A devout adherent of the Yorkist affinity, and personal friend of Richard of Gloucester.
In 1481 whilst campaigning on the Scots Borders, Kendall transacted some land on the Manor of Wynsnowe for Richard of Gloucester to his friend and fellow soldier, Sir John Howard.
But later that year he was re-appointed Chief Clerk and Keeper of the Rolls of the King's Bench, so that by the time of Richard III's coup d'état he became Secretary.
[4] On 1 August the Lord Chancellor of England's Great Seal was sent to the Master of Rolls for safe-keeping, by which time Kendal was known to be senior to the Clerks.
Kendal was a prime mover in Richard's regime, a longtime close associate as secretary to the duke of Gloucester.