As a baron of Hastings Cobbey claimed exemption from parliamentary subsidies from 1440 onwards. These claims indicate that he had landed holdings at Wilting, Ore and Guestling, near his home Port, and also, as recorded in 1463, substantial moveable goods at the vill of ‘Esthall’ in the hundred of Eastbourne.
Cobbey’s career was focused on Hastings, where he was actively engaged in the administration of the town for over 25 years. Indeed, his fellow Portsmen sent him as their delegate to Brodhulls at Romney on as many as 37 occasions between 1439 and 1465.
That Cobbey was a man to be trusted is suggested by his nomination by Bartholomew Bolney to be a feoffee of the manor of Stonelynk in Fairlight, a duty he fulfilled for 26 years, from 1449 to 1475.
