Cawley’s father John was a wealthy brewer and thrice mayor of Chichester, leaving sufficient property in and around Chichester for his son to join the gentry. John was keen for Cawley to have an education appropriate for a member of the landed elite and consequently left him £30 a year while he studied at university and the inns of court. He also instructed his son to pay £5 a year for 20 years to the poor of Chichester. It may have been in lieu of this bequest that in 1625 Cawley built an almshouse for 12 decayed tradesmen outside the north gate of the city.
In 1628 Cawley was rewarded for his beneficence by election to the third Caroline Parliament. He made no recorded speeches and his only committee appointment, on 17 May, was for a bill promoted by Lord Bergavenny (Sir Henry Neville II*), whose uncle, Francis Neville I*, lived in Chichester.
In 1630 Cawley compounded for knighthood at £14.
