A decorated war hero, he won the Military Cross at the age of 20 during the Great War. He was also a veteran of the Second World War.
He was for some time the editor of Lord Lymington's right-wing journal, the New Pioneer.
After the Second World War he lived in Africa for a short time, after which point he returned to Britain where he established the League of Empire Loyalists in 1954. The League was a pressure group campaigning against the increasing dissolution of the British Empire, and was well-known at the time for its various stunts at Tory Party meetings and conferences (acting as a constant irratation to the party). These stunts included hiding underneath the speaker platform overnight to emerge during the conference in order to put across their points. The League found support from a number of Conservative Party members, although they were disliked very much by the leadership.
He also founded and edited the right-wing magazine Candour. Chesterton went on to co-found the National Front in 1967, an organization that continues to operate today (2003). Chesterton was leader for only a short time, although he made several attempts to keep the party free from national socialist extremists. Upon his stepping down the first of several long, inter-factional disputes took place within the NF which frequently coloured its policies in ways of which Chesterton did not approve. Today the NF describes itself as a "White nationalist organisation founded in 1967 in opposition to multi-racialism and immigration", although the term "multi-racialism" was not in common usage in 1967 (despite Merriam Webster citing 1923 for the first recorded use).
The last 30 years of Chesterton's life were spent in a modest apartment in South Croden with his wife, Doris. He died in 1973 at the age of 77.