A mercer, Drolle became a freeman of Norwich in 1428-9.
At Norwich, Drolle was an office-holder by 1440, when he became a constable of Wymer ward. The early 1440s were a turbulent time for the city, and he and other leading citizens had formally to submit to the Crown in January 1443, following disturbances directed against Norwich cathedral priory.
Before the end of the same decade, Drolle served a term as one of the sheriffs of Norwich and he had become an alderman by 1452. In May the following year, he was nominated for the office of mayor alongside his former co-sheriff, Richard Brown II*, emerging as the successful candidate. While he was mayor, Queen Margaret of Anjou visited Norwich (perhaps while on pilgrimage to Walsingham to give thanks for her pregnancy), and he was among those who lent money, in his case six marks, towards preparing a suitable reception for her.
After the mid 1450s, Drolle did not hold any major office, other than that of alderman, but he was active in civic affairs for several more years. In 1457, he was one of those chosen to raise a force of 200 men Norwich had agreed to send to the aid of Great Yarmouth, then under threat from enemy naval attacks, and to tax the city’s inhabitants for these soldiers’ costs and wages for eight days.
By now, Drolle was nearing the end of his own life. Dated 10 Jan. 1468, his will was proved on the following 11 Mar.
After Drolle’s death, the Norwich authorities approached Cossey and Agnes about a plan to found a chapel in the guildhall.
