Early Career
Squire was educated at Tiffin Grammar School, Kingston upon Thames and then qualified as a Chartered Accountant while working in a small City practice. He joined the accounting department of Lombard Banking in 1968 (a finance company that became a member of the National Westminster Bank group in 1970) and was promoted to the position of Deputy Chief Accountant at Lombard North Central in 1972. He held this post until he was elected to Parliament in 1979.
During this period he was a Conservative activist. Notably, he held various positions in the Greater London Young Conservatives including that of Chairman in 1973. He was elected a member of Sutton Borough Council in 1968. Squire was the Conservative candidate for Hornchurch in the October 1974 general election although he lost the election by a 7,000 vote margin. In 1976 he become the Leader of Sutton Council.
At an early stage, he demonstrated a political position on the left of the Conservative Party. At the Conservative Party Conference in 1973 he was booed when he opposed a motion calling on the Government to recognise the white minority regime in Rhodesia. At the Conservative Local Government Conference in 1977 Squire was one of five council leaders who spoke against plans advanced by Keith Speed (then Conservative local government spokesman) to abolish the domestic rating system. Squire warned that abolition of the rating system without a widely accepted alternative to put in its place might be highly damaging.
During the period 1970 to 1979, both Conservative and Labour administrations promoted the move to comprehensive education. As Leader of Sutton Council, Squire advocated a move to comprehensive education in the Borough that would be phased in by 1984. However, in 1978 Labour Education Secretary Shirley Williams pressed for an end to selective education in the Borough by 1980. This resulted in a stand-off and Squire threatened legal action against the government in order to prevent an earlier move to comprehensives. The advent of a new Conservative government in May 1979 allowed Sutton to remain as an isolated pocket of selective education and grammar schools. After the Liberal Democrats took control of the Council in 1986 selective education was retained.
Squire was elected to Parliament as the member for Hornchurch on 3 May 1979. Labour-held Hornchurch had not been a marginal seat and Squire had not expected to win it. However, he was elected with a 769 vote majority on a "freak" 8.5% swing. At this point, he stood down as leader of Sutton Borough Council and gave up his Council seat in 1982.
Squire married Susan Fey, a Labour Party activist, in 1981. Questioned about the marriage, Fey stated that she was on the right wing of the Labour Party and her husband was on the left of the Conservative Party. As such, she considered that there was no great political difference between them. The couple had two children (one son and one daughter) by Fey's previous marriage and divorced in 2007.
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