Classics and Div Don
Rupert left the world of private tutoring to return to Winchester in 2018, having been a Collegeman from 2004-2009. He teaches Classics and, his great favourite, first-year Div, as well as coaching football, tennis and Winchester College Football, where he does a valiant job of pretending to know all of the rules.
He and his wife Rosie, also a teacher, have one daughter, Imogen and spend their holidays in vigorous debate about what is an acceptable number of mountains to climb in a week; Rosie tends to win out.
Rupert will take over as Housemaster of Chernocke House when James Fox finishes his term of service in 2025.