Kynaston was the youngest son of Sir Roger Kynaston (c. 1432/1433–1495), High Sheriff of Shropshire,[3] who was thought to have killed Lord Audley at the Battle of Blore Heath, and Roger's second wife, Lady Elizabeth Grey, daughter of Henry Grey, 2nd Earl of Tankerville and Antigone Plantagenet, the legitimised daughter of Humphrey of Lancaster, 1st Duke of Gloucester (son of Henry IV and Mary de Bohun) and second wife Eleanor de Cobham.
[4] He was raised in Myddle Castle, which Roger had inherited from his first wife Elizabeth Cobham.
[1][6] Kynaston later inherited Myddle Castle from his father, but allowed the estate to fall into disrepair.
[6][11] From 1491 to 1518, Kynaston supposedly lived a life that would match the fictional character Robin Hood.
[2] One time, in an attempt to capture Kynaston, the local sheriff removed several planks from Montford Bridge, to keep him from crossing the River Severn, but his horse managed to leap and safely clear the distance.