The second son of a prominent judge, John profited greatly from his father’s will of 1407, through which he received the main family manor of Islingham and other properties in Kent and the Cambridgeshire manor of Ditton Camoys, a settlement made at the expense of Sir William Rickhill’s eldest son and namesake.
While details for much of Rickhill’s early career are lacking, he may have accompanied his unfortunate elder brother, William, to France, where the latter served in the retinue of Humphrey, duke of Gloucester, during the Agincourt campaign. It would appear that he had at least some military experience, since in December 1419 he was one of 12 men named by commissioners in Kent as possessing arms and armour for the defence of the county, a list in which Gloucester’s followers featured strongly.
Like his brothers William and Nicholas, Rickhill was also active at Rochester before the end of Henry V’s reign. In April 1421 John Estwelle made a release to him, Robert Rolleston, keeper of the wardrobe, and Henry de Rowe of a messuage there, almost certainly to the use of the city’s bridge of which de Rowe was a warden;
Earlier, the Rochester connexion played a part in the marriage of John’s daughter, Joan, to the Lancashire lawyer, James Hopwode*, of which Hopwode’s uncle, Bishop Langley, was a prime mover. Langley agreed to pay Rickhill £66 13s. 4d. to secure the match, fixed to take place between 24 July and 2 Nov. 1421.
Following his shrievalty, Rickhill remained a j.p. until March 1429, but he appears otherwise to have retired from local government and an active role in the affairs of Rochester bridge in his later years, possibly because they were plagued by ill health. It was probably in the summer of 1428 that he was named as a feoffee of estates in Sussex and Dorset which Sir Richard Poynings* assigned for the support of his widow, the dowager countess of Arundel, and their children in his will. The connexion with Poynings, a prominent soldier killed at the siege of Orléans the following year, might support the hypothesis that Rickhill himself had earlier pursued a military career. On the other hand, it is equally possible that he and the knight owed their association with each other to Sir Thomas Lewknor*, who served Poynings as a feoffee and was the brother-in-law of Rickhill’s wife, Joan.
Whatever the state of his health, Rickhill had important matters to attend to at the end of his life. In October 1430 he claimed exemption from parliamentary taxation in respect of property in Sussex, probably held in the right of his wife; he did so as a freeman of Winchelsea, revealing an otherwise unknown connexion with that Cinque Port.
Rickhill’s will is no longer extant but he is known to have appointed his widow, Richard Downe of Frindsbury, ‘gentleman’, and two yeomen, Simon Goold of the same parish and John Shamyll of Rochester, as his executors.
