The Fitzsymond family had been established in Essex for about a century, the senior branch holding the manors of Danbury and Langridge, as well as Waterend in Sandridge in Hertfordshire. That branch included Sir Hugh Fitzsymond (the sheriff of 1354-5) and his nephew Sir Edward, who was sheriff in the year of his death, 1375.
In the summer of 1378 Fitzsymond, already a knight, served in the retinue of Sir Aubrey de Vere in the unsuccessful naval expedition led by John of Gaunt against the French fleet, which had been harrying the south coast. His connexion with de Vere was to continue until his death. He was appointed sheriff of Essex and Hertfordshire shortly after his return home, and during his term, in June 1379, he was granted a royal pardon at de Vere’s request for causing the death of one Andrew Bole.
In 1390 Fitzsymond was a feoffee of the manor and advowson of West Thurrock, and as such appeared as co-patron of the prebend of West Thurrock in the royal chapel of Hastings. It is uncertain for whom he was acting.
