Grandson of a UMFC minister, Samuel Chester (1824-1897; e.m. 1860), he was born at Manor Park, London on 25 February 1887. Leaving school at 16, he was a member of Lloyd's for 70 years, being elected an underwriting member in 1914, with his own own syndicate from 1921. From 1926 he served on the Underwriters Association and was its chairman for five years. He was elected to the Committee of Lloyds in 1933, and was Deputy Chairman in 1937 and 1940-1942.
In 1916 he married a school teacher, Winifred Tomkinson, at Manor Park UMFC. and on moving to live in Muswell Hill they joined the WM church there. He led the Senior Department of the Sunday School and was much involved in the youth work, including the church Tennis Club that was started. In 1924 he bought the remainder of the North Bank estate to safeguard these activities and the refurbished site was opened in 1932. In 1947 the estate, with a substantial endowment, was handed over to the Trustees for Methodist Church Purposes and in 1960 Chester House Hostel and the MYD offices, replacing its Ludgate Circus headquarters, were opened on the site, followed by The Meadow MHA in 1967. The bequest of his home, Hazlehyrst, in 1973 completed North Bank Estate as Methodist property.
Deeply committed to young people, he was Treasurer of the Youth Department throughout its existence. His wife was much involved in the work of the YWCA. She died in 1927, following an operation and he commissioned an outstanding series of stained-glass windows for the Muswell Hill church in memory of her.
From 1932 to 1960 he was President of the London Branch of the Methodist Laymen's Missionary Movement (later Methodists for World Mission). He was Vice-President of the Conference in 1954. He was also involved in the League of Nations Union and, in 1945, became president of the Muswell Hill United Nations Association. He was awarded an OBE in 1963. He died at Muswell Hill on 21 October 1973.