Jim Cogan, former deputy head who now teaches English at the Pounds 12, 900 a year school, is the latest in a long line of non-conformists - among them John Locke, Kim Philby, Tony Benn and Nigel Lawson - who have passed through the arches and gates of Dean's Yard since the school gained its charter from Henry VIII in 1560.
He is now taking his radical ideas the short distance to former colleagues and friends in the environs of power to find ministerial funding for a national scheme to encourage pupils to help their local communities through voluntary work. Known as "Changemakers", it has already been taken on by the Secondary Heads Association and Community Service Volunteers and more recently seems to have won the approval of Gillian Shephard - on her visit to the SHA conference at Easter.
Strings are now being pulled by the Chancellor of the Duchy of Lancaster David Hunt (a former school friend from Liverpool College), former education minister Alan Howarth MP (ex-Westminster teacher) and Tim Lankester, a personal friend whose office as Department for Education permanent secretary is one street away. "Although they are all public school and top of the greasy pole, they are concerned to have change underway," explains Mr Cogan.
Changemakers has been billed as an attempt to end the "me first" generation, to put responsibility and concern for others back into education. But Mr Cogan's ideas underpinning the creation of the scheme two years ago would probably surprise even the most iconoclastic of Westminster's scions. According to Mr Cogan, an academically driven Western education undermines the social fabric by concentrating on personal achievement and ignoring obligation to others and social dilemmas; above all, it excises the urge to change anything for the good and adapt to change. That way lies not just a rejected and powerless underclass, but an elite incapable of tackling reforms for anyone's good but their own.
His thinking is inspired by his work in Africa for Schools Partnership Worldwide, a charity he created in 1986 to enable British students to teach in the Third World between school and university when, as he puts it, "they are not being ground down by institutions". Commonly in African schools, pupils share responsibility for cleaning the dormitories and classrooms and preparing the food in self-sustaining co-operation with the teachers and other adults. The Western students learn informally about a more basic kind of life, away from the consumer-driven world.
"Every time I move from a school with every conceivable advantage and which is top of the league tables - for what that's worth - to a school in the heart of Africa, the texture of social relations, the feel the kids give off and their state of physical well-being despite subsistence-living strikes me with a hammer blow.
"If you look at an effete London child with three As and secure job prospects, in a way they are not getting as much out of life as the kid on the margins, because their society is fragmented, not integrated. They have been pulled into a youth spending culture with illusory values." One look at the number of designer training shoes among the shinier and more traditional footwear in Westminster's courtyards proves his point.
Second-guessing critics, he admits an African child would willingly swap places with a Westminster pupil, while acknowledging that in SW1 starvation and disease are not rife and political instability never gets bloodier than stab-in-the-back Parliamentary intrigue. But he adds: "Western education doesn't leave a strong impression of doing anything with what they have learned in the classroom. It gives them a professional qualification to exploit people and charge high fees. The more money they have the meaner they become and the less responsible. Kids lives are impoverished at a very profound level. It would be impossible to explain to an African child that a teenage girl in England has stopped eating and become anorexic."
Elite children suffer as much if not more from the thesis he describes. He cites legal training as an example, learning about crime and law without looking at the causes of crime or how the profession could help reduce it. "Change can only come from young people. The vested interests will never budge: they are mostly elderly men put in controlling positions because they are not interested in change."
Mr Cogan, now 58, did National Service in Nigeria before studying classics and English at Oxford. He then worked in business and taught at the University of the West Indies in Kingston, Jamaica, before going to Westminster in the mid-1960s becoming deputy to John Rae.
With such a background, he is acutely aware of how easy it may sound for him to speak his mind and lecture the maintained sector about responsibility and sense of community from the cloistered position of a major public school. But he equally bemoans the lack of intellectual curiosity and challenging of received ideas that has grown among his pupils since more emphasis has been placed on raw exam success. Protest and diversity of thinking have been usurped by indifference or irrelevant single-issue campaigns. "Children are encouraged to worry about if there are enough blue whales 2,000 miles away, when down the road people are living in appallingly degrading housing."
Step forward Changemakers, which encourages pupils to think about simple local problems and to do something about them. Pilot projects have included running shopping trips for the elderly, improving local parks and converting wasteland. The very process, even if it ends in a "hopeless muddle" according to its founder, teaches skills such as how to influence a local council, or lobby business and community groups for a useful purpose.
Like the African children who must help grow the school's food, Changemakers groups must take charge themselves of both raising and spending funds - a key difference from other projects where adults hold the purse strings. "Inducements to children to spend money start at the school gates and go all the way home. Shouldn't there be an element of children's spending that lets them get closer to social problems?" Experience in Africa shows that when children are given duties towards others, they respond "amazingly", says Mr Cogan. But persuading schools to give up time to allow pupils and teachers to pursue the scheme will be a problem, particularly in the independent sector. "At Westminster, I tried to set up the beginnings of a discussion group to get us more involved with the community and it drew a complete blank. People are too academic or too busy."
It is private schools, dripping with cash and facilities enhanced by charitable status, that could do most to help their local communities, Mr Cogan feels. Peer group teaching, which already takes place in a few independent schools, should be extended, particularly in maths and PE. "The absence of males in primary schools is very disturbing. You have eight-year-olds who have spent their whole lives being mollycoddled by women. That could be offset by having regular use made of particularly sporty boys from secondary school. "
If, as is likely, the Westminster influence helps secure Home Office funding to allow the 300 schools and three LEAs interested in Changemakers to pay for teachers to start the scheme, only the most cynical would begrudge Mr Cogan's anomalous circumstances. Later this month Home Secretary Michael Howard will announce details of Make a Difference, a project backed by the Prime Minister to encourage volunteering in numerous different sectors. With the influence in the right places, Changemakers could be a part of that.
* Changemakers, co CSV Education, 237 Pentonville Road, London N1 9NJ