He was born at Braybrooke, Northamptonshire the son of justiciar Ingebald de Braybrooke and his wife Albreda de Neumarche, daughter of Ivo de Neumarche Lord of Braybrook and Emma de St. Liz.
Le May accumulated more land in several counties by paying off the mortgages of people in financial difficulties.
he was responsible for the building of Braybrooke Castle, a fortified manor house.
He was listed with his son Henry by Roger of Wendover among King John's evil counsellors.
Le May died in 1210 and was succeeded by his eldest son Henry, who also became a sheriff, sometimes sharing the post with his father.