Eton College is poised to announce a new headmaster following the planned departure of Simon Henderson in September 2027, marking a rare vacancy at one of the United Kingdom’s most prestigious educational institutions. Henderson, who has led the school for over a decade, disclosed his intention to step down last month, citing a desire to hand over the role after more than ten years at the helm.

The leading candidate to succeed Henderson is Alastair Chirnside, currently serving as headmaster, or warden, of St Edward’s School in Oxford. Chirnside, 50, has been in charge at the co-educational day and boarding school since 2021 and is widely regarded for his leadership within the boarding school community. He is a former King's Scholar at Eton, a distinction awarded to the top scholars, and earned first-class honours at Merton College, Oxford, in classics and French. Before entering education full-time, Chirnside worked as a fund manager in London and held a deputy head position at Harrow School.

Sources familiar with the appointment process have indicated that Chirnside’s experience and reputation make him the frontrunner for the position. Charles Bonas, an educational consultant specialising in elite schooling, noted Chirnside’s strong standing but suggested his current school, St Edward’s, might be reluctant to lose him. Another insider described him as an “absolutely fantastic head” whose credentials align well with Eton’s expectations.

Chirnside’s tenure at St Edward’s has been marked by a return to traditional policies, including the reintroduction of landline telephones in boarding houses and a ban on mobile phones during weekdays for most pupils. He has declined to comment on the potential appointment.

The role of headmaster at Eton carries not only significant responsibility but also public and media scrutiny. The college, located near Windsor, enrolls approximately 1,350 boys and charges annual fees of £63,300, with around 100 pupils receiving full bursaries. Henderson’s salary has reportedly risen from around £265,000 in 2021-22 to approximately £455,000 in 2024-25, reflecting the importance and demands of the post.

While Chirnside is the frontrunner, female candidates have also been interviewed in what would be a historic change for Eton, which has never had a female headmaster in its 586-year history. Such a development would mirror shifts at other elite boys’ schools, such as St Paul’s School in London appointing its first female high master in 2020.

Henderson, who became Eton’s youngest headmaster at age 39, was known for modernising initiatives and faced both praise and criticism for his progressive approach. In a recent letter to parents, he expressed gratitude for his time at the school and confidence in a smooth transition to new leadership.

An official announcement on Henderson’s successor is expected within the coming weeks.