on their march through Wales to Bosworth.[28]