Still representing the county of Rutland, he was chosen speaker of the House of Commons four times—in 1416, 1417, 1419, and 1422, something unprecedented except in the case of Thomas Chaucer.
In 1416 he was made chief steward of the Duchy of Lancaster estates north of the Trent.
Besides his ancestral manor of Oakham in Rutland, he held estates in Leicestershire.
He had five sons, Thomas, Robert, Roger, John, and William, and two daughters, Anneys and Joan, the latter being married to Sir Henry Plesyngton of Burley in Rutland, grandson of Sir Robert Plesyngton, chief baron of the exchequer in the reign of Richard II.
The family home, called Flore's House, is a prominent listed building on High Street, Oakham.